jia_2025_robowski_hyperspaces.pb.gz

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Jia et al. 2025, Robot-assisted mapping of chemical reaction hyperspaces and networks (Nature)

Dataset description

Robot-generated reaction hyperspaces from Jia, Frydrych, Sobolev et al., Nature 2025 (doi:10.1038/s41586-025-09490-1). One dataset holding six separate screens, each a different reaction template: E1 (Fig. 2a): 774; simple SN1 (Fig. 2b): 832; SN1, Fig. 3: 864; Ugi-type 4-component (Fig. 4): 3234; Hantzsch HPLC 26/80 C (Fig. 5): 62; PBA-catalysed styrene epoxidation (Fig. 6): 756; total 6522 reactions. Built only from the raw measured tables in github.com/yaroslavsobolev/robowski-maps/summary_of_reaction_yield_data (MIT); resampled, postprocessed, interpolated, *_hyvu and model-prediction files were excluded and no row is flagged is_outlier. Yields for the E1, SN1, Ugi-type and PBA screens come from UV-Vis spectral unmixing; Hantzsch yields are replicate-averaged HPLC yields. Amounts are computed from tabulated initial concentrations x reaction volume. Structures were assigned from compound codes using the article and SI.

Decoded from the bound file. This is a read-only preview, not schema validation or scientific verification. Missing values remain unreported; AREA is not relabeled as YIELD.

Location	Record	Inputs and roles	Temperature	Reported measurements	Source
reactions[0]	Record 1	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 77.8178% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[0] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 5.8125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 294.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 122.56896209716797, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 4.146500110626221, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 20.174915313720703, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 82.93103790283203, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.0019 M, [13b] = 0.006666 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid n4CXohdTgVrmpgUMfCXvUN, run simple-reactions/2023-09-14-run01/, plate 61, container 0)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 83.65460205078125 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 77.81780242919922 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[1]	Record 2	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 19.6662% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[1] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 4.125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 209, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 212.72413635253906, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 0.39149999618530273, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 1.9048545360565186, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 78.27586364746094, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.007083 M, [13b] = 0.001734 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid RYV2xCsmufvNTV4XiGxVYw, run simple-reactions/2023-09-14-run01/, plate 61, container 1)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 14.148599624633789 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 19.666200637817383 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[2]	Record 3	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 53.78% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[2] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 2.4375, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 123.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 365.25860595703125, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 0.5619999766349792, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 2.7344272136688232, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 11.241379737854004, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.002266 M, [13b] = 0.002637 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid 5tdEfAQNut3FvVtji2A7mc, run simple-reactions/2023-09-14-run01/, plate 61, container 2)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 53.5093994140625 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 53.779998779296875 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[3]	Record 4	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 79.5521% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[3] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 5.8125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 294.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 146.46551513671875, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 2.9514999389648438, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 14.360608100891113, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 59.034481048583984, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.002127 M, [13b] = 0.008276 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid 8Grm8oJ2T3gVn57GrDWNH3, run simple-reactions/2023-09-14-run01/, plate 61, container 3)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 81.70159912109375 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 79.5521011352539 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[4]	Record 5	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 87.1004% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[4] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 0.75, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 38, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 437.10345458984375, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 1.2450000047683716, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 6.057583332061768, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 24.89655113220215, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.0001801 M, [13b] = 0.001216 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid jdLcFQJZXmwjyWuSgEtP7J, run simple-reactions/2023-09-14-run01/, plate 61, container 4)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 87.99440002441406 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 87.10040283203125 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[5]	Record 6	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 59.7483% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[5] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 5.8125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 294.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 170.36207580566406, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 1.7569999694824219, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 8.548733711242676, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 35.13793182373047, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.00393 M, [13b] = 0.005833 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid 5eTTPtbmLjn2CpNFzZgwZ5, run simple-reactions/2023-09-14-run01/, plate 61, container 5)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 66.1957015991211 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 59.74829864501953 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[6]	Record 7	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 58.7773% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[6] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 2.4375, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 123.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 341.362060546875, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 1.7569999694824219, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 8.548733711242676, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 35.13793182373047, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.000631 M, [13b] = 0.0008997 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid 8TpjT9Gv5Gw74AiGyJHs5a, run simple-reactions/2023-09-14-run01/, plate 61, container 6)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 87.05619812011719 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 58.77730178833008 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[7]	Record 8	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 77.5044% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[7] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 4.125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 209, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 201.2413787841797, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 4.48799991607666, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 21.83649253845215, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 89.75862121582031, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.001611 M, [13b] = 0.005552 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid MQicjCnYV9gYiMUiJzcvQ3, run simple-reactions/2023-09-14-run01/, plate 61, container 7)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 80.466796875 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 77.50440216064453 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[8]	Record 9	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 78.9835% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[8] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 4.125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 209, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 235.37930297851562, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 2.7809998989105225, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 13.531035423278809, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 55.620689392089844, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.001348 M, [13b] = 0.005067 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid jmjf5iS73YFSki7U6WuXTG, run simple-reactions/2023-09-14-run01/, plate 61, container 8)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 83.65879821777344 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 78.9834976196289 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[9]	Record 10	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 79.1015% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[9] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 4.125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 209, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 252.44827270507812, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 1.9275000095367432, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 9.37830638885498, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 38.55172348022461, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.001542 M, [13b] = 0.005836 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid DY7PoHgAXB4zUyJdYEZBkb, run simple-reactions/2023-09-14-run01/, plate 61, container 9)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 81.31099700927734 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 79.10150146484375 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[10]	Record 11	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 59.1609% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[10] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 7.5, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 380, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 71.20689392089844, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 2.439500093460083, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 11.869457244873047, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 48.7931022644043, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.004949 M, [13b] = 0.007169 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid hXk7tm3Q7vrLjCkVr9bU5j, run simple-reactions/2023-09-14-run01/, plate 61, container 10)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 67.0062026977539 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 59.1609001159668 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[11]	Record 12	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 76.8086% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[11] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 2.4375, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 123.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 303.8103332519531, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 3.634500026702881, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 17.68376350402832, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 72.68965148925781, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.001072 M, [13b] = 0.003552 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid BXoSJnNQP32e6ZiWpRrm3J, run simple-reactions/2023-09-14-run01/, plate 61, container 11)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 78.00039672851562 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 76.80860137939453 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[12]	Record 13	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 79.5046% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[12] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 4.125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 209, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 245.62069702148438, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 2.2690000534057617, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 11.039884567260742, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 45.379310607910156, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.001389 M, [13b] = 0.005388 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid VZMeHB2sRWCSpnLxP4ovvG, run simple-reactions/2023-09-14-run01/, plate 61, container 12)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 83.16300201416016 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 79.50460052490234 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[13]	Record 14	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 77.5265% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[13] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 2.4375, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 123.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 293.5689697265625, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 4.146500110626221, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 20.174915313720703, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 82.93103790283203, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.00109 M, [13b] = 0.003761 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid mMAVVTe8MiN8bi5XKdiWhq, run simple-reactions/2023-09-14-run01/, plate 61, container 13)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 77.63600158691406 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 77.52649688720703 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[14]	Record 15	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 32.4745% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[14] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 4.125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 209, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 279.75860595703125, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 0.5619999766349792, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 2.7344272136688232, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 11.241379737854004, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.005037 M, [13b] = 0.002423 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid NnWrwnSX8dnL3Zj9nd37Ue, run simple-reactions/2023-09-14-run01/, plate 61, container 14)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 38.94029998779297 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 32.4744987487793 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[15]	Record 16	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 78.9721% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[15] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 2.4375, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 123.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 351.60345458984375, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 1.2450000047683716, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 6.057583332061768, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 24.89655113220215, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.001019 M, [13b] = 0.003827 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid V9s2Dh8KiBTxkrwNL3gXWm, run simple-reactions/2023-09-14-run01/, plate 61, container 15)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 79.09760284423828 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 78.97209930419922 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[16]	Record 17	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 80.1584% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[16] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 4.125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 209, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 228.55172729492188, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 3.122499942779541, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 15.19261360168457, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 62.44827651977539, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.001453 M, [13b] = 0.005871 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid jDUCyYLnyTDEgTeQmb4vUo, run simple-reactions/2023-09-14-run01/, plate 61, container 16)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 82.38469696044922 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 80.15840148925781 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[17]	Record 18	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 2.9111% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[17] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 5.8125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 294.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 105.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 0.05000000074505806, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 0.2432764321565628, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 100, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.009773 M, [13b] = 0.000293 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid 3uJq5pBoUNTEktQbHziL77, run simple-reactions/2023-09-14-run01/, plate 61, container 17)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 15.928099632263184 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 2.911099910736084 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[18]	Record 19	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 77.8597% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[18] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 2.4375, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 123.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 324.2930908203125, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 2.6105000972747803, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 12.701462745666504, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 52.2068977355957, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.001015 M, [13b] = 0.003571 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid HMCBzAd6nToRa4istvGj99, run simple-reactions/2023-09-14-run01/, plate 61, container 18)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 79.1719970703125 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 77.85970306396484 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[19]	Record 20	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 80.7006% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[19] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 0.75, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 38, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 406.3793029785156, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 2.7809998989105225, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 13.531035423278809, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 55.620689392089844, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.0002798 M, [13b] = 0.00117 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid Y5vNDeVFURk9Pte7XDCSqB, run simple-reactions/2023-09-14-run01/, plate 61, container 19)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 81.34519958496094 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 80.70059967041016 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[20]	Record 21	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 7.5068% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[20] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 7.5, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 380, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 75.86206817626953, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 0.22050000727176666, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 1.0728490352630615, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 44.13793182373047, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.01295 M, [13b] = 0.001051 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid WM9zergmZ268RNSoRnHDPR, run simple-reactions/2023-09-14-run01/, plate 61, container 20)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 13.679800033569336 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 7.506800174713135 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[21]	Record 22	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 56.8456% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[21] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 4.125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 209, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 269.5172424316406, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 1.0740000009536743, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 5.2255778312683105, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 21.482759475708008, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.003472 M, [13b] = 0.004573 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid D6sWmviCm8Q7N4GQkAuKA9, run simple-reactions/2023-09-14-run01/, plate 61, container 21)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 57.91709899902344 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 56.84560012817383 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[22]	Record 23	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 83.1061% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[22] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 0.75, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 38, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 379.0689697265625, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 4.146500110626221, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 20.174915313720703, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 82.93103790283203, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.0002259 M, [13b] = 0.001111 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid Fif2fjXxvgUF5ykB6MusZT, run simple-reactions/2023-09-14-run01/, plate 61, container 22)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 84.93769836425781 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 83.1061019897461 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[23]	Record 24	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 85.5726% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[23] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 0.75, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 38, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 433.6896667480469, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 1.4155000448226929, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 6.887156009674072, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 28.310344696044922, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.000227 M, [13b] = 0.001346 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid RpBb879rDApVGJghvo9Rx4, run simple-reactions/2023-09-14-run01/, plate 61, container 23)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 84.86699676513672 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 85.57260131835938 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[24]	Record 25	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 34.6104% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[24] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 7.5, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 380, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 98.51724243164062, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 1.0740000009536743, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 5.2255778312683105, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 21.482759475708008, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.008426 M, [13b] = 0.00446 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid 7y5AwEKSXVhZVfMUM2T9bu, run simple-reactions/2023-09-14-run01/, plate 61, container 24)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 43.82720184326172 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 34.61040115356445 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[25]	Record 26	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 85.5664% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[25] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 0.75, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 38, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 385.89654541015625, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 3.805000066757202, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 18.513336181640625, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 76.10344696044922, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.0002059 M, [13b] = 0.001221 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid QH4nYcDsFKsPhV5eskRSkx, run simple-reactions/2023-09-14-run01/, plate 61, container 25)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 86.27310180664062 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 85.56639862060547 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[26]	Record 27	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 79.201% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[26] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 2.4375, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 123.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 327.7069091796875, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 2.439500093460083, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 11.869457244873047, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 48.7931022644043, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.0009938 M, [13b] = 0.003784 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid YoLH24rQYNHz8UhtrFZBnj, run simple-reactions/2023-09-14-run01/, plate 61, container 26)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 79.61389923095703 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 79.20099639892578 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[27]	Record 28	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 47.2904% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[27] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 5.8125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 294.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 180.60345458984375, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 1.2450000047683716, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 6.057583332061768, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 24.89655113220215, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.006308 M, [13b] = 0.00566 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid Nhn6MdJC8zqqQWwur2ppMy, run simple-reactions/2023-09-14-run01/, plate 61, container 27)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 45.73379898071289 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 47.290401458740234 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[28]	Record 29	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 26.0007% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[28] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 5.8125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 294.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 194.2586212158203, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 0.5619999766349792, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 2.7344272136688232, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 11.241379737854004, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.007996 M, [13b] = 0.002809 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid 9jszxG5HNFqnTSKAATpiTU, run simple-reactions/2023-09-14-run01/, plate 61, container 28)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 31.217599868774414 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 26.000699996948242 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[29]	Record 30	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 84.4058% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[29] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 0.75, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 38, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 372.24139404296875, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 4.48799991607666, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 21.83649253845215, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 89.75862121582031, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.0002443 M, [13b] = 0.001323 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid 9m6M2oUVNR27w629tDKT2c, run simple-reactions/2023-09-14-run01/, plate 61, container 29)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 83.71019744873047 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 84.40579986572266 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[30]	Record 31	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 70.7986% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[30] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 7.5, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 380, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 60.965518951416016, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 2.9514999389648438, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 14.360608100891113, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 59.034481048583984, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.003649 M, [13b] = 0.008847 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid ZdDnAwHfa4DNkWcmF7vST5, run simple-reactions/2023-09-14-run01/, plate 61, container 30)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 75.67230224609375 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 70.79859924316406 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[31]	Record 32	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 77.8179% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[31] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 4.125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 209, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 208.0689697265625, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 4.146500110626221, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 20.174915313720703, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 82.93103790283203, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.001709 M, [13b] = 0.005995 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid 4qWbHtRR6agUWeS5TyUknM, run simple-reactions/2023-09-14-run01/, plate 61, container 31)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 79.28469848632812 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 77.81790161132812 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[32]	Record 33	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 77.0442% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[32] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 0.75, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 38, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 368.82757568359375, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 4.6585001945495605, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 22.666065216064453, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 93.17241668701172, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.0003102 M, [13b] = 0.001041 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid 6fnJesVk2efnQedL5M5ep4, run simple-reactions/2023-09-14-run01/, plate 61, container 32)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 79.31900024414062 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 77.04419708251953 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[33]	Record 34	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 38.6007% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[33] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 7.5, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 380, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 95.10344696044922, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 1.2450000047683716, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 6.057583332061768, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 24.89655113220215, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.00918 M, [13b] = 0.005771 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid RQoFXMMLkVudgUytnCchpZ, run simple-reactions/2023-09-14-run01/, plate 61, container 33)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 38.79999923706055 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 38.60070037841797 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[34]	Record 35	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 57.0911% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[34] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 7.5, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 380, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 78.03448486328125, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 2.0985000133514404, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 10.210311889648438, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 41.965518951416016, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.005022 M, [13b] = 0.006682 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid Exue5r6iUurXp2xvFTenRp, run simple-reactions/2023-09-14-run01/, plate 61, container 34)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 66.52100372314453 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 57.09109878540039 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[35]	Record 36	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 78.4211% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[35] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 2.4375, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 123.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 276.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 5, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 24.32764434814453, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 100, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.0009712 M, [13b] = 0.00353 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid cQDPB6SJJp45JesUhHiwWr, run simple-reactions/2023-09-14-run01/, plate 61, container 35)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 80.07710266113281 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 78.42109680175781 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[36]	Record 37	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 83.4435% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[36] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 0.75, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 38, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 399.5517272949219, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 3.122499942779541, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 15.19261360168457, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 62.44827651977539, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.0002329 M, [13b] = 0.001174 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid 5kpqH4kPXApQJRgFqS8gzL, run simple-reactions/2023-09-14-run01/, plate 61, container 36)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 84.47010040283203 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 83.44349670410156 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[37]	Record 38	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 78.3058% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[37] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 4.125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 209, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 211.48275756835938, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 3.9760000705718994, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 19.3453426361084, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 79.51724243164062, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.001387 M, [13b] = 0.005005 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid 8VXV5gfUsss6kgr4bomLpE, run simple-reactions/2023-09-14-run01/, plate 61, container 37)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 83.19129943847656 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 78.30580139160156 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[38]	Record 39	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 12.8862% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[38] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 4.125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 209, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 246.86207580566406, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 0.22050000727176666, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 1.0728490352630615, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 44.13793182373047, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.006222 M, [13b] = 0.0009204 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid KowhAkFiv9FQ6moHeesnAx, run simple-reactions/2023-09-14-run01/, plate 61, container 38)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 24.579999923706055 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 12.886199951171875 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[39]	Record 40	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 15.1109% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[39] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 5.8125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 294.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 127.22413635253906, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 0.39149999618530273, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 1.9048545360565186, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 78.27586364746094, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.008557 M, [13b] = 0.001523 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid S9WVACcfPcu25AgHP29U3S, run simple-reactions/2023-09-14-run01/, plate 61, container 39)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 26.38960075378418 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 15.110899925231934 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[40]	Record 41	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 79.5922% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[40] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 5.8125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 294.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 129.39654541015625, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 3.805000066757202, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 18.513336181640625, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 76.10344696044922, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.002144 M, [13b] = 0.008362 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid Zn2DNExVEN5p2hKVWb7kmg, run simple-reactions/2023-09-14-run01/, plate 61, container 40)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 81.55560302734375 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 79.59220123291016 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[41]	Record 42	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 67.9007% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[41] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 0.75, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 38, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 383.7241516113281, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 0.39149999618530273, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 1.9048545360565186, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 78.27586364746094, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.0005838 M, [13b] = 0.001235 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid Madh98uYpd4wnSDR3WxL7D, run simple-reactions/2023-09-14-run01/, plate 61, container 41)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 61.0817985534668 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 67.90070343017578 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[42]	Record 43	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 81.1017% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[42] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 7.5, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 380, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 47.31034469604492, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 3.634500026702881, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 17.68376350402832, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 72.68965148925781, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.002456 M, [13b] = 0.01054 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid KvYBcXpfGfrDic5qNHU5yr, run simple-reactions/2023-09-14-run01/, plate 61, container 42)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 83.62969970703125 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 81.10169982910156 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[43]	Record 44	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 79.1465% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[43] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 2.4375, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 123.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 331.1206970214844, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 2.2690000534057617, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 11.039884567260742, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 45.379310607910156, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.001155 M, [13b] = 0.004385 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid 6mWM74rWcnmDap2jqanbXU, run simple-reactions/2023-09-14-run01/, plate 61, container 43)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 76.29869842529297 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 79.14649963378906 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[44]	Record 45	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 84.3519% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[44] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 0.75, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 38, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 426.862060546875, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 1.7569999694824219, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 8.548733711242676, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 35.13793182373047, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.0002511 M, [13b] = 0.001354 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid g828bfogKoWetvd965BGzD, run simple-reactions/2023-09-14-run01/, plate 61, container 44)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 83.2572021484375 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 84.35189819335938 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[45]	Record 46	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 2.8776% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[45] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 4.125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 209, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 191, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 0.05000000074505806, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 0.2432764321565628, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 100, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.007263 M, [13b] = 0.0002152 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid fKgNLtSqPzK9SoQRv4YcQ6, run simple-reactions/2023-09-14-run01/, plate 61, container 45)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 11.96500015258789 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 2.8775999546051025 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[46]	Record 47	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 79.1847% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[46] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 5.8125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 294.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 115.74137878417969, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 4.48799991607666, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 21.83649253845215, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 89.75862121582031, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.001828 M, [13b] = 0.006954 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid 6VTBHTV7BbeY7QvbpUtzwF, run simple-reactions/2023-09-14-run01/, plate 61, container 46)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 84.27469635009766 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 79.18470001220703 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[47]	Record 48	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 79.7352% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[47] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 7.5, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 380, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 37.068965911865234, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 4.146500110626221, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 20.174915313720703, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 82.93103790283203, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.00225 M, [13b] = 0.008853 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid 7CBThcqLqTeLpcaHwLTuFC, run simple-reactions/2023-09-14-run01/, plate 61, container 47)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 85.00019836425781 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 79.73519897460938 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[48]	Record 49	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 78.3194% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[48] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 5.8125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 294.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 105.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 5, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 24.32764434814453, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 100, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.002101 M, [13b] = 0.007591 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid mLoy6N4rXF7r9FSkACdGWE, run simple-reactions/2023-09-14-run01/, plate 61, container 48)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 81.92440032958984 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 78.31939697265625 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }
reactions[49]	Record 50	REACTANT: 9-butyl-9H-fluoren-9-ol SOLVENT: acetonitrile SOLVENT: acetonitrile REAGENT: hydrogen bromide SOLVENT: water SOLVENT: acetonitrile	26 CELSIUS	9-butylidene-9H-fluorene · YIELD: 81.3855% [UV-Vis]	10.1038/s41586-025-09490-1
Decoded fields · reactions[49] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_CXSMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21>Br.CC#N>CCCC=C1c2ccccc2-c2ccccc21", "is_mapped": false } ], "inputs": { "13a stock (19.7 mM in MeCN)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC1(O)c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butyl-9H-fluoren-9-ol" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13a / E1OH02" } ], "amount": { "moles": { "value": 5.8125, "units": "MICROMOLE" } }, "reaction_role": "REACTANT", "is_limiting": true }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 294.5, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "acetonitrile": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 143.05172729492188, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 1, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } }, "HBr stock (48% aq. HBr diluted in MeCN to 50, 5 or 0.5 mM)": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Br" }, { "type": "NAME", "value": "hydrogen bromide" } ], "amount": { "moles": { "value": 3.122499942779541, "units": "MICROMOLE" } }, "reaction_role": "REAGENT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "moles": { "value": 15.19261360168457, "units": "MICROMOLE" } }, "reaction_role": "SOLVENT" }, { "identifiers": [ { "type": "SMILES", "value": "CC#N" }, { "type": "NAME", "value": "acetonitrile" } ], "amount": { "volume": { "value": 62.44827651977539, "units": "MICROLITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "Hamilton ZEUS automated pipetting module" } } }, "setup": { "vessel": { "type": "VIAL", "details": "2-mL glass vial in a custom 54-well plate, sealed with rubber/PFA sheet and flat lid", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": true, "automation_platform": "Custom robotic platform (Hamilton ZEUS pipetting, NanoDrop/CRAIC UV-Vis)" }, "conditions": { "temperature": { "control": { "type": "CUSTOM", "details": "Thermostatic oven" }, "setpoint": { "value": 26, "units": "CELSIUS" } }, "stirring": { "type": "AGITATION", "details": "Orbital shaker 250 rpm for 5 min after sealing, then left without stirring (passive mixing) in a thermostatic oven" }, "conditions_are_dynamic": false }, "notes": { "is_sensitive_to_moisture": false, "procedure_details": "E1 elimination of 9-butyl-9H-fluoren-9-ol (13a) to 9-butylidene-9H-fluorene (13b) with HBr in acetonitrile (main text Fig. 2a; SI Section 4.2.2). Stocks: 13a 19.7 mM in MeCN; 48% aqueous HBr diluted in MeCN to 50 mM (vol#HBr), 5 mM (vol#HBr_dil_x_10) and 0.5 mM (vol#HBr_dil_x_100). Addition order MeCN, 13a, HBr; total volume 500 uL. Sealed, shaken 5 min at 250 rpm, kept 4 h in a thermostatic oven, then diluted 30x and UV-Vis spectrum recorded (NanoDrop). Amounts are computed from the tabulated initial concentrations (c#) x 500 uL; water amount estimated from the 48 wt% HBr composition. Measured crude concentrations: [13a] = 0.002184 M, [13b] = 0.00955 M. Yield as defined by the authors' processing script: [13b]/([13b] + [13a]) after reaction.\n\nSource row: https://github.com/yaroslavsobolev/robowski-maps/tree/main/summary_of_reaction_yield_data/E1/raw_yields.csv (uuid 37GSRNoJ7bPCJKhsFczhk5, run simple-reactions/2023-09-14-run01/, plate 61, container 49)." }, "workups": [ { "type": "CUSTOM", "details": "Sampling for analysis: automated 30x dilution with acetonitrile before UV-Vis" } ], "outcomes": [ { "reaction_time": { "value": 4, "units": "HOUR" }, "conversion": { "value": 81.21050262451172 }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=C1c2ccccc2-c2ccccc21" }, { "type": "NAME", "value": "9-butylidene-9H-fluorene" }, { "type": "CUSTOM", "details": "compound code used in the source data / article", "value": "13b / E1DB02" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "UV-Vis", "type": "YIELD", "uses_internal_standard": false, "uses_authentic_standard": true, "percentage": { "value": 81.385498046875 } } ], "reaction_role": "PRODUCT" } ], "analyses": { "UV-Vis": { "type": "UV", "details": "UV-Vis absorption spectrum of the diluted crude mixture, concentrations obtained by spectral unmixing against reference spectra of HPLC-purified components (SI Sections 3 and 3.10, Tables S4/S6); NanoDrop, 30x dilution", "is_of_isolated_species": false } } } ], "provenance": { "experimenter": { "name": "Yankai Jia" }, "doi": "10.1038/s41586-025-09490-1", "publication_url": "https://doi.org/10.1038/s41586-025-09490-1", "record_created": { "time": { "value": "2026-10-14" }, "person": { "username": "jordan", "name": "Jordan", "email": "curator@example.org" } } } }