{
  "source": "ORD Dataset Wishlist",
  "snapshot_date": "2026-09-25",
  "ord_wishlist_status_at_snapshot": "Available",
  "ord_wishlist_card": "https://github.com/orgs/open-reaction-database/projects/11?pane=issue&itemId=126569969",
  "ord_data_issue": null,
  "title": "Exploring the chemical space of phenyl sulfide oxidation by automated optimization",
  "doi": "10.1039/D2RE00552B",
  "journal": "Reaction Chem & Eng",
  "publication_date": "2023-01-10",
  "authors": [
    "Pia Mueller",
    "Aikaterini Vriza",
    "Adam D. Clayton",
    "Oliver S. May",
    "Norman Govan",
    "Stuart Notman",
    "Steven V. Ley",
    "Thomas William Chamberlain",
    "Richard A. Bourne"
  ],
  "article_open_access": {
    "status": "hybrid",
    "license": "cc-by"
  },
  "dataset_size_estimate": null,
  "experiment_type": "automated flow",
  "ord_priority": null,
  "ord_difficulty": null,
  "source_data_kind": "unknown",
  "smiles_in_source": "no",
  "needs_author_contact": false,
  "data_locations": [
    {
      "url": "https://doi.org/10.1039/D2RE00552B",
      "what": "React. Chem. Eng. article and RSC-hosted ESI (PDF)",
      "license": "CC-BY 3.0 per Crossref"
    },
    {
      "url": "https://www.repository.cam.ac.uk/handle/1810/346576",
      "what": "Cambridge Apollo record: published version (1.55 MB) and Supporting information (8.25 MB); listing only, SI not downloaded",
      "license": "CC-BY 3.0"
    },
    {
      "url": "https://eprints.whiterose.ac.uk/id/eprint/195226/",
      "what": "White Rose accepted manuscript PDF; confirms 4 sulfides, LHC(9) + Bayesian optimization (BOAEI) per substrate, GC-MS analysis, phosphotungstic acid/H2O2 in flow",
      "license": "CC-BY 3.0"
    }
  ],
  "notes": "Source: Mueller et al., React. Chem. Eng. 2023, 8, 538, doi:10.1039/D2RE00552B (open access, CC-BY 3.0). Open copies with SI are in the Cambridge Apollo repository (doi:10.17863/CAM.93992) and White Rose (eprint 195226). The reaction is automated continuous-flow oxidation of four aryl sulfides to sulfoxides (thioanisole model; diphenyl sulfide used for replicate stability runs; 2-chloroethyl phenyl sulfide as mustard simulant) with H2O2 and phosphotungstic acid. Variables are temperature, residence time, H2O2 equivalents and a fourth continuous parameter. Each substrate got a 9-point Latin hypercube followed by Bayesian optimization (adaptive expected improvement), under 25 experiments per substrate, with online GC-MS analysis (calibrated MS peak areas). Per-experiment results are expected in the ESI (PDF); confirm they are tabulated rather than only plotted before starting. No separate data repository deposit was found. Pitfalls: biphasic (organic/aqueous) steady-state flow. Sulfone and elimination by-products (e.g., allyl phenyl sulfide from the chloroethyl substrate) are only partly quantified. Record the replicate runs as repeats, not new conditions.",
  "verification_caveats": "Steady-state flow self-optimization with algorithm-chosen conditions. Yields come from calibrated GC-MS peak areas; some by-products are unquantified. Whether the ESI tabulates all experiments or only plots them is unverified."
}