Thiolates

{
  "id": "MLC-T-CHM-012016",
  "term": "Thiolates",
  "field": "Chemistry",
  "definition": "Anions of the form RS-, formed when a thiol loses its S-H proton, or the salts of such anions, for example sodium methanethiolate. They are excellent nucleophiles because sulfur is large and polarizable, yet they are much weaker bases than alkoxides, since thiols have pKa values near 10 against about 16 for alcohols. A mild base such as sodium hydroxide or potassium carbonate is usually enough to generate them from thiols.",
  "subject": "Organic and Biomolecular Chemistry",
  "see_also": [
    "cation",
    "thiols"
  ],
  "references": [
    "PAC, 1995, 67, 1307. 'Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)' on page 1372 (https://doi.org/10.1351/pac199567081307)"
  ],
  "url": "https://mlchart.com/terminology/chemistry/thiolates/"
}