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How do thiols react with bases to form salts?
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organosulfur compound
Examples of organosulfur compounds.
Similar to alcohols, thiols react with alkalies and other bases to form salts.1
Because the sulfur-hydrogen (S–H) bond is weaker than the oxygen-hydrogen (O–H) bond and the larger sulfur atom is better able to disperse the resulting negative charge, thiols are stronger acids than their corresponding alcohols. This acidity allows them to readily form salts when treated with bases. In these reactions, the thiol loses a proton to form a thiolate anion (), which can then function as a base or a ligand in various chemical and biological processes.213