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Why are thiols stronger acids than similar alcohols?
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organosulfur compound
Examples of organosulfur compounds.
Thiols are stronger acids than corresponding alcohols primarily due to two factors:
- Bond Strength: The S–H bond is weaker than the O–H bond, making it easier to break and release a proton.
- Charge Dispersion: The sulfur atom is larger than the oxygen atom, which allows it to better disperse the negative charge that results after the loss of a proton.1
These structural differences also explain why selenols are even stronger acids than thiols, as the trend continues with the even larger selenium atom.1