Thiolate

A thiolate is a type of chemical compound. It can mean both the anions made by removing hydrogen from thiols, and any salts that have these ions. The general ch

Thiolate

A thiolate is a type of chemical compound. It can mean both the anions made by removing hydrogen from thiols, and any salts that have these ions. The general chemical formula of a thiolate is RS−.

Thiolates are to thiols what alkoxides are to alcohols. They are the organic derivatives of the bisulfide ion, HS−.

Chemistry

Like alkoxides, thiolates are bases and nucleophiles. Because thiols are stronger acids than alcohols, thiolates are weaker bases than alkoxides.

Nucleophilicity is more complicated, and depends on solvent effects. The sulfur atom is larger than oxygen, which allows the negative charge of the anion to spread out more: thiolate is a softer nucleophile than alkoxide. In a protic solvent, hydrogen bonds attract solvent molecules to the alkoxide anion, which can block it from reacting with an electrophile. These bonds are weaker with the softer thiolate, so in these solutions, thiolates are stronger nucleophiles than alkoxides.

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