thioate

A thioate is a functional group in organic chemistry characterized by a sulfur atom replacing an oxygen atom in an ester or carboxylic acid derivative. The general formula for a thioate can be represented as R-C(=S)-OR' or R-C(=S)-SR'', where R, R', and R'' are organic substituents. When the sulfur atom replaces the oxygen atom of the carbonyl group, the compound is called a thionoester or thionocarboxylate. If the sulfur atom replaces the oxygen atom of the alkoxy or aryloxy group, it is referred to as a thiolester or thiocarboxylate.

Thioates are analogous to their oxygen-containing counterparts and exhibit similar chemical properties, although their reactivity can differ due to the different electronegativity and size of sulfur compared to oxygen. The carbon-sulfur double bond in thionoesters is generally weaker and more polarizable than a carbon-oxygen double bond. Thiolesters, in particular, are important intermediates in biochemistry, playing roles in metabolic pathways such as the citric acid cycle, where acetyl-CoA is a prominent example. The formation and hydrolysis of thioester bonds are often catalyzed by enzymes. The synthesis of thioates can be achieved through various methods, including the reaction of carboxylic acids or their derivatives with thiols or sulfides.