Thioenol

A thioenol is a chemical compound containing a hydroxyl group (-OH) directly bonded to a carbon atom that is also part of a carbon-carbon double bond where one of the carbon atoms forming the double bond also has a thiol substituent (-SH). More specifically, it is an organic compound featuring a hydroxyl group and a thiol group, where the hydroxyl-bearing carbon participates in a carbon-carbon double bond. Thioenols are the sulfur analogues of enols. They are generally unstable and readily tautomerize to their corresponding thioketones or thioaldehydes. The equilibrium typically favors the thioketone/thioaldehyde form. The study of thioenols often involves sterically hindered examples designed to kinetically stabilize the thioenol form, allowing for its characterization. They are of interest in studies of fundamental chemical reactivity and in understanding the properties of sulfur-containing organic molecules.