Phenylsulfinates

Phenylsulfinates are a class of organosulfur compounds with the general formula C6H5SO2⁻. They are the salts or esters of phenylsulfinic acid, which has the chemical formula C6H5SO2H. In the salt form, a phenylsulfinate consists of a phenyl group (C6H5) attached to a sulfinate anion (SO2⁻). In ester form, the hydrogen of the sulfinic acid is replaced by an organic group.

Phenylsulfinic acid itself is a relatively strong acid, with a pKa around 2.1. It is a white crystalline solid that is soluble in water and polar organic solvents. Phenylsulfinates can be prepared by various methods, including the reduction of benzenesulfonyl chloride or the oxidation of thiophenol.

The phenylsulfinate anion is a resonance-stabilized species, with the negative charge delocalized between the sulfur atom and the two oxygen atoms. This resonance contributes to the stability of the anion. Phenylsulfinates find applications in organic synthesis as reducing agents, as sources of the phenylsulfinyl group, and in the preparation of other organosulfur compounds. They can also act as ligands in coordination chemistry. Some phenylsulfinate derivatives have been investigated for their biological activities.