Sulfoxidi

Sulfoxidi, known in English as sulfoxides, are a class of organosulfur compounds characterized by the sulfoxide functional group, typically described by the formula R–S(=O)–R′. In this group, sulfur is bonded to two carbon substituents and double-bonded to an oxygen atom, giving sulfur an oxidation state of +4. The sulfoxide bond is highly polarized, contributing to distinctive physical and chemical properties.

A notable feature of sulfoxides is the possibility of stereochemistry at the sulfur atom when the two substituents on sulfur are different. This can lead to enantiomeric forms, which is important in fields such as asymmetric synthesis and medicinal chemistry. Sulfoxides generally have higher polarity and boiling points than many sulfides, and many are strong, versatile solvents or reagents. Dimethyl sulfoxide (DMSO) is the simplest and best-known sulfoxide, widely used as a polar aprotic solvent and as a reagent in organic synthesis.

Synthesis of sulfoxides typically involves the controlled oxidation of sulfides (thioethers) using oxidants such as peracids. The oxidation must be carefully stopped at the sulfoxide stage to avoid forming sulfones, which contain two oxygen atoms on sulfur. Common sulfoxides derive from simple sulfides, but more complex sulfoxides occur in natural products and pharmaceuticals.

Applications of sulfoxides are broad. They serve as solvents, intermediates in organic synthesis, and ligands or chiral auxiliaries in catalytic processes. Some drugs and drug metabolites feature sulfoxide moieties, and the sulfoxide group can influence pharmacokinetic and pharmacodynamic properties. In nature and metabolism, sulfide groups can be oxidized to sulfoxides by biological systems, illustrating the chemical relevance of this functional group.