Dithiolates

Dithiolates are a class of chemical compounds that contain two thiol groups (SH) attached to a carbon atom or a carbon framework. These functional groups, -SH, are characterized by a sulfur atom bonded to a hydrogen atom. In dithiolates, these two thiol groups can be either on the same carbon atom (geminal dithiolates) or on adjacent carbon atoms (vicinal dithiolates). However, geminal dithiolates are generally unstable and tend to eliminate a molecule of hydrogen sulfide to form a thiocarbonyl compound, such as a thioketone or thioaldehyde. Therefore, vicinal dithiolates are more commonly encountered and studied.

Vicinal dithiolates, where the two thiol groups are on adjacent carbon atoms, are often derived from the reaction of alkenes or alkynes with hydrogen sulfide or other sulfur-containing reagents. These compounds can exist in equilibrium with their cyclic tautomers, known as dithiiranes, which are three-membered rings containing two sulfur atoms. Dithiolates are known for their ability to act as ligands in coordination chemistry, forming stable complexes with various metal ions. The sulfur atoms in the dithiolate moiety can donate electron pairs to the metal center, leading to diverse coordination geometries and chemical properties. These metal dithiolate complexes have found applications in catalysis, materials science, and as models for biological systems involving metal-sulfur interactions. The chemistry of dithiolates is an active area of research, with ongoing investigations into their synthesis, reactivity, and applications.