Organic sulfide

In organic chemistry, a sulfide (British English sulphide) or thioether is an organosulfur functional group with the connectivity R−S−R' as shown on right.

The grouping of oxygen and sulfur in the periodic table suggests that the chemical properties of ethers and sulfides are somewhat similar, though the extent to which this is true in practice varies depending on the application.

For example, C6H5SCH3 is methyl phenyl sulfide, but is more commonly called thioanisole, since its structure is related to that for anisole, C6H5OCH3.

In terms of their physical properties they resemble ethers, but are less volatile, higher melting, and less hydrophilic.

These properties follow from the polarizability of the divalent sulfur center, which is greater than that for oxygen in ethers.

Sulfides are important in biology, notably in the amino acid methionine and the cofactor biotin.

An unusual but well tested method for the synthesis of thioethers involves addition of alkenes, especially ethylene across the S-Cl bond of sulfur dichloride.

Sulfides undergo hydrogenolysis in the presence of certain metals: Raney nickel is useful for stoichiometric reactions in organic synthesis[11] whereas molybdenum-based catalysts are used to "sweeten" petroleum fractions, in the process called hydrodesulfurization.

[citation needed] Similarly dissolving metal reductions can induce dealkylation or dearylation.