Thioether

A thioether is a functional group in organosulfur chemistry with the connectivity C–S–C as shown on right. Like many other sulfur-containing compounds, volatile thioethers have foul odors. A thioether is similar to an ether except that it contains a sulfur atom in place of the oxygen. The grouping of oxygen and sulfur in the periodic table suggests that the chemical properties of ethers and thioethers are somewhat similar, though the extent to which this is true in practice varies depending on the application. A thioether is a functional group in organosulfur chemistry with the connectivity C–S–C as shown on right. Like many other sulfur-containing compounds, volatile thioethers have foul odors. A thioether is similar to an ether except that it contains a sulfur atom in place of the oxygen. The grouping of oxygen and sulfur in the periodic table suggests that the chemical properties of ethers and thioethers are somewhat similar, though the extent to which this is true in practice varies depending on the application. Thioethers are sometimes called sulfides, especially in the older literature and this term remains in use for the names of specific thioethers. The two organic substituents are indicated by the prefixes. (CH3)2S is called dimethylsulfide. Some thioethers are named by modifying the common name for the corresponding ether. For example, C6H5SCH3 is methyl phenyl sulfide, but is more commonly called thioanisole, since its structure is related to that for anisole, C6H5OCH3. Thioether is an angular functional group, the C–S–C angle approaching 90°, which is smaller than the C-O-C angle in ether (~110°). The C–S bonds are about 180 pm.