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A thioether (similar to sulfide) is a functional group in organic chemistry that has the structure R1-S-R2 as shown on right. Like many other sulfur-containing compounds, volatile thioethers characteristically have foul odors.
A thioether is similar to an ether except that it contains a sulfur atom in place of the oxygen. Because oxygen and sulfur belong to the chalcogens group in the periodic table, the chemical properties of ethers and thioethers share some commonalities. This functional group is important in biology, most notably in the amino acid methionine and the cofactor biotin.
Such reactions are accelerated in the presence of base, which converts the thiol into the more nucleophilic thiolate.
Typical oxidants include peroxides.
The heterocyclic compound thiophene is formally a thioether. Because of the aromatic character of this heterocycle, the nonbonding electrons on sulfur, normally responsible for the nucleophilicity so characteristic of thioethers, are delocalized into the π-system. Consequently thiophene exhibits few properties expected for a thioether - thiophene is non-nucleophilic at sulfur and, in fact, is sweet-smelling. Upon hydrogenation, thiophene gives tetrahydrothiophene, C4H8S, which indeed does behave as a typical thioether.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Thioether". A list of authors is available in Wikipedia.|