Thioether
Thioether
Thioether (/θaɪˈoʊ.ɛθər/) is a functional group in organic chemistry. It is similar to an ether except that it contains a sulfur atom in place of the oxygen atom present in an ether. Thioethers are a broad class of organic compounds that contain a sulfur atom bonded to two alkyl or aryl groups.
Etymology
The term "thioether" is derived from the Greek word "theion" meaning sulfur and the English word "ether". The prefix "thio-" denotes the replacement of an oxygen atom in a molecule with a sulfur atom.
Structure and Properties
Thioethers are characterized by the presence of a sulfur atom connected to two alkyl or aryl groups. The sulfur atom in a thioether is sp3 hybridized, and the C-S-C bond angle is approximately 100 degrees. Thioethers are generally more reactive than ethers due to the larger size and lower electronegativity of sulfur compared to oxygen.
Synthesis
Thioethers can be synthesized by the reaction of an alkyl halide with a thiolate ion, a process known as alkylation. They can also be prepared by the reaction of a haloalkane with a thiol in the presence of a base.
Uses
Thioethers are used in a variety of applications in organic chemistry. They are used as ligands in coordination chemistry, as protecting groups in organic synthesis, and as sulfur sources in transition metal catalyzed reactions.
Related Terms
- Ether: A class of organic compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups.
- Sulfur: A chemical element with the symbol S and atomic number 16.
- Haloalkane: A class of organic compounds in which one or more hydrogen atoms in an alkane have been replaced by halogen atoms.
- Thiol: An organosulfur compound that contains a carbon-bonded sulfhydryl (-C-SH) group.
External links
- Medical encyclopedia article on Thioether
- Wikipedia's article - Thioether
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