Thioether

Thioether is a functional group in organic chemistry. Thioethers are analogues of ethers in which one oxygen atom has been replaced with a sulfur atom. The general structure of a thioether is R-S-R', where R and R' are any organic groups. They can be classified into simple thioethers, cyclic thioethers, and aromatic thioethers.

Structure and Bonding

Thioethers are characterized by the R-S-R' functional group. The sulfur atom is typically sp3 hybridized and has a tetrahedral geometry. The C-S-C bond angle is slightly less than 109.5 degrees, which is the ideal bond angle for a tetrahedral geometry. The C-S bond length is typically around 1.82 Å.

Preparation

Thioethers can be prepared by several methods. One common method is the reaction of a halide with a thiol. Another method is the alkylation of thiourea, followed by hydrolysis. Thioethers can also be prepared by the reaction of a metal sulfide with an alkyl halide.

Reactions

Thioethers are relatively stable compounds, but they can undergo a number of reactions. They can be oxidized to sulfoxides and then to sulfones. They can also undergo alkylation to form new thioethers. In the presence of a strong base, thioethers can undergo alpha-elimination to form alkenes and a sulfide.

Applications

Thioethers are used in a variety of applications. They are used as ligands in coordination chemistry, as building blocks in organic synthesis, and as odorants in the food and fragrance industry. Some thioethers are also used as drugs, such as the antipsychotic drug thiothixene.

See Also

• Ether
• Sulfide
• Sulfoxide
• Sulfone
• Thiol
• Thiourea

References

Thioether Resources
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