AskDefine | Define sulfonium

User Contributed Dictionary

English

Noun

sulfnium
  1. the univalent H3S+ cation, derived from sulfane

Extensive Definition

A sulfonium ion, also known as sulphonium ion and sulfanium ion, is a positively charged sulfur ion carrying three alkyl groups as substituents (S+R3). Ionic compounds consisting of a positively charged sulfonium cation and a negatively charged anion are called sulfonium salts.
Sulfonium compounds can be synthesized from the reaction of dialkylsulfides with alkyl halides:
CH3-S-CH3 + CH3-I → (CH3)3S+ I− (trimethylsulfonium iodide)
In the above reaction, the alkylation of a sulfide, the sulfur atom has two lone electron pairs. Using those lone pairs, the sulfide acts as a nucleophile, and attacks the carbon of iodomethane. At the same time, as part of a concerted nucleophilic substitution mechanism (SN2), the iodide leaving group comes off; this leaves a positively charged trimethylsulfonium ion. This cation is attracted to the negatively charged iodide, so the two form an ionic bond, giving trimethylsulfonium iodide.

See also

References

External links

sulfonium in German: Sulfonium
sulfonium in Japanese: スルホニウム
sulfonium in Portuguese: Sulfônio
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