SULFONIUM - 2 reference results
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:
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
- Sulfide R-S-R
- Sulfate R-SO4-R
- Sulfite R-SO3-R
- Sulfonate R-SO3−
- Onium compounds
References
External links
- IUPAC definition (short pdf)
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Last updated on Thursday October 09, 2008 at 07:13:49 PDT (GMT -0700)
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