Trimethylselenonium iodide
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| IUPAC name
Trimethylselanium iodide[1]
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| [(CH3)3Se]I | |
| Molar mass | 250.980 g·mol−1 |
| Appearance | White crystalline solid |
| Melting point | 157.7 °C (315.9 °F; 430.8 K) |
| Structure | |
| Orthorombic[2] | |
| Trigonal pyramidal at Se | |
| Related compounds | |
Related compounds
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Trimethylsulfonium iodide |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Trimethylselenonium iodide is an ionic compound with the chemical formula [(CH3)3Se]I. It is the selenium analogue of trimethylsulfonium iodide. It is white crystalline solid. Its structure is [(CH3)3Se]+I−, consisting of trimethylselenonium cations [(CH3)3Se]+ and iodide anions I−.
History
Trimethylselenonium iodide was the first known selenonium compound, discovered by Charles Loring Jackson during his early work on organoselenium compounds;[3] its existence was predicted earlier by Auguste André Thomas Cahours.[4][5]
Preparation
Jackson's preparation of trimethylselenonium iodide used benzyl diselenide and methyl iodide. The reaction produced white crystals identified as trimethylselenonium iodide, with benzyl iodide and benzyldimethylselenonium triiodide as byproducts. Per Jackson, the reaction is:[4]
- (C6H5CH2)2Se2 + 5 CH3I → [(CH3)3Se]+I− + [(C6H5CH2)(CH3)2Se]+[I3]− + C6H5CH2I
It may also be prepared directly by methylation of dimethyl selenide by methyl iodide:[6]
- (CH3)2Se + CH3I → [(CH3)3Se]+I−
This preparation is analogous to the production of trimethylsulfonium halides from dimethyl sulfide.
Uses
Trimethylselenonium iodide is used as a primary standard compound in analytical method development and in basic and environmentally related studies.[6]
Sources
- ^ PubChem. "Trimethylselenonium iodide". Retrieved 2026-03-03.
- ^ Hope, H. (May 10, 1966). "The crystal structure of trimethylselenonium iodide, (CH3)3SeI". Acta Crystallographica. 20 (5): 610–613. doi:10.1107/S0365110X66001488. ISSN 0365-110X.
- ^ Leicester, Henry M.; Bergstrom, F. W. (1929). "Salts of Triphenylselenonium Hydroxide". Journal of the American Chemical Society. 51 (12): 3587–3591. doi:10.1021/ja01387a011.
- ^ a b Jackson, C. L. (1875). "Certain methyl and benzyl compounds containing selenium". American Journal of Science (56): 139–146. doi:10.2475/ajs.s3-10.56.139.
- ^ Cahours, A. (1865). "Untersuchungen über die organischen Radicale". Justus Liebigs Annalen der Chemie. 135 (3): 352–357. doi:10.1002/jlac.18651350313.
- ^ a b Zhao, Qiu-Xiang; Chen, Yu-Wei; Montaut, Sabine; Joly, Helen A.; Wang, Mohui; Belzile, Nelson (October 1, 2010). "Synthesis, identification and chemical features of high-purity trimethylselenonium iodide". Journal of Sulfur Chemistry. 31 (5): 373–385. doi:10.1080/17415993.2010.516435. ISSN 1741-5993.