Dimethyl selenide explained

Dimethyl selenide is the organoselenium compound with the formula (CH₃)₂Se. This colorless, malodorous, liquid is the simplest selenoether. It occurs in trace amounts in anaerobic environments^[1] and in the atmosphere due to biomethylation of selenium.^{[2] [3]}

Dimethyl selenide is prepared by treating Se²⁻ sources with electrophilic methylating agents such as methyl iodide:

Na₂Se + 2 CH₃I → (CH₃)₂Se + 2 NaI

The carbon–selenium bond length is 1.943 Å and the C–Se–C bond angle is 96.2°, as determined by microwave spectroscopy.^{[4] [5]} Similar dimensions of 1.98 Å and 98° are found by gas electron diffraction.^{[6] [7]}

Notes and References

1. Production of volatile derivatives of metal(loid)s by microflora involved in anaerobic digestion of sewage sludge. Michalke, K. . Wickenheiser, E. B. . Mehring, M. . Hirner, A. V. . Hensel, R. . Applied and Environmental Microbiology. 2000. 66. 7. 2791–2796. 10.1128/AEM.66.7.2791-2796.2000. 92074. 10877769. 2000ApEnM..66.2791M.
2. Biomethylation of Selenium and Tellurium: Microorganisms and Plants . Thomas G. . Chasteen . Ronald . Bentley . . 2003 . 103 . 1 . 1–26 . 10.1021/cr010210+ . 12517179 .
3. Kinetics of the atmospherically important reactions of dimethyl selenide . Roger . Atkinson . Sara M. . Aschmann . David . Hasegawa . Elisabeth T. . Thompson-Eagle . William T. . Frankenberger Jr. . . 1990 . 24 . 9 . 1326–1332 . 10.1021/es00079a005 . 1990EnST...24.1326A .
4. Book: . 97th . . 2016 . William M. Haynes . 9–41 . 978-1498754293.
5. James F. . Beecher . Microwave spectrum, dipole moment, structure, and internal rotation of dimethyl selenide . . 1966 . 21 . 1–4 . 414–424 . 10.1016/0022-2852(66)90165-2 . 1966JMoSp..21..414B .
6. Book: A. F. . Wells . Structural Inorganic Chemistry . 5th . 1984 . Oxford University Press . 978-0-19-965763-6 . 705 .
7. An Electron Diffraction Investigation of Dimethyl Selenide . Elihu . Goldish . Kenneth . Hedberg . Richard E. . Marsh . Verner . Schomaker . . 1955 . 77 . 11 . 2948–2949 . 10.1021/ja01616a005 .