Dimethyl selenide

Dimethyl selenide
Names
Preferred IUPAC name
(Methylselanyl)methane
Other names
methylselenide
Identifiers
3D model (JSmol)
1696848
ChEBI
ECHA InfoCard 100.008.918 Edit this at Wikidata
EC Number
  • 209-807-4
KEGG
UNII
  • InChI=1S/C2H6Se/c1-3-2/h1-2H3
    Key: RVIXKDRPFPUUOO-UHFFFAOYSA-N
  • C[Se]C
Properties
C2H6Se
Molar mass 109.041 g·mol−1
Appearance colorless liquid
Density 1.4077 g/cm3 (14.6 °C)
Melting point −87.2 °C (−125.0 °F; 186.0 K)
Boiling point 55 °C (131 °F; 328 K)
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Warning
H301, H331, H373, H410
P260, P261, P264, P270, P271, P273, P301+P310, P304+P340, P311, P314, P321, P330, P391, P403+P233, P405, P501
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

References

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

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