Dimethyl selenide

Last updated
Dimethyl selenide
Dimethylselenide.svg
Dimethyl-selenide-from-MW-3D-bs-17.png
Names
Preferred IUPAC name
(Methylselanyl)methane
Other names
methylselenide
Identifiers
3D model (JSmol)
1696848
ChEBI
ECHA InfoCard 100.008.918 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-807-4
KEGG
PubChem CID
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
Appearancecolorless 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:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
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]

Related Research Articles

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Tellurium is a chemical element; it has symbol Te and atomic number 52. It is a brittle, mildly toxic, rare, silver-white metalloid. Tellurium is chemically related to selenium and sulfur, all three of which are chalcogens. It is occasionally found in its native form as elemental crystals. Tellurium is far more common in the Universe as a whole than on Earth. Its extreme rarity in the Earth's crust, comparable to that of platinum, is due partly to its formation of a volatile hydride that caused tellurium to be lost to space as a gas during the hot nebular formation of Earth.

<span class="mw-page-title-main">Ethane</span> Organic compound (H3C–CH3)

Ethane is a naturally occurring organic chemical compound with chemical formula C
2
H
6
. At standard temperature and pressure, ethane is a colorless, odorless gas. Like many hydrocarbons, ethane is isolated on an industrial scale from natural gas and as a petrochemical by-product of petroleum refining. Its chief use is as feedstock for ethylene production.

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In organic chemistry, a sulfoxide, also called a sulfoxide, is an organosulfur compound containing a sulfinyl functional group attached to two carbon atoms. It is a polar functional group. Sulfoxides are oxidized derivatives of sulfides. Examples of important sulfoxides are alliin, a precursor to the compound that gives freshly crushed garlic its aroma, and dimethyl sulfoxide (DMSO), a common solvent.

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In organic chemistry, thioketones are organosulfur compounds related to conventional ketones in which the oxygen has been replaced by a sulfur. Instead of a structure of R2C=O, thioketones have the structure R2C=S, which is reflected by the prefix "thio-" in the name of the functional group. Thus the simplest thioketone is thioacetone, the sulfur analog of acetone. Unhindered alkylthioketones typically tend to form polymers or rings.

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<span class="mw-page-title-main">Dimethylphenylphosphine</span> Chemical compound

Dimethylphenylphosphine is an organophosphorus compound with a formula P(C6H5)(CH3)2. The phosphorus is connected to a phenyl group and two methyl groups, making it the simplest aromatic alkylphosphine. It is colorless air sensitive liquid. It is a member of series (CH3)3-n(C6H5)2P that also includes n = 0, n = 2, and n = 3 that are often employed as ligands in metal phosphine complexes.

<span class="mw-page-title-main">Sodium selenide</span> Chemical compound

Sodium selenide is an inorganic compound of sodium and selenium with the chemical formula Na2Se.

<span class="mw-page-title-main">Hexamethylbenzene</span> Chemical compound

Hexamethylbenzene, also known as mellitene, is a hydrocarbon with the molecular formula C12H18 and the condensed structural formula C6(CH3)6. It is an aromatic compound and a derivative of benzene, where benzene's six hydrogen atoms have each been replaced by a methyl group. In 1929, Kathleen Lonsdale reported the crystal structure of hexamethylbenzene, demonstrating that the central ring is hexagonal and flat and thereby ending an ongoing debate about the physical parameters of the benzene system. This was a historically significant result, both for the field of X-ray crystallography and for understanding aromaticity.

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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+.
  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. 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: 414–424. 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.