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Diethyl sulfide

Diethyl sulfide

| NFPA-H = 2 | NFPA-F = 3 | NFPA-R = 1 | NFPA-S =

Diethyl sulfide (British English: diethyl sulphide) is an organosulfur compound with the chemical formula . It is a colorless, malodorous liquid. Although a common thioether, it has few applications.

Preparation

Diethyl sulfide is a by-product of the commercial production of ethanethiol, which is prepared by the reaction of ethylene with hydrogen sulfide over an alumina-based catalyst. The amount of diethyl sulfide produced can be controlled by varying the ratio of hydrogen sulfide to ethylene.

Occurrence

Diethyl sulfide has been found to be a constituent of the odor of durian fruit and as a constituent found in volatiles from potatoes.

Reactions

Diethyl sulfide is a Lewis base, classified as a soft ligand (see also ECW model). Its relative donor strength toward a series of acids, versus other Lewis bases, can be illustrated by C-B plots.

With bromine, it forms a salt called diethylbromosulfonium bromide: :

A typical coordination complex is cis-, one of many transition metal thioether complexes.

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References

References

  1. "GESTIS-Stoffdatenbank".
  2. Baldry, Jane. (1972). "Volatile Flavouring Constituents of Durian". Phytochemistry.
  3. Gumbmann, M. R.. (1964). "Food Flavors and Odors, Volatile Sulfur Compounds in Potatoes". Journal of Agricultural and Food Chemistry.
  4. Laurence, C. and Gal, J-F. Lewis Basicity and Affinity Scales, Data and Measurement, (Wiley 2010) pp 50-51 ISBN 978-0-470-74957-9
  5. (1977). "Graphical display of the enthalpies of adduct formation for Lewis acids and bases". Journal of Chemical Education.
  6. Scott A. Snyder, Daniel S. Treitler. (2011). "Synthesis of Et2SBrSbCl5Br and Its Use in Biomimetic Brominative Polyene Cyclizations". Organic Syntheses.
  7. C.Hansson. (2007). "''cis''-Dichloridobis(diethyl sulfide-κ''S'')platinum(II) at 295 and 150 K". Acta Crystallographica Section C.
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thioethers solvents foul-smelling-chemicals ethylthio-compounds
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