Diethyl sulfide explained

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^[1] and as a constituent found in volatiles from potatoes.^[2]

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.^{[3] [4]}

With bromine, it forms a salt called diethylbromosulfonium bromide:^[5]

A typical coordination complex is cis-.

Notes and References

1. Baldry . Jane . J. Dougan . G. E. Howard . 1972 . Volatile Flavouring Constituents of Durian . Phytochemistry . 11. 6 . 2081–2084 . 10.1016/s0031-9422(00)90176-6. 1972PChem..11.2081B .
2. Gumbmann . M. R. . H. K. Burr . 1964 . Food Flavors and Odors, Volatile Sulfur Compounds in Potatoes. Journal of Agricultural and Food Chemistry. 12 . 5 . 404–408 . 10.1021/jf60135a004.
3. 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
4. Cramer, R. E. . Bopp, T. T. . 1977. Graphical display of the enthalpies of adduct formation for Lewis acids and bases . Journal of Chemical Education . 54. 612–613. 10.1021/ed054p612. The plots shown in this paper used older parameters. Improved E&C parameters are listed in ECW model.
5. Scott A. Snyder, Daniel S. Treitler. 10.15227/orgsyn.088.0054. Synthesis of Et₂SBrSbCl₅Br and Its Use in Biomimetic Brominative Polyene Cyclizations . Organic Syntheses . 2011 . 88 . 54 .