Diethyl sulfide is an organosulfur compound with the chemical formula (CH3CH2)2S. 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 fruit1 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.34
With bromine, it forms a salt called diethylbromosulfonium bromide:5
(CH3CH2)2S + Br2 → [(CH3CH2)2SBr]+Br−A typical coordination complex is cis-PtCl2(S(CH2CH3)2)2.
References
Baldry, Jane; J. Dougan; G. E. Howard (1972). "Volatile Flavouring Constituents of Durian". Phytochemistry. 11 (6): 2081–2084. Bibcode:1972PChem..11.2081B. doi:10.1016/s0031-9422(00)90176-6. /wiki/Bibcode_(identifier) ↩
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. Bibcode:1964JAFC...12..404G. doi:10.1021/jf60135a004. /wiki/Bibcode_(identifier) ↩
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 ↩
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. doi:10.1021/ed054p612. The plots shown in this paper used older parameters. Improved E&C parameters are listed in ECW model. /wiki/Doi_(identifier) ↩
Scott A. Snyder, Daniel S. Treitler (2011). "Synthesis of Et2SBrSbCl5Br and Its Use in Biomimetic Brominative Polyene Cyclizations". Organic Syntheses. 88: 54. doi:10.15227/orgsyn.088.0054. /wiki/Doi_(identifier) ↩