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
.
Reactions
Diethyl sulfide is a Lewis base, classified as a
HSAB theory (see also
ECW model). Its relative donor strength toward a series of acids, versus other Lewis bases, can be illustrated by
ECW model.
[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][ The plots shown in this paper used older parameters. Improved E&C parameters are listed in ECW model. ]
With bromine, it forms a salt called diethylbromosulfonium bromide:
A typical coordination complex is cis-, one of many transition metal thioether complexes.
