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Diethyl sulfide (
British English British English (BrE, en-GB, or BE) is, according to Lexico, Oxford Dictionaries, "English language, English as used in Great Britain, as distinct from that used elsewhere". More narrowly, it can refer specifically to the English language in ...
: diethyl sulphide) is an organosulfur compound with the chemical formula . It is a colorless, malodorous liquid. Although a common
thioether In organic chemistry, an organic sulfide (British English sulphide) or thioether is an organosulfur functional group with the connectivity as shown on right. Like many other sulfur-containing compounds, volatile sulfides have foul odors. A su ...
, it has few applications.


Preparation

Diethyl sulfide is a by-product of the commercial production of
ethanethiol Ethanethiol, commonly known as ethyl mercaptan, is an organosulfur compound with the formula CH3CH2SH. is a colorless liquid with a distinct odor. Abbreviated EtSH, it consists of an ethyl group (Et), CH3CH2, attached to a thiol group, SH. Its st ...
, 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
potato The potato is a starchy food, a tuber of the plant ''Solanum tuberosum'' and is a root vegetable native to the Americas. The plant is a perennial in the nightshade family Solanaceae. Wild potato species can be found from the southern Unit ...
es.


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 the bromosulfonium salt: : A typical
coordination complex A coordination complex consists of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as '' ligands'' or complexing agents. ...
is ''cis''-PtCl2(SEt2)2.


References

{{reflist, 1 Thioethers Solvents Foul-smelling chemicals