Selenosulfide
chemical compounds containing sulfur and selenium
In chemistry, a selenosulfide refers to distinct classes of inorganic and organic compounds containing sulfur and selenium. The organic derivatives contain Se-S bonds, whereas the inorganic derivatives are more variable.
Organic selenosulfides
These species are classified as both organosulfur and organoselenium compounds. They are hybrids of organic disulfides and organic diselenides.
Preparation, structure, and reactivity
Selenosulfides have been prepared by the reaction of selenyl halides with thiols:
RSeCl + R'SH → RSeSR' + HCl
The equilibrium between diselenides and disulfides lies on the left:
RSeSeR + R'SSR'
↽
−
⇀
{\displaystyle {\ce {<<=>}}}
2 RSeSR'
Because of the facility of this equilibrium, many of the best characterized examples of selenosulfides are cyclic, whereby S-Se bonds are stabilized intramolecularly. One example is the 1,8-selenosulfide of naphthalene. The selenium-sulfur bond length is about 220 picometers, the average of a typical S-S and Se-Se bond.
Occurrence
Selenosulfide groups can be found in almost all living organisms as part of various peroxidase enzymes, such as glutathione peroxidase and thioredoxin reductase. They are formed by the oxidative coupling of selenocysteine and cysteine residues. This reaction is powered by the decomposition of cellular peroxides, which can be highly damaging and a source of oxidative stress.
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