Disulphide

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In chemistry, a disulfide usually refers to the structural unit composed of a linked pair of sulfur atoms. The disulfide anion is S₂²⁻. The term disulfide can also refer to a chemical compound that contains a disulfide center, such as diphenyl disulfide, C₆H₅S-SC₆H₅.

Sulfur is usually assigned to the reduced oxidation number −2, described as S²⁻ and called sulfide. It has the electron configuration of a noble gas (argon).

In disulfides, sulfur is only reduced to a state with oxidation number −1. Its configuration then resembles that of chlorine and, like it, has the tendency to form a covalent bond with another S⁻ ion to form a disulfide (S₂)²⁻ group. Oxygen can also do this; e.g. in peroxides such as H₂O₂. In many cases, each of the two sulfur atoms in a disulfide group is covalently bonded to a carbon atom in an organic compound, forming a disulfide bond, sometimes called a disulfide linkage or a disulfide bridge. The tendency is a bit more elaborate in the case of sulfur, which can form polysulfides.

Some examples

• Iron disulfide (FeS₂), known as the mineral pyrite.
• Disulfur dichloride (S₂Cl₂), a distillable liquid.
• The amino acid cystine
• The vitamin lipoic acid
• Diphenyl disulfide (Ph₂S₂).

Image:Pyrite-unit-cell-3D-balls.png	Image:Disulfur-dichloride-3D-balls.png	Image:Cystine-3D-balls.png	Image:Lipoic-acid-3D-balls.png	Image:Diphenyl-disulfide-3D-balls.png
FeS2 unit cell	S2Cl2	cystine	lipoic acid	Ph2S2

Misnomers

Disulfide is also used to refer to compounds that contain two sulfide (S²⁻) centers. The compound carbon disulfide, CS₂ is described with the structural formula i.e. S=C=S. This molecule is not a disulfide in the sense that it lacks a S-S bond. Similarly, molybdenum disulfide, MoS₂, is not a disulfide in the sense again that its sulfur atoms are not linked.

Image:Carbon-disulfide-3D-balls.png	Image:Molybdenite-3D-balls.png
CS2	MoS2

See also

• Disulfide bond
• Diphenyl disulfide

References

de:Disulfide

it:Disolfuro ja:ジスルフィド fi:Disulfidi

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Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .