Thiocyanates
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IUPAC name
cyanosulfanide
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| Other names
sulfocyanate (sulphocyanate), thiocyanide
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3D model (JSmol)
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PubChem CID
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| Properties | |
| SCN- | |
| Molar mass | 58.0824 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
Thiocyanate (also known as rhodanide) is the anion [SCN]−. It is the conjugate base of thiocyanic acid. Common derivatives include the colourless salts potassium thiocyanate and sodium thiocyanate. Organic compounds containing the functional group SCN are also called thiocyanates. Mercury(II) thiocyanate was formerly used in pyrotechnics.
Thiocyanate is analogous to the cyanate ion, [OCN]−, wherein oxygen is replaced by sulfur. [SCN]− is one of the pseudohalides, due to the similarity of its reactions to that of halide ions. Thiocyanate used to be known as rhodanide (from a Greek word for rose) because of the red colour of its complexes with iron. Thiocyanate is produced by the reaction of elemental sulfur or thiosulfate with cyanide:
The second reaction is catalyzed by the enzyme sulfotransferase known as rhodanase and may be relevant to detoxification of cyanide in the body.
Organic and transition metal derivatives of the thiocyanate ion can exist as "linkage isomers". In thiocyanates, the organic group (or metal ion) is attached to sulfur: R−S−C≡N has a S–C single bond and a C≡N triple bond. In isothiocyanates, the substituent is attached to nitrogen: R−N=C=S has a S=C double bond and a C=N double bond:
Organic thiocyanates are valuable building blocks in organic chemistry and they allow to access efficiently various sulfur containing functional groups and scaffolds.
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