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Thiocyanate shares its negative charge approximately equally between sulfur and nitrogen. As a consequence, thiocyanate can act as a nucleophile at either sulfur or nitrogen—it is an ambidentate ligand. [SCN] − can also bridge two (M−SCN−M) or even three metals (>SCN− or −SCN<).
Organic thiocyanates are organic compounds containing the functional group RSCN. the organic group is attached to sulfur: R−S−C≡N has a S–C single bond and a C≡N triple bond. [1] Organic thiocyanates are valued building blocks. They allow to access efficiently various sulfur containing functional groups and scaffolds. [2]
Thiocyanate shares its negative charge approximately equally between sulfur and nitrogen. [10] Thiocyanate can bind metals at either sulfur or nitrogen — it is an ambidentate ligand. Other factors, e.g. kinetics and solubility, sometimes influence the observed isomer.
Heteratoms are attacked more easily, and the compound thiocyanates sulfur, nitrogen, and various poor metals. [1]: 241 Thiocyanogen solutions in nonpolar solvents react almost completely with chlorine to give chlorine thiocyanate; but the corresponding bromine thiocyanate is unstable above −50 °C, forming polymeric thiocyanogen and bromine.
Thiocyanate salts are typically prepared by the reaction of cyanide with elemental sulfur: 8 NaCN + S 8 → 8 NaSCN. Sodium thiocyanate crystallizes in an orthorhombic cell. Each Na + center is surrounded by three sulfur and three nitrogen ligands provided by the triatomic thiocyanate anion. [3]
Rhodanese is a mitochondrial enzyme that detoxifies cyanide (CN −) by converting it to thiocyanate (SCN −, also known as "rhodanate"). [1] In enzymatology, the common name is listed as thiosulfate sulfurtransferase (EC 2.8.1.1). [2] The diagram on the right shows the crystallographically-determined structure of rhodanese.
It belongs to mercury thiocyanate structure-type and can be considered a distorted form of the NiBr 2 (CdI 2) structure. Each nickel is octahedrally coordinated by four sulfurs and two nitrogens. The sulfur end of the SCN − ligand is doubly bridging. [1]
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