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Cyanide

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Cyanide

In chemistry, cyanide (from Greek kyanos 'dark blue') is an inorganic chemical compound that contains a CN functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom.

Ionic cyanides contain the cyanide anion C≡N. This anion is extremely poisonous. Soluble cyanide salts such as sodium cyanide (NaCN), potassium cyanide (KCN) and tetraethylammonium cyanide ([(CH3CH2)4N]CN) are highly toxic.

Covalent cyanides contain the −C≡N group, and are usually called nitriles if the group is linked by a single covalent bond to carbon atom. For example, in acetonitrile CH3−C≡N, the cyanide group is bonded to methyl −CH3. In tetracyanomethane C(−C≡N)4, four cyano groups are bonded to carbon. Although nitriles generally do not release cyanide ions, the cyanohydrins do and are thus toxic. The cyano group may be covalently bonded to atoms other than carbon, e.g., in cyanogen azide N3−C≡N, phosphorus tricyanide P(−C≡N)3 and trimethylsilyl cyanide (CH3)3Si−C≡N.

Hydrogen cyanide, or H−C≡N, is a highly volatile toxic liquid that is produced on a large scale industrially. It is obtained by acidification of cyanide salts.

The cyanide ion C≡N is isoelectronic with carbon monoxide C≡O+ and with molecular nitrogen N≡N. A triple bond exists between C and N. The negative charge is concentrated on carbon C.

Cyanides are produced by certain insects, bacteria, fungi, and algae. It is an antifeedant in a number of plants. Cyanides are found in substantial amounts in certain seeds and fruit stones, e.g., those of bitter almonds, apricots, apples, and peaches. Chemical compounds that can release cyanide are known as cyanogenic compounds. In plants, cyanides are usually bound to sugar molecules in the form of cyanogenic glycosides and defend the plant against herbivores. Cassava roots (also called manioc), an important potato-like food grown in tropical countries (and the base from which tapioca is made), also contain cyanogenic glycosides.

The Madagascar bamboo Cathariostachys madagascariensis produces cyanide as a deterrent to grazing. In response, the golden bamboo lemur, which eats the bamboo, has developed a high tolerance to cyanide.

The hydrogenase enzymes contain cyanide ligands attached to iron in their active sites. The biosynthesis of cyanide in the NiFe hydrogenases proceeds from carbamoyl phosphate, which converts to cysteinyl thiocyanate, the CN donor.

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