Editing Cyanide (section)

{{short description|Any molecule with a cyano group (C≡N)}}
{{About|the class of chemical compounds}}
{{distinguish|Nitrile}}
{{Chembox
| ImageFile = Cyanide-montage.png
| ImageAlt = Space-filling model of the cyanide anion: carbon bound to smaller nitrogen atom
| Name=
| PIN = 
| SystematicName = Nitridocarbonate(II)
| IUPACName =
| OtherNames =
|Section1 = {{Chembox Identifiers
| CASNo = 57-12-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = OXN4E7L11K
| PubChem = 5975
| ChEBI = 17514
| SMILES = [C-]#N
| ChemSpiderID = 5755
| InChI = 1S/CN/c1-2/q-1
| InChIKey = XFXPMWWXUTWYJX-UHFFFAOYSA-N
}}
|Section2 = {{Chembox Properties
| Formula = {{chem2|CN−}}
| C=1|N=1
| Appearance =
| Solubility =
| ConjugateAcid = [[Hydrogen cyanide]]}}
|Section3 = {{Chembox Hazards
| MainHazards = The cyanide ion {{chem2|CN−}} is one of the most poisonous chemicals. It may cause death in minutes.
| FlashPt =
| AutoignitionPt = }}
}}

In [[chemistry]], '''cyanide''' ({{ety|el|kyanos|[[Prussian blue|dark blue]]}}) is an [[inorganic]] [[chemical compound]] that contains a {{chem2|C\tN|auto=1}} [[functional group]]. This group, known as the '''cyano group''', consists of a [[carbon]] atom [[triple-bond]]ed to a [[nitrogen]] atom.<ref>{{cite journal|url=http://goldbook.iupac.org/C01486.html |title=cyanides|website=[[IUPAC Gold Book]] |date=2014 |doi=10.1351/goldbook.C01486 |doi-access=free}}</ref>

[[Salt (chemistry)|Ionic]] cyanides contain the cyanide [[anion]] {{chem2|−C\tN}}. This anion is [[Cyanide poisoning|extremely poisonous]]. Soluble cyanide [[Salt (chemistry)|salts]] such as [[sodium cyanide]] (NaCN), [[potassium cyanide]] (KCN) and [[tetraethylammonium cyanide]] ({{chem2|[(CH3CH2)4N]CN}}) are highly toxic.<ref name="CMC">{{Cite web| url=http://www.cyanidecode.org/cyanide_environmental.php| title=Environmental and Health Effects of Cyanide| publisher=International Cyanide Management Institute| year=2006| access-date=4 August 2009| archive-date=30 November 2012| archive-url=https://web.archive.org/web/20121130094124/http://www.cyanidecode.org/cyanide_environmental.php| url-status=dead}}</ref>

[[Covalent]] cyanides contain the {{chem2|\sC\tN}} group, and are usually called [[nitrile]]s if the group is linked by a [[Single bond|single]] [[covalent bond]] to [[carbon]] atom. For example, in [[acetonitrile]] {{chem2|CH3\sC\tN}}, the cyanide group is bonded to [[methyl]] {{chem2|\sCH3}}. In [[tetracyanomethane]] {{chem2|C(\sC\tN)4}}, four cyano groups are bonded to carbon. Although nitriles generally do not release cyanide ions, the [[cyanohydrin]]s do and are thus toxic. The cyano group may be covalently bonded to atoms different than carbon, e.g., in [[cyanogen azide]] {{chem2|N3\sC\tN}}, [[phosphorus tricyanide]] {{chem2|P(\sC\tN)3}} and [[trimethylsilyl cyanide]] {{chem2|(CH3)3Si\sC\tN}}.

[[Hydrogen cyanide]], or {{chem2|H\sC\tN}}, is a highly [[Volatility (chemistry)|volatile]] toxic liquid that is produced on a large scale industrially. It is obtained by [[Acid|acidification]] of cyanide salts.