Cyanogen
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{{Chembox new
| Name = '''Cyanogen'''
| ImageFile = Cyanogen-2D-dimensions.png
| ImageSize = 200px
| ImageName = Cyanogen
| ImageFile1 = Cyanogen-3D-vdW.png
| ImageSize1 = 200px
| IUPACName = Ethanedinitrile
| OtherNames = Cyanogen<br />Carbon nitride<br />Dicyan<br />Dicyanogen<br />Nitriloacetonitrile<br />Oxalic acid dinitrile<br />Oxalonitrile<br />Oxalyl cyanide
| Section1 = {{Chembox Identifiers
| CASNo = 460-19-5
| SMILES = N#CC#N
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>2</sub>N<sub>2</sub>
| MolarMass = 52.04 g mol<sup>−1</sup>
| Density = 0.95 g cm<sup>−3</sup> at −21 °C
| MeltingPt = {{{melting point|−28}}} °C
| BoilingPt = {{{boiling point|−21}}} °C
}}
| Section7 = {{Chembox Hazards
| NFPA-H = 4
| NFPA-F = 4
| NFPA-R = 2
}}
}}
'''Cyanogen''' is the [[chemical compound]] with the [[chemical formula|formula]] ([[carbon|C]][[nitrogen|N]])<sub>2</sub>. It is a [[colorless]], toxic [[gas]] with a [[pungency|pungent]] [[odor]].
The molecule is a [[pseudohalogen]]. Cyanogen molecules consist of two CN groups (analogous to diatomic halogen molecules, such as [[chlorine|Cl]]<sub>2</sub> but is far less oxidizing). The two [[cyanide|cyano]] groups are bonded together at their [[carbon]] atoms: N≡C−C≡N, although other isomers have been detected. Certain derivatives of cyanogen are also called “cyanogen” even though they contain only one CN group. For example [[Cyanogen bromide]] is the compound with the structure NCBr.<ref>Hartman W. W.; Dreger, E. E.
"Cyanogen Bromide" Organic Syntheses, Collected Volume 2, p.150 (1943).http://www.orgsyn.org/orgsyn/pdfs/CV2P0150.pdf</ref>
Cyanogen is the [[anhydride]] of [[oxamide]]:
:H<sub>2</sub>NC(O)C(O)NH<sub>2</sub> → NCCN + 2 H<sub>2</sub>O
==Preparation==
Cyanogen is typically generated from cyanide compounds. One laboratory method entails thermal decomposition of [[mercury(II) cyanide|mercuric cyanide]]:
:2 Hg(CN)<sub>2</sub> → (CN)<sub>2</sub> + 2 HgCN
Alternatively, one can combine solutions of copper(II) salts (such as [[copper(II) sulfate]]) with cyanides, an unstable copper(II) cyanide is formed which rapidly decomposes into [[copper(I) cyanide]] and cyanogen.<ref>{{cite journal
| title = The Synthesis And Chemistry Of Cyanogen
| author = T. K. Brotherton, J. W. Lynn
| journal = [[Chemical Reviews]]
| volume = 59
| issue = 5
| pages = 841–883
| year = 1959
| doi = 10.1021/cr50029a003}}
</ref>
:2 CuSO<sub>4</sub> + 4 KCN → (CN)<sub>2</sub> + 2 CuCN + 2 K<sub>2</sub>SO<sub>4</sub>
Industrially, it is made by the oxidation of [[hydrogen cyanide]], usually using [[chlorine]] over an activated [[silicon dioxide]] [[catalyst]] or [[nitrogen dioxide]] over a [[copper]] salt. It is also formed when [[nitrogen]] (N<sub>2</sub>) and [[acetylene]] (C<sub>2</sub>[[Hydrogen|H]]<sub>2</sub>) are made to react by an electrical spark or discharge.<ref>{{cite journal
| title = Showing the Progress and Development of Processes for the the manufacture of Cyanogen and its Derivates (in: THE FIXATION OF ATMOSPHERIC NITROGEN
| author = A. A. Breneman
| journal = [[Journal of the American Chemical Society]]
| volume = 11
| issue = 1
| pages = 2–28
| year = 1959
| doi = 10.1021/ja02126a001}}</ref>
==History==
Cyanogen has a long history and was probably first generated by [[Carl Scheele]] around 1782 in the course of his studies of [[hydrogen cyanide]].<ref>{{cite journal
| title = Die ersten organisch-chemischen Synthesen
| author = H. Bauer
| journal = Naturwissenschaften
| volume = 67
| issue = 1
| pages = 1–6
| year = 1980
| doi = 10.1007/BF00424496}}
</ref>
<ref>{{cite journal
| title = ?
| author = [[Gay-Lussac|J. Gay-Lussac]]
| journal = Ann. chim. et phys.
| volume = 96
| pages = 175
| year = 1815}}
</ref>The first confirmed synthesis was reported 1802, when it was used to make what we now know as [[cyanogen chloride]]. It attained importance with the growth of the [[fertilizer]] industry in the late nineteenth century and is still an important intermediate in the production of many fertilizers. It is also used as a stabilizer in the production of [[nitrocellulose]].
==Safety==
Like other inorganic [[cyanide]]s, cyanogen is very toxic, as it undergoes reduction to [[cyanide]], which binds more strongly than oxygen to the [[cytochrome c oxidase]] complex, thus interrupting the [[mitochondrion|mitochondrial]] [[electron transfer chain]]. Cyanogen gas is an irritant to the eyes and respiratory system. Inhalation can lead to headache, dizziness, rapid pulse, nausea, vomiting, loss of consciousness, convulsions and death, depending on exposure.<ref name="HitCL">Muir, GD (ed.) 1971, ''Hazards in the Chemical Laboratory'', The Royal Institute of Chemistry, London.</ref>
Cyanogen produces the second hottest known natural flame (after [[Carbon subnitride]]) with a temperature of over 4525°C (8180°F) when it burns in oxygen.<ref>{{Citation
| last = Thomas
| first =N.
| author-link =
| last2 =Gaydon, A. G.; Brewer, L.
| first2 =
| author2-link =
| title = Cyanogen Flames and the Dissociation Energy of N2
| journal =The Journal of Chemical Physics
| volume =20
| issue =3
| pages =369–374
| date =March 1952
| year =
| url =http://scitation.aip.org/getabs/servlet/GetabsServlet?prog=normal&id=JCPSA6000020000003000369000001&idtype=cvips&gifs=yes
| doi =
| id = }}</ref>
==See also==
*[[Pseudohalogen]]
==References==
<references/>
==External links==
{{commonscat|cyanogen}}
* [http://www.npi.gov.au/database/substance-info/profiles/29.html National Pollutant Inventory - Cyanide compounds fact sheet]
[[Category:Cyanides]]
[[Category:Nitrogen compounds]]
[[Category:Inorganic carbon compounds]]
[[Category:Nitriles]]
[[bn:সায়ানোজেন]]
[[ca:Cianogen (pseudohalogen)]]
[[cs:Dikyan]]
[[de:Cyan (Chemie)]]
[[et:Tsüaan]]
[[es:Cianógeno]]
[[fr:Cyanogène]]
[[it:Cianogeno]]
[[ja:ジシアン]]
[[pl:Cyjan (związek chemiczny)]]
[[ru:Циан (химия)]]
[[vi:Xyanogen]]
[[zh:氰]]