Cyanogen 377228 220608535 2008-06-20T18:07:05Z DOI bot 6652755 Citation maintenance. You can [[WP:DOI|use this bot]] yourself! Please [[User:DOI_bot/bugs|report any bugs]]. {{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]]