Editing Cyanogen (section)

{{Short description|Chemical compound (CN)₂, functional group -CN-, or radical CN·}}
{{Distinguish|cyanamide|hydrogen cyanide|Cyanide}}
{{for|the Android distribution|CyanogenMod}}
{{Chembox
| Watchedfields = changed
| verifiedrevid = 444495670
| ImageFile = File:Cyanogen 200.svg
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 100
| ImageName = Skeletal formula of cyanogen
| ImageFileL1 = Cyanogen-3D-balls.png
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageNameL1 = Ball and stick model of cyanogen
| ImageFileR1 = Cyanogen-3D-vdW.png
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageNameR1 = Spacefill model of cyanogen
| PIN = Oxalonitrile<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 902 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter}}</ref>
| SystematicName = Ethanedinitrile<ref name=iupac2013 />
| OtherNames = {{ubl|Cyanogen|Bis(nitridocarbon)(''C''—''C'')<ref name=ChEBI>{{Cite web|title=oxalonitrile (CHEBI:29308)| url=https://www.ebi.ac.uk/chebi/searchId.do?chebiId=29308|work=Chemical Entities of Biological Interest|publisher=European Bioinformatics Institute|access-date=6 June 2012|location=UK|date=27 October 2006|at=Main}}</ref>|Dicyan<ref Name="Pocket">{{cite book |title=NIOSH Pocket Guide to Chemical Hazards|date=September 2007 |publisher=Department of Health and Human Services, Centers for Disease Control, National Institute for Occupational Safety & Health |page=82}}</ref><ref name = "Merck">{{cite book |title=The Merck Index|url=https://archive.org/details/merckindexencycl00wind|url-access=registration|edition=10th|year=1983|publisher=Merck & Co. |location=Rahway, NJ|page=[https://archive.org/details/merckindexencycl00wind/page/385 385]|isbn=9780911910278}}</ref>|Carbon nitride<ref Name="Pocket" />|Oxalic acid dinitrile<ref name="Merck" />|Dicyanogen|Nitriloacetonitrile|CY}}
|Section1={{Chembox Identifiers
| CASNo = 460-19-5
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 534Q0F66RK
| PubChem = 9999
| ChemSpiderID = 9605
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 207-306-5
| UNNumber = 1026
| MeSHName = cyanogen
| ChEBI = 29308
| ChEBI_Ref = {{ebicite|correct|EBI}}
| RTECS = GT1925000
| Beilstein = 1732464
| Gmelin = 1090
| SMILES = N#CC#N
| StdInChI = 1S/C2N2/c3-1-2-4
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JMANVNJQNLATNU-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
| Formula = {{chem2|N\tC\sC\tN}}
| C=2 | N=2
| Appearance = Colourless gas
| Odor = pungent, [[Almond#Sweet and bitter almonds|bitter almond]]-like
| Density = 950 mg/mL (at −21&nbsp;°C)
| MeltingPtC = -28
| BoilingPtK = 252.0
| Solubility = 45 g/100 mL (at 20&nbsp;°C)
| SolubleOther = soluble in [[ethanol]], [[ethyl ether]]
| HenryConstant = 1.9 μmol/(Pa·kg)
| RefractIndex = 1.327 (18&nbsp;°C)
| VaporPressure = 5.1 atm (21&nbsp;°C)<ref name=PGCH/>
| MagSus = −21.6·10<sup>−6</sup> cm<sup>3</sup>/mol
}}
|Section3={{Chembox Thermochemistry
| DeltaHf = 309.07 kJ/mol
| DeltaHc = −1.0978–−1.0942 MJ/mol
| Entropy = 241.57 J/(K·mol)
}}
|Section4={{Chembox Hazards
| ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics1390.htm inchem.org]
| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|220|331|410}}
| PPhrases = {{P-phrases|210|261|271|273|304+340|311|321|377|381|391|403|403+233|405|501}}
| NFPA-H = 4
| NFPA-F = 4
| NFPA-R = 2
| ExploLimits = 6.6–32%<ref name=PGCH/>
| PEL = none<ref name=PGCH>{{PGCH|0161}}</ref>
| IDLH = N.D.<ref name=PGCH/>
| REL = TWA 10 ppm (20 mg/m<sup>3</sup>)<ref name=PGCH/>
| MainHazards = forms [[cyanide]] in the body; flammable<ref name=PGCH/> 
}}
|Section5={{Chembox Related
| OtherFunction_label = alkanenitriles
| OtherFunction = {{ubl|[[Hydrogen cyanide]]|[[Thiocyanic acid]]|[[Cyanogen iodide]]|[[Cyanogen bromide]]|[[Cyanogen chloride]]|[[Cyanogen fluoride]]|[[Cyanogen azide]]|[[Acetonitrile]]|[[Aminoacetonitrile]]|[[Glycolonitrile]]|[[Propionitrile]]|[[Aminopropionitrile]]|[[Malononitrile]]|[[Pivalonitrile]]|[[Acetone cyanohydrin]]}}
| OtherCompounds = [[DBNPA]]
}}
}}
'''Cyanogen''' is the [[chemical compound]] with the [[chemical formula|formula]] {{chem2|(CN)2|auto=1}}. Its structure is {{chem2|N\tC\sC\tN}}. The simplest stable [[carbon nitride]], it is a [[Transparency and translucency|colorless]] and highly [[toxic]] [[gas]] with a [[pungency|pungent]] [[odor]]. The molecule is a [[pseudohalogen]]. Cyanogen molecules are [[linear molecular geometry|linear]], and consist of two CN groups ‒ analogous to diatomic halogen molecules, such as [[chlorine|Cl]]{{sub|2}}, but far less oxidizing. The two [[cyanide|cyano groups]] are bonded together at their [[carbon]] atoms, though other [[isomer]]s have been detected.<ref>{{cite journal |author1=Ringer, A. L. |author2=Sherrill, C. D. |author3=King, R. A. |author4=Crawford, T. D. | year = 2008 | title = Low-lying singlet excited states of isocyanogen | journal = International Journal of Quantum Chemistry | volume = 106 | issue = 6 | pages = 1137–1140 | doi = 10.1002/qua.21586 |bibcode = 2008IJQC..108.1137R}}</ref> The name is also used for the CN radical,<ref name=radical>{{cite book|doi=10.1007/978-3-642-11274-4_1806|chapter=Cyanogen Radical|title=Encyclopedia of Astrobiology|pages=402|year=2011|last1=Irvine|first1=William M.|isbn=978-3-642-11271-3}}</ref> and hence is used for compounds such as [[cyanogen bromide]] ({{chem2|Br\sC\tN}})<ref>{{OrgSynth |author=Hartman, W. W. |author2=Dreger, E. E. |title=Cyanogen Bromide |year=1931 |volume=11 |pages=30 |collvol=2 |collvolpages=150}}</ref> (but see also ''[[Cyano radical]]''). When burned at increased pressure with oxygen, it is possible to get a blue tinted flame, the temperature of which is about 4800°C (a higher temperature is possible with ozone). It is as such regarded as the gas with the second highest temperature of burning (after [[dicyanoacetylene]]).

Cyanogen is the [[anhydride]] of [[oxamide]]:
:{{chem2|H2N\sC(\dO)\sC(\dO)\sNH2 → N\tC\sC\tN + 2 H2O}}

though oxamide is manufactured from cyanogen by hydrolysis:<ref name=greenwood>{{Greenwood&Earnshaw2nd|pages=320–321}}</ref>

:{{chem2|N\tC\sC\tN + 2 H2O → H2N\sC(\dO)\sC(\dO)\sNH2}}