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Cyanogen

From Wikipedia, the free encyclopedia
Chemical compound (CN)₂, functional group -CN-, or radical CN·
Not to be confused withcyanamide,hydrogen cyanide, orCyanide.
For the Android distribution, seeCyanogenMod.
Cyanogen
Skeletal formula of cyanogen
Skeletal formula of cyanogen
Ball and stick model of cyanogen
Ball and stick model of cyanogen
Spacefill model of cyanogen
Spacefill model of cyanogen
Names
Preferred IUPAC name
Oxalonitrile[4]
Systematic IUPAC name
Ethanedinitrile[4]
Other names
Cyanogen
Bis(nitridocarbon)(CC)[1]
Dicyan[2][3]
Carbon nitride[2]
Oxalic acid dinitrile[3]
Dicyanogen
Nitriloacetonitrile
CY
Identifiers
3D model (JSmol)
1732464
ChEBI
ChemSpider
ECHA InfoCard100.006.643Edit this at Wikidata
EC Number
  • 207-306-5
1090
MeSHcyanogen
RTECS number
  • GT1925000
UNII
UN number1026
  • InChI=1S/C2N2/c3-1-2-4 checkY
    Key: JMANVNJQNLATNU-UHFFFAOYSA-N checkY
  • N#CC#N
Properties
C2N2
Molar mass52.036 g·mol−1
AppearanceColourless gas
Odorpungent,bitter almond-like
Density950 mg mL−1 (at −21 °C)
Melting point−28 °C (−18 °F; 245 K)
Boiling point−21.1 °C; −6.1 °F; 252.0 K
45 g/100 mL (at 20 °C)
Solubilitysoluble inethanol,ethyl ether
Vapor pressure5.1 atm (21 °C)[5]
1.9 μmol Pa−1 kg−1
−21.6·10−6 cm3/mol
1.327 (18 °C)
Thermochemistry
241.57 J K−1 mol−1
309.07 kJ mol−1
−1.0978–−1.0942 MJ mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
formscyanide in the body; flammable[5]
GHS labelling:
GHS02: FlammableGHS06: ToxicGHS09: Environmental hazard
Danger
H220,H331,H410
P210,P261,P271,P273,P304+P340,P311,P321,P377,P381,P391,P403,P403+P233,P405,P501
NFPA 704 (fire diamond)
Explosive limits6.6–32%[5]
NIOSH (US health exposure limits):
PEL (Permissible)
none[5]
REL (Recommended)
TWA 10 ppm (20 mg/m3)[5]
IDLH (Immediate danger)
N.D.[5]
Safety data sheet (SDS)inchem.org
Related compounds
Related alkanenitriles
Related compounds
DBNPA
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Cyanogen is thechemical compound with theformula (CN)2. The simplest stablecarbon nitride, it is acolorless and highlytoxicgas with apungentodor. The molecule is apseudohalogen. Cyanogen molecules consist of two CN groups ‒ analogous to diatomic halogen molecules, such asCl2, but far less oxidizing. The twocyano groups are bonded together at theircarbon atoms: N≡C‒C≡N, though otherisomers have been detected.[6] The name is also used for the CN radical,[7] and hence is used for compounds such ascyanogen bromide (NCBr)[8] (but see alsoCyano 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 (afterdicyanoacetylene).

Cyanogen is theanhydride ofoxamide:

H2NC(O)C(O)NH2 → NCCN + 2 H2O

though oxamide is manufactured from cyanogen by hydrolysis:[9]

NCCN + 2 H2O → H2NC(O)C(O)NH2

Preparation

[edit]

Cyanogen is typically generated fromcyanide compounds. One laboratory method entails thermal decomposition ofmercuric cyanide:

2 Hg(CN)2 → (CN)2 + Hg2(CN)2

Or, one can combine solutions of copper(II) salts (such ascopper(II) sulfate) with cyanides; an unstable copper(II) cyanide is formed which rapidly decomposes intocopper(I) cyanide and cyanogen.[10]

2 CuSO4 + 4 KCN → (CN)2 + 2 CuCN + 2 K2SO4

Industrially, it is created by theoxidation ofhydrogen cyanide, usually usingchlorine over an activatedsilicon dioxidecatalyst ornitrogen dioxide over acopper salt. It is also formed whennitrogen andacetylene are reacted by an electrical spark or discharge.[11]

Reactions

[edit]

For the two less stable isomers of cyanogen, the order of the atoms differs. Isocyanogen (or cyanogen cyanide) is NCNC.[12] It has been detected in the interstellar medium]].[13]

Addition of sulfur monochloride to cyanogen gives3,4-dichloro-1,2,5-thiadiazole.

Paracyanogen

[edit]

Paracyanogen is apolymer of cyanogen. It can be best prepared by heatingmercury(II) cyanide. It can also be prepared by heatingsilver cyanide,silver cyanate,cyanogen iodide or cyanuric iodide.[14] It can also be prepared by the polymerization of cyanogen at 300 to 500 °C (572 to 932 °F) in the presence of trace impurities. Paracyanogen can also be converted back to cyanogen by heating to 800 °C (1,470 °F).[9] Based on experimental evidence, the structure of this polymeric material is thought to be rather irregular, with most of thecarbon atoms being ofsp2 type and localized domains ofπ conjugation.[15]

History

[edit]

Cyanogen was first synthesized in 1815 byJoseph Louis Gay-Lussac, who determined its empirical formula and named it. Gay-Lussac coined the word "cyanogène" from the Greek words κυανός (kyanos, blue) and γεννάω (gennao, to create), because cyanide was first isolated by Swedish chemistCarl Wilhelm Scheele from the pigmentPrussian blue.[16] It attained importance with the growth of thefertilizer industry in the late 19th century and remains an important intermediate in the production of many fertilizers. It is also used as a stabilizer in the production ofnitrocellulose.

Cyanogen is commonly found incomets.[17] In 1910 aspectroscopic analysis ofHalley's Comet found cyanogen in the comet's tail, which led to public fear that the Earth would be poisoned as it passed through the tail. People inNew York wore gas masks, and merchants soldquack "comet pills" claimed to neutralize poisoning.[17] Because of the extremely diffuse nature of the tail, there was no effect when the planet passed through it.[18][19]

Safety

[edit]

Like othercyanides, cyanogen is very toxic, as it readily undergoes reduction to cyanide, which poisons thecytochrome c oxidase complex, thus interrupting themitochondrialelectron 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.[20] Lethal dose through inhalation typically ranges from 100 to 150milligrams (1.5 to 2.3grains).

Cyanogen produces the second-hottest-known natural flame (afterdicyanoacetylene aka carbon subnitride) with a temperature of over 4,525 °C (8,177 °F) when it burns in oxygen.[21][22]

In popular culture

[edit]

In theDoctor Who serial "The Brain of Morbius" (the 5th serial of season 13), the Doctor synthesizes cyanogen using hydrogen cyanide as a starting material and vents it through a pipe to stop Solon from performing surgery on the brain of Morbius's body.

InDragnet (1987) Friday (Dan Aykroyd) and Streebek (Tom Hanks) are tracking down the villain who stole "the pseudohalogenic compound cyanogen".[23]

In the second season ofThe Night Agent, cyanogen is stolen from a chemical plant as part of a plot to manufacture achemical weapon.

See also

[edit]

References

[edit]
  1. ^"oxalonitrile (CHEBI:29308)".Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 27 October 2006. Main. Retrieved6 June 2012.
  2. ^abNIOSH Pocket Guide to Chemical Hazards. Department of Health and Human Services, Centers for Disease Control, National Institute for Occupational Safety & Health. September 2007. p. 82.
  3. ^abThe Merck Index (10th ed.). Rahway, NJ: Merck & Co. 1983. p. 385.ISBN 9780911910278.
  4. ^ab"Front Matter".Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge:Royal Society of Chemistry. 2014. p. 902.doi:10.1039/9781849733069-FP001.ISBN 978-0-85404-182-4.
  5. ^abcdefNIOSH Pocket Guide to Chemical Hazards."#0161".National Institute for Occupational Safety and Health (NIOSH).
  6. ^Ringer, A. L.; Sherrill, C. D.; King, R. A.; Crawford, T. D. (2008). "Low-lying singlet excited states of isocyanogen".International Journal of Quantum Chemistry.106 (6):1137–1140.Bibcode:2008IJQC..108.1137R.doi:10.1002/qua.21586.
  7. ^Irvine, William M. (2011). "Cyanogen Radical".Encyclopedia of Astrobiology. p. 402.doi:10.1007/978-3-642-11274-4_1806.ISBN 978-3-642-11271-3.
  8. ^Hartman, W. W.; Dreger, E. E. (1931). "Cyanogen Bromide".Organic Syntheses.11: 30;Collected Volumes, vol. 2, p. 150.
  9. ^abGreenwood, Norman N.; Earnshaw, Alan (1997).Chemistry of the Elements (2nd ed.).Butterworth-Heinemann. pp. 320–321.ISBN 978-0-08-037941-8.
  10. ^Brotherton, T. K.; Lynn, J. W. (1959). "The Synthesis And Chemistry Of Cyanogen".Chemical Reviews.59 (5):841–883.doi:10.1021/cr50029a003.
  11. ^Breneman, A. A. (January 1889)."The Fixation of Atmospheric Nitrogen".Journal of the American Chemical Society.11 (1):2–27.doi:10.1021/ja02126a001.
  12. ^Bickelhaupt, F. Matthias; Nibbering, Nico M. M.; Van Wezenbeek, Egbert M.; Baerends, Evert Jan (1992). "Central Bond in the Three CN.cntdot.dimers NC-CN, CN-CN and CN-NC: Electron Pair Bonding and Pauli Repulsion Effects".The Journal of Physical Chemistry.96 (12):4864–4873.doi:10.1021/j100191a027.
  13. ^Agúndez, M.; Marcelino, N.; Cernicharo, J. (2018)."Discovery of Interstellar Isocyanogen (CNCN): Further Evidence that Dicyanopolyynes Are Abundant in Space".The Astrophysical Journal Letters.861 (2): L22.arXiv:1806.10328.Bibcode:2018ApJ...861L..22A.doi:10.3847/2041-8213/aad089.PMC 6120679.PMID 30186588.
  14. ^Bircumshaw, L. L.; F. M. Tayler; D. H. Whiffen (1954). "Paracyanogen: its formation and properties. Part I".J. Chem. Soc.:931–935.doi:10.1039/JR9540000931.
  15. ^Maya, Leon (1993)."Paracyanogen Reexamined".Journal of Polymer Science Part A (Submitted manuscript).31 (10):2595–2600.Bibcode:1993JPoSA..31.2595M.doi:10.1002/pola.1993.080311020.
  16. ^Gay-Lussac, J. L. (1815)."Recherches sur l'acide prussique".Annales de Chimie (in French).95:136–231. Gay-Lussac names cyanogen on p. 163.
  17. ^ab"Cometary Poison Gas Geyser Heralds Surprises".science.nasa.gov. 2010-11-02. Archived fromthe original on 2010-11-06.
  18. ^"Comet's Poisonous Tail"(PDF).New York Times. 1910-02-08.
  19. ^"Halley's Comet 100 years ago".The Denver Post. 2010-05-25.
  20. ^Muir, G. D., ed. (1971).Hazards in the Chemical Laboratory. London: The Royal Institute of Chemistry.
  21. ^Thomas, N.; Gaydon, A. G.; Brewer, L. (1952). "Cyanogen Flames and the Dissociation Energy of N2".The Journal of Chemical Physics.20 (3):369–374.Bibcode:1952JChPh..20..369T.doi:10.1063/1.1700426.
  22. ^J. B. Conway; R. H. Wilson Jr.; A. V. Grosse (1953). "The Temperature of the Cyanogen-Oxygen Flame".Journal of the American Chemical Society.75 (2): 499.doi:10.1021/ja01098a517.
  23. ^"The trichlornitromethane and the pseudo-halogenic compound cyanogen". RetrievedAugust 18, 2021.

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