For the Android distribution, see CyanogenMod.
Cyanogen
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| Names |
IUPAC name
- Ethanedinitrile[3] (substitutive)
- Bis(nitridocarbon)(C—C)[3] (additive)
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Other names
- Dicyan[1][2]
- Carbon nitride[1]
- Oxalic acid dinitrile[2]
- Dicyanogen
- Nitriloacetonitrile
- Oxalonitrile[1]
- Oxalyl cyanide
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| Identifiers |
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CAS Number
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460-19-5 Y |
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Beilstein Reference
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1732464 |
| ChEBI |
CHEBI:29308 Y |
| ChemSpider |
9605 Y |
| EC Number |
207-306-5 |
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Gmelin Reference
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1090 |
| Jmol interactive 3D |
Image |
| MeSH |
cyanogen |
| PubChem |
9999 |
| RTECS number |
GT1925000 |
| UN number |
1026 |
InChI
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InChI=1S/C2N2/c3-1-2-4 Y
Key: JMANVNJQNLATNU-UHFFFAOYSA-N Y
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| Properties |
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Chemical formula
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(CN)2 |
| Appearance |
Colourless gas |
| Odor |
pungent, almond-like |
| Density |
950 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 |
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Solubility in water
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45 g/100 mL (at 20 °C) |
| Solubility |
soluble in ethanol, ethyl ether |
| Vapor pressure |
5.1 atm (21 °C)[4] |
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Henry's law
constant (kH)
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1.9 μmol Pa−1 kg−1 |
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Refractive index (nD)
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1.327 (18 °C) |
| Thermochemistry |
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Std molar
entropy (So298)
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241.57 J K−1 mol−1 |
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Std enthalpy of
formation (ΔfHo298)
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309.07 kJ mol−1 |
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Std enthalpy of
combustion (ΔcHo298)
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−1.0978–−1.0942 MJ mol−1 |
| Hazards |
| Main hazards |
forms cyanide in the body; flammable[4] |
| Safety data sheet |
inchem.org |
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EU classification (DSD)
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F+ T N |
| R-phrases |
R12, R23, R50/53 |
| S-phrases |
(S1/2), S16, S33, S45, S63 |
| NFPA 704 |
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| Explosive limits |
6.6–32%[4] |
| US health exposure limits (NIOSH): |
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PEL (Permissible)
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none[4] |
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REL (Recommended)
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TWA 10 ppm (20 mg/m3)[4] |
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IDLH (Immediate danger
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N.D.[4] |
| Related compounds |
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Related alkanenitriles
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- Hydrogen cyanide
- Thiocyanic acid
- Cyanogen iodide
- Cyanogen bromide
- Cyanogen chloride
- Cyanogen fluoride
- Acetonitrile
- Aminoacetonitrile
- Glycolonitrile
- Propanenitrile
- Aminopropionitrile
- Malononitrile
- Pivalonitrile
- Acetone cyanohydrin
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Related compounds
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DBNPA |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Y verify (what is YN ?) |
| Infobox references |
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Cyanogen is the chemical compound with the formula (CN)2. It is a colorless, toxic gas with a pungent odor. The molecule is a pseudohalogen. Cyanogen molecules consist of two CN groups – analogous to diatomic halogen molecules, such as Cl2, but far less oxidizing. The two cyano groups are bonded together at their carbon atoms: N≡C−C≡N, although other isomers have been detected.[5] Certain derivatives of cyanogen are also called "cyanogen" even though they contain only one CN group. For example cyanogen bromide has the formula NCBr.[6]
Cyanogen is the anhydride of oxamide:
- H2NC(O)C(O)NH2 → NCCN + 2 H2O
although oxamide is manufactured from cyanogen by hydrolysis:[7]
- NCCN + 2 H2O → H2NC(O)C(O)NH2
Contents
- 1 Preparation
- 2 Paracyanogen
- 3 History
- 4 Safety
- 5 See also
- 6 References
- 7 External links
Preparation
Cyanogen is typically generated from cyanide compounds. One laboratory method entails thermal decomposition of mercuric cyanide:
- 2 Hg(CN)2 → (CN)2 + Hg2(CN)2
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.[8]
- 2 CuSO4 + 4 KCN → (CN)2 + 2 CuCN + 2 K2SO4
Industrially, it is created 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 and acetylene are reacted by an electrical spark or discharge.[9]
Paracyanogen
Paracyanogen can be best prepared by heating mercuric cyanide. It can also be prepared by heating silver cyanide, silver cyanate, cyanogen iodide or cyanuric iodide.[10] It can also be prepared by the polymerization of cyanogen at 300-500 °C in the presence of trace impurities. Paracyanogen can also be converted back to cyanogen by heating to 800 °C.[7] Based on experimental evidence, the structure of this polymeric material is thought to be rather irregular, with most of the carbon atoms being of sp2 type and localized domains of pi conjugation.[11]
History
Cyanogen was first synthesized in 1815 by Joseph 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, I create), because cyanide was first isolated by the Swedish chemist Carl Wilhelm Scheele from the pigment "Prussian blue".[12] By the 1850s, cyanogen soap was used by photographers to remove silver stains from their hands. [13] 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.
Cyanogen is a highly toxic compound, and in 1910 a spectroscopic analysis of Halley's Comet found cyanogen in the comet's tail. This led to public fear that the Earth would be poisoned as it passed through the tail. Because of the extremely diffuse nature of the tail, there was no effect when the planet passed through it.[14][15]
Safety
Like other inorganic cyanides, cyanogen is very toxic, as it readily undergoes reduction to cyanide, which poisons the cytochrome c oxidase complex, thus interrupting the 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.[16] Lethal dose through inhalation typically ranges from 100 to 150 mg. Inhalation of 900 ppm over a period of 10 min is considered lethal.[17]
Cyanogen produces the second hottest known natural flame (after carbon subnitride) with a temperature of over 4525 °C (or 8177 °F) when it burns in oxygen.[18][19]
See also
References
- ^ a b c NIOSH 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.
- ^ a b The Merck Index (10th ed.). Rahway, NJ: Merck & Co. 1983. p. 385.
- ^ a b "oxalonitrile (CHEBI:29308)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 27 October 2006. Main. Retrieved 6 June 2012.
- ^ a b c d e f "NIOSH Pocket Guide to Chemical Hazards #0161". National Institute for Occupational Safety and Health (NIOSH).
- ^ 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.
- ^ Hartman, W. W.; Dreger, E. E. (1931). "Cyanogen Bromide" (PDF). Org. Synth. 11: 30. ; Coll. Vol. 2, p. 150
- ^ a b Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. pp. 320–321. ISBN 0-08-037941-9.
- ^ Brotherton, T. K.; Lynn, J. W. (1959). "The Synthesis And Chemistry Of Cyanogen". Chemical Reviews 59 (5): 841–883. doi:10.1021/cr50029a003.
- ^ Breneman, A. A. (1889). "The Fixation of Atmospheric Nitrogen". Journal of the American Chemical Society 11 (1): 2–27. doi:10.1021/ja02126a001.
- ^ 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.
- ^ Maya, Leon (1993). "Paracyanogen Reexamined". Polymer Science: Part A 31: 2595–2600.
- ^ Gay-Lussac, J. L. (1815). "Recherches sur l'acide prussique". Annales de Chimie 95: 136–231. Gay-Lussac names cyanogen on p. 163.
- ^ Crookes, William, ed. (1859). "Photographic News: A Weekly Record of the Process of the Photography": 11–11.
- ^ Comet's Poisonous Tail
- ^ Halley's Comet 100 years Ago
- ^ Muir, G. D., ed. (1971). Hazards in the Chemical Laboratory. London: The Royal Institute of Chemistry.
- ^ Ledgard, Jared (2006). A Laboratory History of Chemical Warfare Agents. Lulu.com. ISBN 0615136451. p. 82.
- ^ 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.
- ^ 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.
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Nitrogen compounds
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Chemical formulas
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External links
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Wikimedia Commons has media related to cyanogen. |
- National Pollutant Inventory - Cyanide compounds fact sheet
- PhysOrg.com
- CDC - NIOSH Pocket Guide to Chemical Hazards
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Molecules detected in outer space
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| Molecules |
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Deuterated
molecules |
- Ammonia
- Ammonium ion
- Formaldehyde
- Formyl radical
- Heavy water
- Hydrogen cyanide
- Hydrogen deuteride
- Hydrogen isocyanide
- Methylacetylene
- N2D+
- Trihydrogen cation
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| Unconfirmed |
- Anthracene
- Dihydroxyacetone
- Ethyl methyl ether
- Glycine
- Graphene
- H2NCO+
- Linear C5
- Naphthalene cation
- Phosphine
- Pyrene
- Silylidine
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| Related |
- Abiogenesis
- Astrobiology
- Astrochemistry
- Atomic and molecular astrophysics
- Chemical formula
- Circumstellar envelope
- Cosmic dust
- Cosmic ray
- Cosmochemistry
- Diffuse interstellar band
- Extraterrestrial life
- Extraterrestrial liquid water
- Forbidden mechanism
- Helium hydride ion
- Homochirality
- Intergalactic dust
- Interplanetary medium
- Interstellar medium
- Iron–sulfur world theory
- Kerogen
- Life
- Molecules in stars
- Nexus for Exoplanet System Science
- Organic compound
- Outer space
- PAH world hypothesis
- Panspermia
- Polycyclic aromatic hydrocarbon (PAH)
- RNA world hypothesis
- Spectroscopy
- Tholin
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- Book:Chemistry
- Category:Astrochemistry
- Category:Molecules
- Portal:Astrobiology
- Portal:Chemistry
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