Formyl cyanide

Formyl cyanide is a simple organic molecule with formula HCOCN. It is simultaneously a nitrile and a carbonyl. Formyl cyanide is the simplest member of the acyl cyanide family. It is known to occur in space in the Sgr B2 molecular cloud.[1]

Formyl cyanide
Names
Systematic IUPAC name
Methanoyl cyanide
Other names
Cyanoformaldehyde
Glyoxylonitrile
2-oxo-acetonitrile
oxo-acetonitrile
Identifiers
3D model (JSmol)
ChemSpider
Properties
C2HNO
Molar mass 55.036 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Production

Formyl cyanide was first made by heating methoxyacetonitrile at 600 °C. Formyl cyanide can also be made by heating cinnamyloxyacetonitrile[2] or allyloxyacetonitrile.[3][4]

In molecular clouds, formation of formyl cyanide is speculated to result from formaldehyde and the cyanide radical:[5]

CH2O + CN• → HCOCN + H•

In Earth's atmosphere, the pollutant acrylonitrile reacts with hydroxyl radical forming formyl cyanide, hydroperoxyl and formaldehyde:[6]

CH2=CHCN + OH• + 1.5 O2 → HO2 + HCOCN + CH2O

Reactions

Formyl cyanide reacts with water to form formic acid and hydrogen cyanide.[2]

By formally substituting the hydrogen atom, cyanoformyl chloride, ClC(O)CN, and cyanoformyl bromide, BrC(O)CN are obtained.[7]

References
  1. Gronowski, Marcin; Eluszkiewicz, Piotr; Custer, Thomas Gage (12 April 2017). "Structure and Spectroscopy of C2HNO Isomers". The Journal of Physical Chemistry A. 121 (17): 3263. Bibcode:2017JPCA..121.3263G. doi:10.1021/acs.jpca.6b12609. PMID 28402122.
  2. Lewis-Bevan, Wyn; Gaston, Rick D.; Tyrrell, James; Stork, Wilmer D.; Salmon, Gary L. (March 1992). "Formyl cyanide: a stable species. Experimental and theoretical studies". Journal of the American Chemical Society. 114 (6): 1933–1938. doi:10.1021/ja00032a001.
  3. Bogey, M.; Destombes, J.L.; Vallee, Y.; Ripoll, J.L. (May 1988). "Formyl cyanide: Efficient production from allyloxyacetonitrile and its millimeter-wave spectrum". Chemical Physics Letters. 146 (3–4): 227–229. Bibcode:1988CPL...146..227B. doi:10.1016/0009-2614(88)87435-9.
  4. Bogey, M.; Demuynck, C.; Destombes, J.L.; Vallee, Y. (August 1995). "Millimeter-Wave Spectrum of Formyl Cyanide, HCOCN: Centrifugal Distortion and Hyperfine Structure Analysis". Journal of Molecular Spectroscopy. 172 (2): 344–351. Bibcode:1995JMoSp.172..344B. doi:10.1006/jmsp.1995.1183.
  5. Remijan, Anthony J.; Hollis, J. M.; Lovas, F. J.; Stork, Wilmer D.; Jewell, P. R.; Meier, D. S. (10 March 2008). "Detection of Interstellar Cyanoformaldehyde (CNCHO)". The Astrophysical Journal. 675 (2): L85–L88. Bibcode:2008ApJ...675L..85R. doi:10.1086/533529.
  6. Grosjean, Daniel (December 1990). "Atmospheric Chemistry of Toxic Contaminants. 3. Unsaturated Aliphatics: Acrolein, Acrylonitrile, Maleic Anhydride". Journal of the Air & Waste Management Association. 40 (12): 1664–1669. doi:10.1080/10473289.1990.10466814.
  7. Pasinszki, Tibor; Vass, Gábor; Klapstein, Dieter; Westwood, Nicholas P. C. (5 April 2012). "Generation, Spectroscopy, and Structure of Cyanoformyl Chloride and Cyanoformyl Bromide, XC(O)CN". The Journal of Physical Chemistry A. 116 (13): 3396–3403. Bibcode:2012JPCA..116.3396P. doi:10.1021/jp301528q.
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