Nitrosyl cyanide

Nitrosyl cyanide, a blue-green gas,[1] is the compound with the molecular formula ONCN. The compound has been invoked as a product of the oxidation of cyanamide catalyzed by the enzyme glucose oxidase.[2]

Nitrosyl cyanide
Names
Preferred IUPAC name
Nitrous cyanide
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/CN2O/c2-1-3-4
    Key: CAMRHYBKQTWSCM-UHFFFAOYSA-N
  • C(#N)N=O
Properties
CN2O
Molar mass 56.024 g·mol−1
Appearance blue-green gas
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Structure, synthesis, reactivity

The structure of nitrosyl cyanide is planar. It is strongly bent at the internal nitrogen, analogous to the structure of nitrosyl chloride. The C-N-O angle is 113°. The NCN angle is 170°.[1]

The compound can be created by the reaction of nitrosyl chloride and silver cyanide at low temperatures. It is not typically isolated, but trapped by Diels-Alder reactions, e.g. with butadiene. Cycloadditions occur across the N=O bond. It forms a reversible adduct with 9,10-dimethylantracene.[1]

References
  1. Kirby, G. W. (1977). "Tilden Lecture. Electrophilic C-nitroso-compounds". Chemical Society Reviews. 6: 1. doi:10.1039/CS9770600001.
  2. Shirota, Frances N.; Goon, David J.W.; Demaster, Eugene G.; Nagasawa, Herbert T. (1996). "Nitrosyl cyanide, a putative metabolic oxidation product of the alcohol-deterrent agent cyanamide". Biochemical Pharmacology. 52 (1): 141–147. doi:10.1016/0006-2952(96)00174-8. PMID 8678898.
  3. Rahm, Martin; Bélanger-Chabot, Guillaume; Haiges, Ralf; Christe, Karl O. (2014). "Nitryl Cyanide, NCNO2". Angewandte Chemie International Edition. 53 (27): 6893–6897. doi:10.1002/anie.201404209. PMID 24861214.
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