Nitrosyl cyanide

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

Nitrosyl cyanide
Identifiers
3D model (JSmol)
ChemSpider
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

In terms of its structure, 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 generated 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]

  • Nitryl cyanide (O2NCN), a colorless gas (b.p. 7 °C).[3]

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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