Jump to content

Nitrosyl cyanide

From Wikipedia, the free encyclopedia
The printable version is no longer supported and may have rendering errors. Please update your browser bookmarks and please use the default browser print function instead.
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[1]
CN2O
Molar mass 56.024 g·mol−1
Appearance blue-green gas
Boiling point −40 °C (−40 °F; 233 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

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. ^ a b c d Kirby, G. W. (1977). "Electrophilic C-nitroso-compounds". Chemical Society Reviews. 6: 5–11. doi:10.1039/CS9770600001 (Tilden lecture).
  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.