Nitrosyl cyanide explained

Nitrosyl cyanide, a blue-green gas, 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.[1]

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°.

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.

Related compound

References

  1. 10.1016/0006-2952(96)00174-8. Nitrosyl cyanide, a putative metabolic oxidation product of the alcohol-deterrent agent cyanamide. 1996. Shirota. Frances N.. Goon. David J.W.. Demaster. Eugene G.. Nagasawa. Herbert T.. Biochemical Pharmacology. 52. 1. 141–147. 8678898.
  2. 10.1002/anie.201404209. Nitryl Cyanide, NCNO2. 2014. Rahm. Martin. Bélanger-Chabot. Guillaume. Haiges. Ralf. Christe. Karl O.. Angewandte Chemie International Edition. 53. 27. 6893–6897. 24861214.

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