Nitrosyl Cyanide
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Nitrosyl cyanide, a blue-green gas, is the compound with the
molecular formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...
ONCN. The compound has been invoked as a product of the oxidation of
cyanamide Cyanamide is an organic compound with the chemical formula, formula carbon, Cnitrogen, N2hydrogen, H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcoho ...
catalyzed by the enzyme
glucose oxidase The glucose oxidase enzyme (GOx or GOD) also known as notatin (EC number 1.1.3.4) is an oxidoreductase that catalyses the oxidation of glucose to hydrogen peroxide and D-glucono-δ-lactone. This enzyme is produced by certain species of fungi and ...
.


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 Nitrosyl chloride is the chemical compound with the formula NOCl. It is a yellow gas that is commonly encountered as a component of aqua regia, a mixture of 3 parts concentrated hydrochloric acid and 1 part of concentrated nitric acid. It is a st ...
. 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 1,3-Butadiene () is the organic compound with the formula (CH2=CH)2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two viny ...
. Cycloadditions occur across the N=O bond. It forms a reversible adduct with 9,10-dimethylantracene.


Related compound

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Nitryl cyanide Nitryl cyanide is an energetic chemical compound with the formula NCNO2. Nitryl cyanide is a possible precursor to 2,4,6-trinitro-1,3,5-triazine. Synthesis Nitryl cyanide was first synthesized in 2014. The reaction of nitronium tetrafluorobor ...
(O2NCN), a colorless gas (b.p. 7 °C).{{cite journal , doi=10.1002/anie.201404209, title=Nitryl Cyanide, NCNO2, year=2014, last1=Rahm, first1=Martin, last2=Bélanger-Chabot, first2=Guillaume, last3=Haiges, first3=Ralf, last4=Christe, first4=Karl O., journal=Angewandte Chemie International Edition, volume=53, issue=27, pages=6893–6897, pmid=24861214


References

Cyanide Cyanide is a naturally occurring, rapidly acting, toxic chemical that can exist in many different forms. In chemistry, a cyanide () is a chemical compound that contains a functional group. This group, known as the cyano group, consists of ...
Nitrogen(III) compounds Gases with color