Nitrosyl cyanide

Nitrosyl cyanide
Names
Preferred IUPAC name
Nitrous cyanide
Identifiers
CAS Number
  • 4343-68-4
3D model (JSmol)
  • Interactive image
ChemSpider
  • 109829
PubChem CID
  • 123214
CompTox Dashboard (EPA)
  • DTXSID00195849
InChI
  • InChI=1S/CN2O/c2-1-3-4
    Key: CAMRHYBKQTWSCM-UHFFFAOYSA-N
  • C(#N)N=O
Properties[1]
Chemical formula
 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).
Infobox references
Chemical compound

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]

Related compound

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

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.
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Salts and covalent derivatives of the cyanide ion
HCN He
LiCN Be(CN)2 B(CN)3 C(CN)4
C2(CN)2 		NH4CN
ONCN
O2NCN
N3CN 		OCN−
-NCO
O(CN)2 		FCN Ne
NaCN Mg(CN)2 Al(CN)3 Si(CN)4
(CH3)3SiCN 		P(CN)3 SCN−
-NCS
(SCN)2
S(CN)2 		ClCN Ar
KCN Ca(CN)2 Sc(CN)3 Ti V Cr(CN)63− Mn Fe(CN)2
Fe(CN)64−
Fe(CN)63− 		Co(CN)2
Co(CN)3−
5 		Ni(CN)2
Ni(CN)42−
Ni(CN)44− 		CuCN Zn(CN)2 Ga(CN)3 Ge(CN)2
Ge(CN)4 		As(CN)3
(CH3)2AsCN
(C6H5)2AsCN 		SeCN−
(SeCN)2
Se(CN)2 		BrCN Kr
RbCN Sr(CN)2 Y(CN)3 Zr Nb Mo(CN)84− Tc Ru Rh Pd(CN)2 AgCN Cd(CN)2 In(CN)3 Sn(CN)2 Sb(CN)3 Te(CN)2
Te(CN)4 		ICN Xe
CsCN Ba(CN)2 * Lu(CN)3 Hf Ta W(CN)84− Re Os Ir Pt(CN)42-
Pt(CN)64-
 AuCN
Au(CN)2- 		Hg2(CN)2
Hg(CN)2 		TlCN Pb(CN)2 Bi(CN)3 Po At Rn
Fr Ra ** Lr Rf Db Sg Bh Hs Mt Ds Rg Cn Nh Fl Mc Lv Ts Og
 
* La(CN)3 Ce(CN)3
Ce(CN)4 		Pr(CN)3 Nd Pm Sm(CN)3 Eu(CN)3 Gd(CN)3 Tb Dy(CN)3 Ho(CN)3 Er Tm Yb(CN)3
** Ac(CN)3 Th(CN)4 Pa UO2(CN)2 Np Pu Am Cm Bk Cf Es Fm Md No