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