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Hydrogen isocyanide (HNC) is a linear triatomic molecule with C ∞v point group symmetry.It is a zwitterion and an isomer of hydrogen cyanide (HCN). [2] Both HNC and HCN have large, similar dipole moments, with μ HNC = 3.05 Debye and μ HCN = 2.98 Debye respectively. [3]
Low-temperature photolysis of solids containing HNCO creates the tautomer cyanic acid H−O−C≡N, also called hydrogen cyanate. [15] Pure cyanic acid has not been isolated, and isocyanic acid is the predominant form in all solvents. [2] Sometimes information presented for cyanic acid in reference books is actually for isocyanic acid ...
This reaction is used to destroy odorous isocyanide mixtures. Some isocyanides can polymerize in the presence of Lewis and Bronsted acids. [18] Isocyanides participate in many multicomponent reactions of interest in organic synthesis, two of which are: the Ugi reaction and the Passerini reaction.
A similar reaction is used to make potassium cyanate. Cyanates are produced when cyanides are oxidized. Use of this fact is made in cyanide decontamination processes where oxidants such as permanganate and hydrogen peroxide are used to convert toxic cyanide into less-toxic cyanate.
Glycolonitrile is produced by reacting formaldehyde with hydrogen cyanide at near-neutral pH, but with small amounts of catalytic base. [5] Glycolonitrile polymerizes under alkaline conditions above pH 7.0. As the product of polymerization is an amine with a basic character, the reaction is self-catalysed, gaining in speed with ongoing conversion.
The main reaction exhibited by cyanamide involves additions of compounds containing an acidic proton. Water, hydrogen sulfide, and hydrogen selenide react with cyanamide to give urea, thiourea, and selenourea, respectively: H 2 NCN + H 2 E → H 2 NC(E)NH 2 (E = O, S, Se)
Cyanogen is typically generated from cyanide compounds. One laboratory method entails thermal decomposition of mercuric cyanide: . 2 Hg(CN) 2 → (CN) 2 + Hg 2 (CN) 2 Or, one can combine solutions of copper(II) salts (such as copper(II) sulfate) with cyanides; an unstable copper(II) cyanide is formed which rapidly decomposes into copper(I) cyanide and cyanogen.
Acetylenic substrates undergo the reaction; however the scope of this reaction is limited and yields are often low. [5] 1,4-Addition to imines has been observed in a few cases, although imines are often base labile. [5] Esters, [7] nitriles, [5] and other carbonyl derivatives also undergo conjugative hydrocyanation. When alkali metal cyanides ...