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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.
Cyanide is unstable in water, but the reaction is slow until about 170 °C. It undergoes hydrolysis to give ammonia and formate, which are far less toxic than cyanide: [14] CN − + 2 H 2 O → HCO − 2 + NH 3. Cyanide hydrolase is an enzyme that catalyzes this reaction.
The cyanate ion can bridge between two metal atoms by using both its donor atoms. For example, this structure is found in the compound [Ni 2 (NCO) 2 2](BPh 4) 2. In this compound both the Ni−N−C unit and Ni−O−C unit are bent, even though in the first case donation is through the nitrogen atom. [16]
Cyanamides are more acidic and less basic than alkylamines, protonating at the terminal nitrogen. However, nickel(0) complexes are known in which nickel coordinates to both nitrogen atoms. When protonated, the central carbon is very electrophilic, and will add a variety of nucleophiles. [21]: 1393–1395, 1399
A CN bond is strongly polarized towards nitrogen (the electronegativities of C and N are 2.55 and 3.04, respectively) and subsequently molecular dipole moments can be high: cyanamide 4.27 D, diazomethane 1.5 D, methyl azide 2.17, pyridine 2.19. For this reason many compounds containing CN bonds are water-soluble.
Upon hydrolysis, an amide converts into a carboxylic acid and an amine or ammonia (which in the presence of acid are immediately converted to ammonium salts). One of the two oxygen groups on the carboxylic acid are derived from a water molecule and the amine (or ammonia) gains the hydrogen ion. The hydrolysis of peptides gives amino acids.
The oxygen atoms are arranged at the vertices of a regular octahedron centered on the sodium ion. First and second solvation shells of an octahedral aqua ion. Up to 12 water molecules may be present in the second shell (only two are shown in this diagram) linked by hydrogen bonds to the molecules in the first shell.
The application exploits the high affinity of gold(I) for cyanide, which induces gold metal to oxidize and dissolve in the presence of air (oxygen) and water, producing the salt sodium dicyanoaurate (or sodium gold cyanide) (NaAu(CN) 2): [4] 4 Au + 8 NaCN + O 2 + 2 H 2 O → 4 Na[Au(CN) 2] + 4 NaOH