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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.
The cationic sodium ion, [Na] +, interacts with the anionic cyanoborohydride ion, [BH3(CN)] −. The anionic component of the salt is tetrahedral at the boron atom. The electron-withdrawing cyanide substituent draws electron density away from the negatively charged boron; thus, reducing the electrophilic capabilities of the anionic component. [ 2 ]
Nitriles can also be converted to aldehydes by reduction and hydrolysis. The Stephen aldehyde synthesis uses Tin(II) chloride and hydrochloric acid to yield an aldehyde via the hydrolysis of a resulting iminium salt. Aldehydes can also form using a hydrogen donor followed by in-situ hydrolysis of an imine.
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.
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.
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.
The most important industrial application is the nickel-catalyzed synthesis of adiponitrile (NC−(CH 2) 4 −CN) synthesis from buta-1,3-diene (CH 2 =CH−CH=CH 2). Adiponitrile is a precursor to hexamethylenediamine (H 2 N−(CH 2) 6 −NH 2), which is used for the production of certain kinds of Nylon. The DuPont ADN process to give ...
The structure of a nitrile: the functional group is highlighted blue. In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group.The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH 3 CH 2 C≡N is called "propionitrile" (or propanenitrile). [1]