Nitrile

The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH3CH2C≡N is called "propionitrile" (or propanenitrile).

[6] Around 1832 benzonitrile, the nitrile of benzoic acid, was prepared by Friedrich Wöhler and Justus von Liebig, but due to minimal yield of the synthesis neither physical nor chemical properties were determined nor a structure suggested.

In 1834 Théophile-Jules Pelouze synthesized propionitrile, suggesting it to be an ether of propionic alcohol and hydrocyanic acid.

[7] The synthesis of benzonitrile by Hermann Fehling in 1844 by heating ammonium benzoate was the first method yielding enough of the substance for chemical research.

Fehling determined the structure by comparing his results to the already known synthesis of hydrogen cyanide by heating ammonium formate.

In the Kolbe nitrile synthesis, alkyl halides undergo nucleophilic aliphatic substitution with alkali metal cyanides.

In general, metal cyanides combine with alkyl halides to give a mixture of the nitrile and the isonitrile, although appropriate choice of counterion and temperature can minimize the latter.

Aldehydes react readily with hydroxylamine salts, sometimes at temperatures as low as ambient, to give aldoximes.

These can be dehydrated to nitriles by simple heating,[15] although a wide range of reagents may assist with this, including triethylamine/sulfur dioxide, zeolites, or sulfuryl chloride.

[17] Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions.

On the other hand, the acid catalyzed reactions requires a careful control of the temperature and of the ratio of reagents in order to avoid the formation of polymers, which is promoted by the exothermic character of the hydrolysis.

[31] In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine.

Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the C≡N group.

Key to the exceptional nucleophilicity is the small steric demand of the C≡N unit combined with its inductive stabilization.

These features make nitriles ideal for creating new carbon-carbon bonds in sterically demanding environments.

Examples include tetrakis(acetonitrile)copper(I) hexafluorophosphate ([Cu(MeCN)4]+) and bis(benzonitrile)palladium dichloride (PdCl2(PhCN)2).

[42]: 1700 The heavier nitrile sulfides are extremely reactive and rare, but temporarily form during the thermolysis of oxathiazolones.

Mandelonitrile, a cyanohydrin produced by ingesting almonds or some fruit pits, releases hydrogen cyanide and is responsible for the toxicity of cyanogenic glycosides.

The types of pharmaceuticals containing nitriles are diverse, from vildagliptin, an antidiabetic drug, to anastrozole, which is the gold standard in treating breast cancer.