3.16 Nitriles

Nitriles contain a C≡N group. This means they are organic cyanides, since HC≡N is hydrogen cyanide. But nitriles generally don't have the extreme toxicity of cyanides.

Nitriles are often named similarly to the carboxylic acids with the same carbon chain lengths, such as acetonitrile CH₃CN (same as CH₃C≡N) by analogy with acetic acid, and propionitrile CH₃CH₂CN by analogy with propionic acid. Acrylonitrile CH₂=CHCN, analogous to acrylic acid CH₂=CHCO₂H, is a precursor to some plastics.

There is no formyl nitrile because that would just be HCN, and HCN is toxic and inorganic, unlike a nitrile.

Related to nitriles are cyanates, which have an -OC≡N group. There are also isocyanates, where the group is rearranged as -N=C=O.

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