Nitrile

A nitrile is any organic compound that has a −C≡N functional group. The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in the latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.

Inorganic compounds containing the −C≡N group are not called nitriles, but cyanides instead. Though both nitriles and cyanides can be derived from cyanide salts, most nitriles are not nearly as toxic.

Structure and basic properties

The N-C-C geometry is linear in nitriles, reflecting the sp hybridization of the triply bonded carbon. The C-N distance is short at 1.16 Å, consistent with a triple bond. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high dielectric constants, often in the 30s.