Nitrile

Nitrile is a type of organic compound that has a cyanide group (-C≡N) which is bonded to a carbon atom. Nitriles are found in many useful compounds, including synthetic rubber and pharmaceuticals.

Structure and bonding

The C≡N functional group in a nitrile is linear, with a 180° bond angle. The carbon atom in the C≡N bond is sp hybridized, and the nitrogen atom is sp hybridized. The carbon-nitrogen triple bond is very strong and has a bond length of 1.16 Å.

Nomenclature

The IUPAC nomenclature for nitriles designates them as derivatives of carboxylic acids by changing '-ic acid' to '-onitrile', or '-carboxylic acid' to '-carbonitrile'. For example, the nitrile of acetic acid is acetonitrile (CH3CN).

Preparation

Nitriles can be prepared by several methods, including the dehydration of amides, the reaction of amines with cyanogen chloride, and the reaction of alcohols with hydrogen cyanide.

Reactions

Nitriles undergo various reactions, including hydrolysis to carboxylic acids, reduction to primary amines, and reaction with Grignard reagents to ketones.

Uses

Nitriles are used in the production of synthetic rubbers, plastics, and pharmaceuticals. They are also used as solvents and in the synthesis of organic compounds.

See also

• Cyanide
• Amide
• Carboxylic acid
• IUPAC nomenclature of organic chemistry

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