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Nitriles, Isocyanides, and their Derivatives

Rule C-832

By substitutive nomenclature, nitriles are named by one of the following methods:

832.1 - Compounds RCN, in which replaces H3 at the end of the main chain of an acyclic hydrocarbon are denoted by adding "-nitrile" or "-dinitrile" to the name of this hydrocarbon.

Examples to Rule C-832.1

Note: "Nitrile'', here and in Rule C-832.3, denotes the triply bound nitrogen atom, , and not the carbon atom attached to it. Numbering begins with that carbon atom.

832.2 - Compounds RCN, when considered as derived from acids R-COOH whose systematic names end in "-carboxylic acid", are named by changing this ending to "-carbonitrile".

Note: "Carbonitrile'' denotes the group , including the carbon atom contained therein. That carbon atom is excluded from the numbering of a chain to which that group is attached.

Examples to Rule C-832.2

832.3 - Names of compounds RCN, when considered as derived from acids R-COOH having trivial names, are formed by changing the syllables "-oic acid" to "-onitrile", or, if the name of the acid does not end in "-oic acid", then by changing "-ic acid" to "-onitrile".

Examples to Rule C-832.3

(but see Rules C-832.1 and C-832.4)

832.4 - By the radicofunctional procedure, compounds RCN are named by stating the name of the radical R, followed by the name "cyanide" for the group -CN.

Examples to Rule C-832.4

(but see Rules C-832.1 and C-832.3)

832.5 - When the compound contains also a group that has priority over -CN for citation as principal group, the -CN group is named by the prefix "cyano-".

Examples to Rule C-832.5

See Recommendations'93 R-5.7.9

Nitriles, Isocyanides, and Their Derivatives C-833, C-834
Hydroxylamines and Related Compounds C-841, C-842, C-843
Nitroso and Nitro Compounds C-851, C-852
Amine Radical Ions C-861


This HTML reproduction of Sections A, B and C of IUPAC "Blue Book" is as close as possible to the published version [see Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F, and H, Pergamon Press, Oxford, 1979. Copyright 1979 IUPAC.] If you need to cite these rules please quote this reference as their source.

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