ACD/Name

Specific Classes of Compounds

R-5.7.9 Nitriles, isocyanides and related compounds

R-5.7.9.1 Nitriles. Compounds with the general structure are called "nitriles" or "cyanides" generically and may be named substitutively in a manner closely related to that for acids and other related compounds. Acyclic mono- and dinitriles in which may be considered to have replaced the group(s) of an acid named by an "-oic acid" or "-dioic acid" suffix are named by adding the suffix "-nitrile" or "-dinitrile" to the name of the hydrocarbon from which the acid name was derived.

Examples to R-5.7.9.1

Nitriles in which may be considered to have replaced of an acid with a retained trivial name (see R-9.1, Table 28(a)) are named by changing the "-ic acid", or "-oic acid" ending of the name of the acid to "-onitrile".

Examples to R-5.7.9.1

Nitriles in which may be considered to have replaced the group(s) of an acid named by a "-carboxylic acid" suffix are named by replacing that suffix with "carbonitrile".

Examples to R-5.7.9.1

Functional class names for nitriles of the general structure are formed by citing the prefix name for the group R followed by the class name "cyanide" as a separate word. Compounds with a general structure such as and may be named similarly.

Examples to R-5.7.9.1

When a group is present that has priority for citation as the principal characteristic group or when all groups cannot be expressed as the principal characteristic group, groups are described by the prefix "cyano-".

Examples to R-5.7.9.1

R-5.7.9.2 Cyanide-related compounds. Compounds containing a group X listed in the first column of Table 16 are named by methods analogous to those described for halides (see R-5.3.1); the functional class names given in the second column of the Table are used in place of "halide" or the prefixes given in the third column of the Table in place of "halo-".

Examples to R-5.7.9.2

R-5.7.9.3 Nitrile oxides. Compounds with the general structure have the generic name "nitrile oxides". In specific cases, the class name "oxide" is added as a separate word after a nitrile name, but not a cyanide name.

Example to R-5.7.9.3


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This HTML reproduction is as close as possible to the published version [see IUPAC, Commission on Nomenclature of Organic Chemistry. A Guide to IUPAC Nomenclature of Organic Compounds (Recommendations 1993), 1993, Blackwell Scientific publications, Copyright 1993 IUPAC]. If you need to cite these rules please quote this reference as their source.

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