ACD/Name

Specific Classes of Compounds

R-5.7.8 Amides, imides, and hydrazides

R-5.7.8.1 Monoacyl derivatives of ammonia (primary amides) are named by replacing the suffixes "-oic acid", "-ic acid", or "-carboxylic acid" of the name of the acid corresponding to the acyl group by "-amide" or "-carboxamide". The substituent prefix corresponding to is "carbamoyl-".

Examples to R-5.7.8.1

(see R-5.7.1.2.2)

Some trivial names are retained (see R-9.1, Table 28(a)).

Substituted primary amides with general structures such as , . and the corresponding sulfonamides, are named by citing the substituents R' and R" as prefixes (but see below for N-phenyl derivatives).

Examples to R-5.7.8.1

N-Phenyl derivatives of primary amides are called "anilides" and may be named using the suffix "-anilide" in place of the suffix "-amide". Locants for substituents in the N-phenyl ring are primed.

Examples to R-5.7.8.1

Alternatively, an N-acyl group may be named as a N-substituent of an amine. This method is used mainly for N-derivatives of nitrogenous heterocycles.

Example to R-5.7.8.1

When a group having preference for citation as a principal characteristic group is present, the group of an N-substituted amide may be treated as a substituent of the compound HR'. The group may be expressed as a substituent by changing the "-amide" or "-carboxamide" suffix of the amide name to "amido-" or "carboxamido-", respectively, or alternatively, by the appropriate "acylamino-" preix.

Examples to R-5.7.8.1

R-5.7.8.2 Symmetrical diacyl and triacyl derivatives of ammonia, i.e., and respectively, are named as di- and triacyl derivatives of the parent hydride azane, or as di- and triacylamines.

Examples to R-5.7.8.2

The trivial names diacetamide and triacetamide for the compounds and , respectively, and dibenzamide and tribenzamide for and , respectively, have been used but are not included in these recommendations for use in naming carbon-substituted derivatives.

Unsymmetrical di- and triacyl derivatives of ammonia, such as , , and , may be named (a) on the basis of the parent hydride azane; (b) as a diacylamine, a diacylalkyl- (or aryl, etc.) amine, or a triacylamine; or (c) as alkyl (or aryl, etc.) or acyl derivatives of a primary amide (see R-5.7.8.1), diacetamide, or dibenzamide.

Examples to R-5.7.8.2

R-5.7.8.3 Imides are compounds containing the structural grouping and may be considered as nitrogen analogues of anhydrides or as diacyl derivatives of ammonia. Acyclic imides are named according to R-5.7.8.2. Cyclic imides are named by replacing the suffixes "-dioic acid", "-ic acid", or "-dicarboxylic acid" of the corresponding dibasic acid by "-imide" or "-dicarboximide". They can also be named as heterocycles.

Examples to R-5.7.8.3

R-5.7.8.4 Hydrazides. Monoacyl derivatives of the parent hydride diazane (hydrazine), , have the generic name "hydrazides" and are named by replacing the "-ic acid" or "-oic acid" suffix of the name of the acid by "-ohydrazide" or the suffix "-carboxylic acid" by "-carbohydrazide".

Examples to R-5.7.8.4

Alkyl, aryl, cycloalkyl, etc., substituents on the nitrogen atoms of hydrazides are described by the appropriate prefix names using the locants N- (or 1'-) for the imino nitrogen atom and N'- (or 2'-) for the amino nitrogen atom. Hydrazide derivatives may also be named as derivatives of the parent hydride diazane (hydrazine).

Examples to R-5.7.8.4

Diacyl, triacyl and tetraacyl derivatives of hydrazides are named on the basis of the parent hydride diazane (hydrazine).

Examples to R-5.7.8.4

When a group having priority for citation as a principal characteristic group is present, a hydrazide group is expressed by the prefix "acyldiazanyl-" (acylhydrazino-). Locants for positions on the hydrazino- group are N- (or 1-) for the nitrogen atom adjacent to the free valence position and N'- (or 2-) for the other nitrogen atom.

Examples to R-5.7.8.4

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R-5.7.9 Nitriles, isocyanides and related compounds

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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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