Definition of amides

1. Derivatives of oxoacids RkE(=O)l(OH)m (l not equal to 0) in which an acidic hydroxy group has been replaced by an amino or substituted amino group. Chalcogen replacement analogues are called thio-, seleno- and telluro-amides. Compounds having one, two, or three acyl groups on a given nitrogen are generically included and may be designated as primary, secondary and tertiary amides, respectively. See also e.g. carboxamides , lactams, peptides, phosphoramides, sulfonamides. NOC Rule C-821. E.g. PhC(=O)NH2 benzamide, CH3S(=O)2NMe2 N,N-dimethylmethanesulfonamide, [RC(=O)]2NH secondary amides (see imides), [RC(=O)]3N tertiary amides, PhP(=O)(OH)NH2 phenylphosphonamidic acid.

Note 1. Amides with -NH2, -NHR, and -NR2 groups should not be distinguished by means of the terms primary, secondary, and tertiary. NOC Rule C-824, footnote.

Note 2. Derivatives of certain acidic compounds RnE(OH)m, where E is not carbon (e.g. sulfenic acids, RSOH, phosphinous acids, R2POH) having the structure RnE(NR2)m may be named as amides but do not belong to the class amides proper. NOC Rules C-641.8, D-5.21. E.g. CH3CH2SNH2 ethanesulfenamide or ethylsulfanylamine.

2. The term applies also to metal derivatives of ammonia and amines, in which a cation replaces a hydrogen atom on nitrogen. Such compounds are also called azanides. RNRI Rule RC-83.1.5. E.g. LiN(i-Pr)2 lithium diisopropylamide, synonym lithium diisopropylazanide.

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