Title: amides
Long Title: IUPAC Gold Book - amides
DOI: 10.1351/goldbook.A00266
Status: current

Definition
Derivatives of oxoacids $\ce{R_{k}E(=O)_{l}(OH)_{m}}\ (l \neq 0)$ in which an acidic hydroxy group has been replaced by an amino or substituted amino group.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, e.g.  benzamide, N,N-dimethylmethanesulfonamide,  secondary amides (see imides),  tertiary amides,  phenylphosphonamidic acid.Notes:Amides with $\ce{NH2}$, $\ce{NHR}$ and $\ce{NR2}$ groups should not be distinguished by means of the terms primary, secondary and tertiary.Derivatives of certain acidic compounds $\ce{R_{n}E(OH)_{m}}$, where $\ce{E}$ is not carbon (e.g. sulfenic acids, $\ce{RSOH}$, phosphinous acids, $\ce{R2POH)}$, having the structure $\ce{R_{n}E(NR2)_{m}}$ may be named as amides but do not belong to the class amides proper, e.g. $\ce{CH3CH2SNH2}$ ethanesulfenamide or ethylsulfanylamine.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, e.g.  lithium diisopropylamide, synonym lithium diisopropylazanide.See also: carboxamides, lactams, peptides, phosphoramides, sulfonamides

Related Terms
- acyl groups: https://goldbook.iupac.org//terms/view/A00123
- amines: https://goldbook.iupac.org//terms/view/A00274
- carboxamides: https://goldbook.iupac.org//terms/view/C00850
- cation: https://goldbook.iupac.org//terms/view/C00907
- imides: https://goldbook.iupac.org//terms/view/I02948
- lactams: https://goldbook.iupac.org//terms/view/L03435
- oxoacids: https://goldbook.iupac.org//terms/view/O04374
- peptides: https://goldbook.iupac.org//terms/view/P04479
- phosphinous acids: https://goldbook.iupac.org//terms/view/P04556
- phosphoramides: https://goldbook.iupac.org//terms/view/P04566
- sulfenic acids: https://goldbook.iupac.org//terms/view/S06096
- sulfonamides: https://goldbook.iupac.org//terms/view/S06114
- thio: https://goldbook.iupac.org//terms/view/T06347

Source
- PAC, 1995, 67, 1307. 'Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)' on page 1315 (https://doi.org/10.1351/pac199567081307)

Related Reference
- PAC, 1993, 65, 1357. 'Revised nomenclature for radicals, ions, radical ions and related species (IUPAC Recommendations 1993)' on page 1357 (https://doi.org/10.1351/pac199365061357)

Other Outputs
- html: https://goldbook.iupac.org/terms/view/A00266/html
- json: https://goldbook.iupac.org/terms/view/A00266/json
- xml: https://goldbook.iupac.org/terms/view/A00266/xml

Citation: Citation: 'amides' in IUPAC Compendium of Chemical Terminology, 5th ed. International Union of Pure and Applied Chemistry; 2025. Online version 5.0.0, 2025. 10.1351/goldbook.A00266
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Accessed: 2026-05-06T15:19:12+00:00