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  1. Derivatives of oxoacidsRkE(=O)l(OH)m (l ≠ 0) in which an acidic hydroxy group has been replaced by an amino or substituted amino group.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.
    A00266-1
    benzamide,
    A00266-2
    N,N-dimethylmethanesulfonamide,
    A00266-3
    secondary amides (see imides ),
    A00266-4
    tertiary amides,
    A00266-5
    phenylphosphonamidic acid.
    Notes:
    1. Amides with NH2, NHR and NR2 groups should not be distinguished by means of the terms primary, secondary and tertiary.
    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, 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, e.g.
    A00266-6
    lithium diisopropylamide, synonym lithium diisopropylazanide.
Source:
PAC, 1995, 67, 1307 (Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)) on page 1315
See also:
PAC, 1993, 65, 1357 (Revised nomenclature for radicals, ions, radical ions and related species (IUPAC Recommendations 1993)) on page 1357
InChI=1/C6H8NO2P/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H3,7,8,9)/f/h8H,7H2
InChI=1/C3H9NO2S/c1-4(2)7(3,5)6/h1-3H3
InChI=1/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9)/f/h8H2
InChI=1/C6H14N.Li/c1-5(2)7-6(3)4;/h5-6H,1-4H3;/q-1;+1
HRQOQAVEPWMWFE-XLKFYZMLCP
WCFDSGHAIGTEKL-UHFFFAOYAG
KXDAEFPNCMNJSK-FSHFIPFOCL
ZCSHNCUQKCANBX-UHFFFAOYAP
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IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A.Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. https://doi.org/10.1351/goldbook.
Last update: 2008-10-07; version: 2.0.2.
DOI of this term: https://doi.org/10.1351/goldbook.A00266.
Original PDF version (may be out of date): http://www.iupac.org/goldbook/A00266.pdf.
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