Amide

This article is about organic amides with the formula RC(=O)NR′R″. For the anion NH−2, see Azanide. For other uses, see Amide (functional group).
Not to be confused with imide.

General structure of an amide (specifically, a carboxamide)
Formamide, the simplest amide
Asparagine (zwitterionic form), an amino acid with a side chain (highlighted) containing an amide group

In organic chemistry, an amide,[1][2][3] also known as an organic amide or a carboxamide, is a compound with the general formula R−C(=O)−NR′R″, where R, R', and R″ represent any group, typically organyl groups or hydrogen atoms.[4][5] The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, as in asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid (R−C(=O)−OH) with the hydroxyl group (−OH) replaced by an amine group (−NR′R″); or, equivalently, an acyl (alkanoyl) group (R−C(=O)−) joined to an amine group.

Common of amides are formamide (H−C(=O)−NH2), acetamide (H3C−C(=O)−NH2), benzamide (C6H5−C(=O)−NH2), and dimethylformamide (H−C(=O)−N(−CH3)2). Some uncommon examples of amides are N-chloroacetamide (H3C−C(=O)−NH−Cl) and chloroformamide (Cl−C(=O)−NH2).

Amides are qualified as primary, secondary, and tertiary according to whether the amine subgroup has the form −NH2, −NHR, or −NRR', where R and R' are groups other than hydrogen.[5]

  1. ^ "Amide definition and meaning - Collins English Dictionary". www.collinsdictionary.com. Retrieved 15 April 2018.
  2. ^ "amide". The American Heritage Dictionary of the English Language (5th ed.). HarperCollins.
  3. ^ "amide - Definition of amide in English by Oxford Dictionaries". Oxford Dictionaries – English. Archived from the original on 2 April 2015. Retrieved 15 April 2018.
  4. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "amides". doi:10.1351/goldbook.A00266
  5. ^ a b Fletcher, John H. (1974). "Chapter 21: Amides and Imides". Nomenclature of Organic Compounds: Principles and Practice. Vol. 126. Washington, DC: American Chemical Society. pp. 166–173. doi:10.1021/ba-1974-0126.ch021. ISBN 9780841201910.