Amide

related topics
{acid, form, water}
{language, word, form}

In chemistry, an amide is usually an organic compound that contains the functional group consisting of an acyl group (R-C=O) linked to a nitrogen atom (N). The term refers both to a class of compounds and a functional group within those compounds. The term amide also refers to deprotonated form of ammonia (NH3) or an amine, often represented as anions R2N-. The remainder of this article is about the carbonyl-nitrogen sense of amide. For discussion of these "anionic amides," see the articles sodium amide and lithium diisopropylamide.

Contents

Structure and bonding

The simplest amides are derivatives of ammonia wherein one hydrogen atom has been replaced by an acyl group. The ensemble is generally represented as RC(O)NH2. Closely related and even more numerous are amides derived from primary amines (R'NH2) with the formula RC(O)NHR'. Amides are also commonly derived from secondary amines (R'RNH) with the formula RC(O)NR'R. Amide are usually regarded as derivatives of carboxylic acids in which the hydroxyl group has been replaced by an amine or ammonia.

The lone pair of electrons on the nitrogen is delocalized onto the carbonyl, thus forming a partial double bond between N and the carbonyl carbon. Consequently the nitrogen in amides is not pyramidal. It is estimated that acetamide is described by resonance structure A for 62% and by B for 28%[1]

Nomenclature

Full article ▸

related documents
Glycosidic bond
Vacuole
Chemical compound
Polysaccharide
Nutrient
Gram staining
Phosphorylation
GTPase
Centrosome
Cytochrome
Protein kinase
Phosphate
Alanine
Allosteric regulation
Protein biosynthesis
Calcite
Thulium
Urea cycle
Chemical synthesis
Thermophile
Size exclusion chromatography
Liquid hydrogen
Rubidium
Amorphous solid
Peroxide
Barium
Carl Wilhelm Scheele
Solution
Nitrate
Acetaldehyde