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Amides

The amide group is extraordinarily important for life. Proteins and enzymes consist of hundreds or thousands of amide linkages between amino acids. Many everyday life molecules, like for example paracetamol, are amides. Many drugs are amides as well.

Amides of interest: paracetamol, nicotinamide, caffeine and lysergic acid diethylamide (LSD)

There are various functional groups related to amides:

Amide-related compounds: lactams, imides, urea, carbamic acid, carbamates or urethanes and sulfonamides

Examples of amide names: formamide, N,N,2-trimethylpropanamide and 3-carbamoylbenzoic acid

Nomenclature

Bond lengths of acetamide: C=O 1.248 Å and C–N 1.374 Å

Physical and Bond Properties

Protonation of an acid derivative R–CO–L at the carbonyl oxygen and resonance forms of the cation, with the positive charge on the oxygen, the carbon and the L group

Acid-Base Properties

Preparation of amides from acyl halides, anhydrides and esters with amines, and Beckmann rearrangement of an oxime to an amide with its mechanism; cyclopentanone oxime gives the six-membered lactam

Preparation

Hofmann rearrangement of an amide to an amine with loss of CO₂ and its mechanism: amidate, haloamidate, acylnitrene, isocyanate and carbamic acid; scheme of the interconversion R–X → R–COOH → R–NH₂

Reactivity