Amides
Amides are formed from acyl chlorides or related acid derivatives and are molecular examples of amide-link chemistry.
- Functional group
- CONH2
- Also known as
- amide
Overview
Carboxylic acid derivatives containing C(O)-NH2.
Amides are formed from acyl chlorides or related acid derivatives and are molecular examples of amide-link chemistry.
Amides contain nitrogen directly attached to an acyl carbon. Lone-pair delocalisation gives the C-N bond partial double-bond character and makes amides less reactive than acyl chlorides. Peptide bonds and nylon linkages are amides, but molecular context determines their properties.
Identifiers
- Functional group
- CONH2
- Also known as
- amide
Chemical identifiers
- SMILES
- CC(=O)N
Properties
- Amide or amine
- An amide nitrogen is much less basic than a typical aliphatic amine.
- Hydrolysis boundary
- Amide hydrolysis generally needs stronger conditions than ester hydrolysis; enzymes offer specific biological routes.
Related compounds
- Caprolactam
The ring-shaped starting molecule for nylon 6.
- Acetamide
Ethanamide, the simplest two-carbon example of an amide linkage.
- Formamide
Formamide is an organic compound with the molecular formula CH3NO.
- Benzamide
A primary aromatic amide with a carbonyl-bound NH2 group.
- Propanamide
A primary amide with an ethyl group attached to the carbonyl.
- Butanamide
The straight-chain four-carbon primary amide of butanoic acid.
Connected reactions
- Acylation: Acyl chlorides → Amides
Ammonia acylation converts acyl chlorides into amides.
- Anhydride ammonolysis: Acid anhydrides → Amides
Ammonia attacks the anhydride carbonyl to form a tetrahedral intermediate. Carboxylate departure and proton transfer give an amide; excess ammonia also converts the acid co-product into ammonium carboxylate.
References
- Organic Chemistry: Chemistry of AmidesJohn McMurry · OpenStax Organic Chemistry · 2023
Supports functional-group chemistry used to curate the linked examples. Checked 2026-09-16; named examples are applications of textbook scope, without claimed experimental yields.
- Polyamides: nylon 6 and nylon 6,6Chemical Industry Education Centre, University of York
- PubChem Compound Summary: Acetamide (CID 178)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: Formamide (CID 713)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: Benzamide (CID 2331)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: Propanamide (CID 6578)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and selected English aliases retrieved via PUG REST on 2026-09-16. Chinese search names are curated nomenclature translations. Unspecified stereochemistry remains unspecified.
- PubChem Compound Summary: Butanamide (CID 10927)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and selected English aliases retrieved via PUG REST on 2026-09-16. Chinese search names are curated nomenclature translations. Unspecified stereochemistry remains unspecified.