Amide

Overview

The amide anion is the conjugate base of ammonia, NH₂^-. It is an extremely strong base, due to the extreme weakness of ammonia as a Bronsted acid.

Amides are the members of a group of chemical compounds containing nitrogen. Specifically, an amide is a derivative of a carboxylic acid in which the hydroxyl group has been replaced by an amine or ammonia.

Compounds in which a hydrogen atom on nitrogen from ammonia or an amine is replaced by a metal cation are also known as amides or azanides.

The amide functional group is:

Synthesis and breakdown

Amide formation plays a role in the synthesis of some condensation polymers, such as nylon. Their breakdown is possible via amide hydrolysis.

Amide linkages

An amide linkage is kinetically stable to hydrolysis. Amide linkages in a biochemical context are called peptide linkages. Amide linkages constitute a defining molecular feature of proteins, the secondary structure of which is due in part to the hydrogen bonding abilities of amides.

Derivatives

Sulfonamides are analogs of amides in which the atom double bonded to oxygen is sulfur rather than carbon.

Naming

• Example: CH₃CONH₂ is named acetamide or ethanamide
• Other examples: propan-1-amide, N,N-dimethylpropanamide
• For more detail see IUPAC_nomenclature#Amines_and_Amides
  

  References

• IUPAC Compendium of Chemical Terminology