An amide nitrogen is electronically coupled to its carbonyl

A primary amine RNH₂ condenses with an acyl chloride R'COCl to form R'CONHR. The nitrogen remains attached to its original R group, and the acyl group comes from the chloride. For example, ethanoyl chloride + methylamine gives N-methylethanamide, CH₃CONHCH₃. A second equivalent of amine, or another base, can remove the HCl formed.

The amide nitrogen lone pair delocalises towards C=O. It is therefore much less available to accept H⁺ than an amine lone pair, and an ordinary amide is essentially neutral in water. The C-N bond has partial double-bond character. This does not mean an amide can never be protonated under strongly acidic conditions; it explains its lack of ordinary aqueous basic behaviour.

For an N-substituted amide, hydrolysis releases the corresponding amine or its ammonium ion instead of necessarily releasing NH₃/NH₄⁺. Reduction retains the N-substituent. For example, CH₃CONHCH₃ reduces to CH₃CH₂NHCH₃, a secondary amine, rather than losing its N-methyl group.