Editing Amide (section)

===Basicity===
Compared to [[amine]]s, amides are very weak [[base (chemistry)|base]]s. While the [[conjugate acid]] of an [[amine]] has a [[pKa|p''K''<sub>a</sub>]] of about 9.5, the [[conjugate acid]] of an amide has a p''K''<sub>a</sub> around −0.5. Therefore, compared to amines, amides do not have [[acid–base]] properties that are as noticeable in [[water]]. This relative lack of basicity is explained by the withdrawing of electrons from the amine by the carbonyl. On the other hand, amides are much stronger [[Base (chemistry)|base]]s than [[carboxylic acid]]s, [[ester]]s, [[aldehyde]]s, and [[ketone]]s (their conjugate acids' p''K''<sub>a</sub>s are between −6 and −10).

The proton of a primary or secondary amide does not dissociate readily; its p''K''<sub>a</sub> is usually well above 15. Conversely, under extremely acidic conditions, the carbonyl [[oxygen]] can become protonated with a p''K''<sub>a</sub> of roughly −1. It is not only because of the positive charge on the nitrogen but also because of the negative charge on the oxygen gained through resonance.