Question

Account for the following.

Amines are more basic than amides.

Answer 1

In simple amines, the lone pair of electrons is on nitrogen and hence available for protonation. In amides, on the other hand, the electron pair on nitrogen is delocalised to the carboxyl oxygen through resonance and thus it is not available for protonation. So amines are more basic than amides.

\[\begin{array}{cc}
\phantom{}\ce{O}\phantom{.................}\ce{O^-}\phantom{.}\\
\phantom{}||\phantom{..................}|\phantom{...}\\
\ce{\underset{(Amide resonance structure)}{R - C - \overset{\bullet\bullet}{N}H2 <-> R - C = \overset{+}{N}H2}}
\end{array}\]