Why are acid amides () significantly weaker bases than aliphatic amines ()? — GOC and Organic Chemistry Basics Chemistry Question

💡 Solution & Explanation

In amides, the strong $-M$ effect of the adjacent carbonyl group pulls the nitrogen's lone pair into resonance ($O=C-N \leftrightarrow ^-O-C=N^+$). This makes the lone pair virtually unavailable to accept an incoming proton, drastically reducing basicity.