question archive Consider structures, ##RC(=O)NH(R)## versus ##RC(-O^-)=N^+HR## The second structure is the amide equivalent of an enolate anion
Consider structures, ##RC(=O)NH(R)## versus ##RC(-O^-)=N^+HR## The second structure is the amide equivalent of an enolate anion
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Consider structures, ##RC(=O)NH(R)## versus ##RC(-O^-)=N^+HR##
The second structure is the amide equivalent of an enolate anion. Evidently, more electron is concentrated on the oxygen rather than the nitrogen centre, hence the oxygen is more basic. Even though the nitrogen has a formal lone pair, it tends to donate electron density to the oxygen centre.
