I was wondering that how can we compare the basicity of nitrogen in amide to the nitrogen in aniline as in both structures the lone pair on nitrogen is in conjugation as shown below,enter image description here

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Can someone help me?

  • $\begingroup$ Which orbital will be lower in energy and hence more easier to approach and break- the C=O π* or C=C π*? $\endgroup$ – YUSUF HASAN Jan 7 at 2:59

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