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+ Resonance
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M Hess

Amine group - electron donating or withdrawing group?

David Dowler  Follow

When the atome of nitrogen participates through its free electron pair in resonance, the amine group plays the role of a donating group by conjugation. When it cannot participate in conjugation through resonance, the amine groupe plays the role of inductive electron-withdrawer group, due to the higher electronegativity of nitrogen atom compared to carbon atom.

When the amine group plays the role of electron donating group through conjugation, its inductive withdrawing effect (still existing) is weaker and masked by the first effect.

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