NH2 is electron acceptor or electron donor?

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Discussion Overview

The discussion centers around the role of the NH2 group in organic chemistry, specifically whether it acts as an electron donor or an electron acceptor. Participants explore the implications of the negative inductive effect and resonance in the context of aromatic compounds.

Discussion Character

  • Debate/contested

Main Points Raised

  • One participant notes that the book states NH2 exhibits a negative inductive effect, which is associated with electron acceptance, while also being described as a ring activating group, which suggests electron donation.
  • Another participant suggests that the terminology used in the book was meant to imply a general rule.
  • A later reply asserts that NH2 can be both an electron donor and acceptor, highlighting that resonance structures between NH2 and benzene lead to it being a ring activator, which they argue dominates over the electronegativity effect.

Areas of Agreement / Disagreement

Participants express differing views on the role of NH2, with some asserting it is both an electron donor and acceptor due to resonance, while others focus on the conflicting definitions presented in the literature. The discussion remains unresolved.

Contextual Notes

Participants reference the negative inductive effect and resonance without fully clarifying the conditions under which each applies, leaving some assumptions unaddressed.

kelvin macks
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i have attached 2 photos here...

the book said the NH2 exhibit negative inductive effect (negative inductive effect means electron acceptor) , and is ring activating group, but ring activating group is electron donor. which is correct?

So NH2 is electron donor or electron acceptor?
 

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They were supposed to imply "generally".
 
Lok said:
They were supposed to imply "generally".

can you explain more detailed?
 
kelvin macks said:
So NH2 is electron donor or electron acceptor?
Both! While NH2 is a negative inductor, there is a resonance structure between NH2 and benzene that makes it a ring activator (the resonance dominates over the electronegativity).

You can find a nice picture of the resonance here: http://www.chm.wright.edu/feld/chm212/eas.pdf
 

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