NH2 is electron acceptor or electron donor?

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SUMMARY

The NH2 group functions as both an electron donor and an electron acceptor, depending on the context. It exhibits a negative inductive effect, indicating its role as an electron acceptor, while also acting as a ring-activating group due to resonance structures with benzene, which dominate over its electronegativity. This dual behavior is crucial for understanding its reactivity in electrophilic aromatic substitution reactions.

PREREQUISITES
  • Understanding of inductive effects in organic chemistry
  • Familiarity with resonance structures and their implications
  • Knowledge of electrophilic aromatic substitution mechanisms
  • Basic concepts of benzene chemistry
NEXT STEPS
  • Study the concept of inductive effects in organic compounds
  • Explore resonance structures and their impact on molecular behavior
  • Learn about electrophilic aromatic substitution reactions in detail
  • Investigate the role of substituents in aromatic chemistry
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Chemistry students, organic chemists, and anyone interested in the reactivity of aromatic compounds will benefit from this discussion.

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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