What Factors Influence the Basicity Order of Substituted Anilines?

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SUMMARY

The discussion focuses on the basicity order of substituted anilines, specifically comparing p-methyl aniline, m-methyl aniline, aniline, and o-methyl aniline. The established order is p-methyl aniline > m-methyl aniline > aniline > o-methyl aniline, attributed to the effects of hyperconjugation and inductive effects. Additionally, the basicity order for nitro-substituted anilines is aniline > m-nitro aniline > p-nitro aniline > o-nitro aniline, with the ortho position being least basic due to steric hindrance and resonance effects. The discussion raises questions about the applicability of the ortho effect to all substituents.

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  • Understanding of basicity concepts in organic chemistry
  • Familiarity with substituent effects such as hyperconjugation and inductive effects
  • Knowledge of resonance structures and their impact on molecular stability
  • Experience with analyzing structure-activity relationships in substituted anilines
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  • Research the concept of hyperconjugation in organic compounds
  • Study the inductive effect of various substituents on aromatic compounds
  • Examine the ortho effect and its implications for different functional groups
  • Explore the basicity of other substituted amines and their comparative analysis
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Chemistry students, organic chemists, and researchers interested in the effects of substituents on the basicity of anilines and related compounds.

sachin123
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Hey folks.
The orders given are stated in my book.I'm here to ask why.

basicity: p-methyl aniline>m-()>aniline>o-()
p exerts hyperconjugation and +I,m only +I ,but ortho exerts hyperconjugation and higher +I.
Shouldn't o-methyl aniline have high basicity?

basicity: aniline>m-nitro()>p-nitro()>o-nitro()
Why is o- at last?Shouldn't it move NH2 out of plane so that no -R takes place?

And is the ortho effect applicable to all substituents?Can you clear this for me?
Thank You.
 
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