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why 2,6-Di nitro-N,N-dimethyl anilineis more basic than 3,5-dimethyl-N,N-dimethylaniline

why 2,6-Di nitro-N,N-dimethyl anilineis more basic than 3,5-dimethyl-N,N-dimethylaniline

Grade:12th pass

1 Answers

Arun
25750 Points
6 years ago
In the 3,5-dimethyl isomer, steric effects come into play and influence the acidity.Resonance structures like B in the figure below, that stabilize the phenoxide anion explain why 4-nitrophenol (R=H) is more acidic than phenol. Resonance structure B requires that the nitro group be planar with the aromatic ring. If methyl groups are placed adjacent to the nitro group (R=CH3), the steric interactions between the two methyl groups and the nitro group becomes large and forces the nitro group to rotate out of the aromatic plane, Hence resonance structure B can no longer contribute and the compound is less acidic.

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