Grade 12th passOrganic Chemistry
Why isoquinoline is more basic than quinoline? Give reason.
Why isoquinoline is more basic than quinoline? Give reason.
2 Answers
This is not due to the inductive effect, but rather, due to solvation. The positive charge of quinoline on the nitrogen is harder to solvate due to steric repulsion of the nearby ring, whereas in pyridine, the small hydrogen atoms in place do not pose a strong steric hindrance for the solvation of the ion.
The N of isoquinoline can not take part in resonance so it's lone pair is free to donate rather than the lone pair of quinoline. So isoquinoline can act as a better base.
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