, Volume 20, Issue 4, pp 693-697

Paradoxes and paradigms: why is quinoline less basic than pyridine or isoquinoline? A classical organic chemical perspective

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Abstract

An explanation for the reported lower basicity of quinoline as compared with pyridine or isoquinoline has been provided. The competing roles of steric hindrance and solvation effects are discussed along with resonance stabilization of neutral molecules and related ions.