Structural Chemistry

, Volume 20, Issue 4, pp 693–697 | Cite as

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

Original Research


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.


pKa values Peri effect Heterocycles Steric effect Gas phase basicities Enthalpy of formation 


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© Springer Science+Business Media, LLC 2009

Authors and Affiliations

  1. 1.Department of Chemistry and BiochemistryUniversity of MarylandBaltimoreUSA

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