Structural Chemistry

, Volume 20, Issue 4, pp 693–697

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

Original Research

DOI: 10.1007/s11224-009-9464-6

Cite this article as:
Hosmane, R.S. & Liebman, J.F. Struct Chem (2009) 20: 693. doi:10.1007/s11224-009-9464-6


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 valuesPeri effectHeterocyclesSteric effectGas phase basicitiesEnthalpy of formation

Copyright information

© Springer Science+Business Media, LLC 2009

Authors and Affiliations

  1. 1.Department of Chemistry and BiochemistryUniversity of MarylandBaltimoreUSA