Original Research

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

  • Ramachandra S. HosmaneAffiliated withDepartment of Chemistry and Biochemistry, University of Maryland Email author 
  • , Joel F. LiebmanAffiliated withDepartment of Chemistry and Biochemistry, University of Maryland

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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.

Keywords

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