4.3 Article

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

期刊

STRUCTURAL CHEMISTRY
卷 20, 期 4, 页码 693-697

出版社

SPRINGER/PLENUM PUBLISHERS
DOI: 10.1007/s11224-009-9464-6

关键词

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

资金

  1. National Institutes of Health [1 R01 GM087738-01A1]

向作者/读者索取更多资源

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.

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