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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.

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Acknowledgment

This research was supported by a grant (to RSH) by the National Institute of General Medical Sciences (Grant # 1 R01 GM087738-01A1) of the National Institutes of Health.

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  1. Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, 1000 Hilltop Circle, Baltimore, MA, 21250, USA

    Ramachandra S. Hosmane & Joel F. Liebman

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  1. Ramachandra S. Hosmane
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  2. Joel F. Liebman
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Correspondence to Ramachandra S. Hosmane.

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Hosmane, R.S., Liebman, J.F. Paradoxes and paradigms: why is quinoline less basic than pyridine or isoquinoline? A classical organic chemical perspective. Struct Chem 20, 693–697 (2009). https://doi.org/10.1007/s11224-009-9464-6

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  • DOI: https://doi.org/10.1007/s11224-009-9464-6

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