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Basicity of (2,6-Pyridino)paracyclophanes: Lone Pair–π, Cation–π, and Solvation Effects

Authors

  • Prof. Kim K. Baldridge,

    Corresponding author
    1. Organic Chemistry Institute, University of Zurich, Winterthurerstrasse 190, 8057 Zurich (Switzerland)
    • Organic Chemistry Institute, University of Zurich, Winterthurerstrasse 190, 8057 Zurich (Switzerland)
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  • Prof. Franco Cozzi,

    Corresponding author
    1. Dipartimento di Chimica Organica e Industriale, Universitá degli Studi di Milano via Golgi 19, 20133 Milano (Italy)
    • Dipartimento di Chimica Organica e Industriale, Universitá degli Studi di Milano via Golgi 19, 20133 Milano (Italy)
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  • Prof. Jay S. Siegel

    Corresponding author
    1. Organic Chemistry Institute, University of Zurich, Winterthurerstrasse 190, 8057 Zurich (Switzerland)
    • Organic Chemistry Institute, University of Zurich, Winterthurerstrasse 190, 8057 Zurich (Switzerland)
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  • We thank the Swiss National Science Foundation and the Universitá degli Studi di Milano for research support.

Abstract

original image

Lost in solvation: A study of the basicity of (2,6-pyridino)paracyclophanes (see picture; C light blue, N blue, S orange, F yellow, H green) reveals the importance of bulk solvation compared to cation–π effects in determining the relative stability of cations.

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