Communication

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

  1. Prof. Kim K. Baldridge1,*,
  2. Prof. Franco Cozzi2,*,
  3. Prof. Jay S. Siegel1,*

Article first published online: 15 FEB 2012

DOI: 10.1002/anie.201108545

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 12, pages 2903–2906, March 19, 2012

Additional Information

How to Cite

Baldridge, K. K., Cozzi, F. and Siegel, J. S. (2012), Basicity of (2,6-Pyridino)paracyclophanes: Lone Pair–π, Cation–π, and Solvation Effects . Angew. Chem. Int. Ed., 51: 2903–2906. doi: 10.1002/anie.201108545

Author Information

  1. 1

    Organic Chemistry Institute, University of Zurich, Winterthurerstrasse 190, 8057 Zurich (Switzerland)

  2. 2

    Dipartimento di Chimica Organica e Industriale, Universitá degli Studi di Milano via Golgi 19, 20133 Milano (Italy)

*Organic Chemistry Institute, University of Zurich, Winterthurerstrasse 190, 8057 Zurich (Switzerland)

  1. †

    We thank the Swiss National Science Foundation and the Universitá degli Studi di Milano for research support.

Publication History

  1. Issue published online: 13 MAR 2012
  2. Article first published online: 15 FEB 2012
  3. Manuscript Revised: 31 DEC 2011
  4. Manuscript Received: 4 DEC 2011

Funded by

  • Swiss National Science Foundation
  • Universitá degli Studi di Milano

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Keywords:

  • π interactions;
  • basicity;
  • cations;
  • cyclophanes;
  • solvent effects
Thumbnail image of graphical abstract

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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