Issue 45, 2016
From the journal:

Physical Chemistry Chemical Physics

Cationic CH⋯π interactions as a function of solvation†‡

Bright U. Emenike,*a   Sara N. Bey,a   Ronald A. Spinelle,a   Jacob T. Jones,a   Barney Yoob  and  Matthias Zellerc  

* Corresponding authors

a Department of Chemistry & Physics, State University of New York, 223 Store Hill Road, Old Westbury, NY 11568, USA
E-mail: emenikeb@oldwestbury.edu

b Department of Chemistry, Hunter College, City University of New York, New York, NY 10065, USA

c Department of Chemistry, Purdue University, West Lafayette, IN 47907-2084, USA

Abstract

The energy (ΔG) of a cationic CH⋯π interaction was measured experimentally through the conformational studies of new molecular torsion balances using proton NMR spectroscopy. Each of the molecular balance adopted folded and unfolded conformations for which the ratio of the conformational equilibrium (i.e., folded/unfolded ratio) provided a quantitative measure of the ΔG as a function of solvation. An excellent linear solvation energy relationship between the ΔG values and the Hunter's solvent hydrogen-bond parameters (αs and βs) revealed that electrostatic interaction is the physical origin of the observed conformational preferences in solution.

Graphical abstract: Cationic CH⋯π interactions as a function of solvation

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Article information

DOI
https://doi.org/10.1039/C6CP06800F
Article type
Paper
Submitted
04 Oct 2016
Accepted
21 Oct 2016
First published
21 Oct 2016

Phys. Chem. Chem. Phys., 2016,18, 30940-30945

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Cationic CH⋯π interactions as a function of solvation

B. U. Emenike, S. N. Bey, R. A. Spinelle, J. T. Jones, B. Yoo and M. Zeller, Phys. Chem. Chem. Phys., 2016, 18, 30940 DOI: 10.1039/C6CP06800F

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