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Issue 7, 2015
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How important are dispersion interactions to the strength of aromatic stacking interactions in solution?

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Abstract

In this study, the contributions of London dispersion forces to the strength of aromatic stacking interactions in solution were experimentally assessed using a small molecule model system. A series of molecular torsion balances were designed to measure an intramolecular stacking interaction via a conformational equilibrium. To probe the importance of the dispersion term, the size and polarizability of one of the aromatic surfaces were systematically increased (benzene, naphthalene, phenanthrene, biphenyl, diphenylethene, and diphenylacetylene). After correcting for solvophobic, linker, and electrostatic substituent effects, the variations due to polarizability were found to be an order of magnitude smaller in solution than in comparison to analogous computational studies in vacuo. These results suggest that in solution the dispersion term is a small component of the aromatic stacking interaction in contrast to their dominant role in vacuo.

Graphical abstract: How important are dispersion interactions to the strength of aromatic stacking interactions in solution?

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Publication details

The article was received on 15 Apr 2015, accepted on 15 May 2015 and first published on 18 May 2015


Article type: Edge Article
DOI: 10.1039/C5SC01370D
Chem. Sci., 2015,6, 4358-4364
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    How important are dispersion interactions to the strength of aromatic stacking interactions in solution?

    J. Hwang, B. E. Dial, P. Li, M. E. Kozik, M. D. Smith and K. D. Shimizu, Chem. Sci., 2015, 6, 4358
    DOI: 10.1039/C5SC01370D

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