Issue 7, 2012

Rethinking the term “pi-stacking”

Abstract

It has become common to reference “pi-stacking” forces or “pi–pi interactions” when describing the interactions between neighbouring aromatic rings. Here, we review experimental and theoretical literature across several fields and conclude that the terms “pi-stacking” and “pi–pi interactions” do not accurately describe the forces that drive association between aromatic molecules of the types most commonly studied in chemistry or biology laboratories. We therefore propose that these terms are misleading and should no longer be used. Even without these terms, electrostatic considerations relating to polarized pi systems, as described by Hunter and Sanders, have provided a good qualitative starting place for predicting and understanding the interactions between aromatics for almost two decades. More recent work, however, is revealing that direct electrostatic interactions between polarized atoms of substituents as well as solvation/desolvation effects in strongly interacting solvents must also be considered and even dominate in many circumstances.

Graphical abstract: Rethinking the term “pi-stacking”

Article information

Article type
Perspective
Submitted
11 jan 2012
Accepted
23 apr 2012
First published
24 apr 2012

Chem. Sci., 2012,3, 2191-2201

Rethinking the term “pi-stacking”

C. R. Martinez and B. L. Iverson, Chem. Sci., 2012, 3, 2191 DOI: 10.1039/C2SC20045G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements