Chemical Science· 2012Q1· Review
Rethinking the term “pi-stacking”
- 1,653citations
- Q1SCImago
- 2012year
Short summary
The commonly used terms “pi-stacking” and “pi–pi interactions” are misleading and should be abandoned as they do not accurately describe the forces driving association between aromatic molecules.
AI-generated from the title and abstract; the full text is not read.
Key points
- "Pi-stacking" and "pi–pi interactions" are concluded to be inaccurate terms for forces between aromatic molecules.
- Existing electrostatic models (Hunter and Sanders) provide a qualitative basis but are insufficient.
- Direct electrostatic interactions between polarized substituents and solvation/desolvation effects are increasingly recognized as dominant factors.
- The paper advocates for the discontinuation of the terms "pi-stacking" and "pi–pi interactions".
AI-generated from the title and abstract; the full text is not read.
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.
The authors' abstract, as published at the source. Chemical Science, 2012 · DOI ↗
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Field: Physical and Theoretical Chemistry
Physical and Theoretical ChemistryChemistry