Substituents and heteroatoms can be used to tune the strength and geometry of non-covalent interactions, which can provide a means of controlling many supramolecular assembly phenomena. Exploiting these means of control will require a sound understanding of the nature of substituent and heteratom effects.  Traditional models of substituent effects in p-stacking interactions, for example, are cast in terms of substituent-induced changes in the p-system of the substituted ring. We provide an alternative model based on direct, local interactions between the substituents and the proximal vertex of the other ring.  This simple view can explain interaction energies of a myriad of stacked systems, and provides pathways for the control of the local orientation of stacked discotic systems.  Recent results for p-stacking interaction of heteroaromatic systems are also presented.

Understanding the impact of substituents and heteroatoms on non-covalent interactions involving aromatic rings

245th National Meeting (2013)

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