Noncovalent interactions involving aromatic rings are pervasive throughout chemical and biological recognition.[1] Of the arene�arene interactions, two geometries are favored: the parallel�displaced and the edge�to�face interactions. The latter is the focus of this research, particularly the effects of substituents, as they modulate the amplitude of the interaction. Exactly how the substituents affect the interaction is still a topic under debate, both in theoretical and experimental studies.[2-5] The investigation was carried out using derivatives of the Wilcox balance.[5] [1] L. M. Salonen, M. Ellermann, F. Diederich, Ang. Chem. Int. Ed. 2011 , 50, 4808�4842.[2] S. E. Wheeler, K. N. Houk, Mol. Phys. 2009 , 107, 749�760.[3] C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc. Perk. T. 2 2001 , 5, 651�669.[4] F. R. Fischer, W. B. Schweizer, F. Diederich, Chem. Commun. 2008 , 4031�4033.[5] S. Paliwal, S. Geib, C. S. Wilcox, J. Am. Chem. Soc. 1994 , 116, 4497�4498.

Molecular torsion balances: Investigation into the nature of substituent effects on the edge–to–face CH/π interaction

245th National Meeting (2013)

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