The ubiquitous nature of cation-aromatic interactions - the stabilizing interactions between cations and the π face of aromatic rings - has led to a variety of applications in science. Although many studies have established the strength of cation-aromatic complexes, the effects of solvation have not been properly investigated, which is surprising considering that the strength of cation-aromatic interactions is known to be modulated by solvation. In this study, the interaction between an <i>N</i>-methyl pyridinium (cation) group and the π face of a benzene ring were experimentally measured in different organic solvents. The experimental cation-aromatic interaction energies were obtained through the conformational studies of synthetic <i>molecular torsional balances,</i> which are capable of measuring weak cation-aromatic interactions in solutions. Subsequently, a relationship between the strength of the cation-aromatic interactions and the physical parameters of the solvating media was established. This study provided important insights into the physical origin and mechanism of the cation-aromatic interactions.

Cationic methyl-aryl interactions as a function of solvation

252nd National Meeting (2016)

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