Solvent and substituent effects play major roles in modulating the energetics of aromatic interactions, but these phenomena are often viewed as mutually exclusive events. Using a series of imide molecular balances derived from synthesis, we demonstrate, for the first time, that there is a synergy between substituent effects and the hydrogen-bond properties of the solvating media. While Hammett plots show that CH-aryl interactions are driven by electrostatic interactions in polar media, no such correlations were observed in non-polar solvents. This behavior was reconciled quantitatively through Hunter solvation model, which deliver insights into the mechanisms governing the conformational preferences of the imide molecular torsion balances. Our results, based on Hunter solvation model, might contribute to the development of inexpensive solvation models for computational chemistry.<br/>

Synergy between solvation and aromatic substituent effects in CH-aryl interactions

254th National Meeting (2017)

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