We have examined the role of aromaticity in substituent effects for p-stacking interactions. Though the direct through-space interaction model is gaining favor, it is yet to be seen if resonance effects are still negligible when the stabilizing and delocalizing force of aromaticity is missing. We accomplished this by considering stacking interactions of benzenes with aromatic and non-aromatic tautomers of substituted naphthalenes. In order to quantify the effect of aromaticity or nonaromaticity upon substituent effects, substituents were placed at the 5, 6, 7, and 8 positions on the naphthalene, which are at the site of the p-stacking interactions as shown in Figure 1. This study expands our understanding of the properties attributable to aromaticity and when it would be advantageous to use aromatic or nonaromatic molecules when designing systems with p-stacking interactions, and provides fundamental insight into the nature of p-stacking interactions.

Quantifying the role of aromaticity in substituent effects of p-stacking

247th National Meeting (2014)

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