Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Stabilization of 2,6-Diarylanilinum Cation by Through-Space Cation−π Interactions

Stabilization of 2,6-Diarylanilinum Cation by Through-Space Cation−π Interactions
D. Thao Nguyen, Paul Tinnemans, F. Matthias Bickelhaupt, Jordi Poater, Joan Simó Padial, Jasmin Mecinović
Energetically favorable cation−π interactions play important roles in numerous molecular recognition processes in chemistry and biology. Herein, we present synergistic experimental and computational physical–organic chemistry studies on 2,6-diarylanilines that contain flanking meta/para-substituted aromatic rings adjacent to the central anilinium ion. A combination of measurements of pKa values, structural analyses of 2,6-diarylanilinium cations, and quantum chemical analyses based on the quantitative molecular orbital theory and a canonical energy decomposition analysis (EDA) scheme reveal that through-space cation−π interactions essentially contribute to observed trends in proton affinities and pKa values of 2,6-diarylanilines.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01406

DOI: 10.1021/acs.joc.7b01406

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