Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 18, Pages 9418-9424Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b01406
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- Netherlands Organization for Scientific Research (NWO)
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Energetically favorable cation-pi 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/parasubstituted aromatic rings adjacent to the central anilinium ion. A combination of measurements of pK(a) 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-pi interactions essentially contribute to observed trends in proton affinities and pK(a) values of 2,6-diarylanilines.
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