Title:
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Stabilization of 2,6-Diarylanilinum Cation by Through-Space Cation-pi Interactions
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Author:
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Padial, Joan Simó; Poater i Teixidor, Jordi; Nguyen, D. Thao; Tinnemans, Paul; Bickelhaupt, F. Matthias; Mecinovic, Jasmin
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Other authors:
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Universitat de Barcelona |
Abstract:
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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. |
Subject(s):
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-Cations -Pi (Nombre) -Estabilitzadors -Cations -Pi (Number) -Stabilizing agents |
Rights:
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(c) American Chemical Society , 2017
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Document type:
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Article Article - Accepted version |
Published by:
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American Chemical Society
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