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Title: Stabilization of 2,6-Diarylanilinum Cation by Through-Space Cation-pi Interactions
Author: Padial, Joan Simó
Poater i Teixidor, Jordi
Nguyen, D. Thao
Tinnemans, Paul
Bickelhaupt, F. Matthias
Mecinovic, Jasmin
Keywords: Cations
Pi (Nombre)
Pi (Number)
Stabilizing agents
Issue Date: 15-Sep-2017
Publisher: American Chemical Society
Abstract: 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.
Note: Versió postprint del document publicat a:
It is part of: Journal of Organic Chemistry, 2017, vol. 82, num. 18, p. 9418-9424
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ISSN: 0022-3263
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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