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

Joan Simó Padial, Jordi Poater, D. Thao Nguyen, Paul Tinnemans, F. Matthias Bickelhaupt*, Jasmin Mecinović

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)9418-9424
Number of pages7
JournalJournal of Organic Chemistry
Volume82
Issue number18
DOIs
Publication statusPublished - 15 Sep 2017

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