Modulating Weak Interactions for Molecular Recognition: A Dynamic Combinatorial Analysis for Assessing the Contribution of Electrostatics to the Stability of CH–π Bonds in Water1. Issue 14 (9th February 2015)

• Record Type: Journal Article
• Authors: Jiménez‐Moreno, Ester; Gómez, Ana M.; Bastida, Agatha; Corzana, Francisco; Jiménez‐Oses, Gonzalo; Jiménez‐Barbero, Jesús; Asensio, Juan Luis
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 14(2015)
• Page Start: 4344
• Page End: 4348
• Publication Date: 2015-02-09
• Subjects: CH–π interactions -- drug design -- dynamic combinatorial chemistry -- molecular recognition; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201411733
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Electrostatic and charge‐transfer contributions to CH–π complexes can be modulated by attaching electron‐withdrawing substituents to the carbon atom. While clearly stabilizing in the gas phase, the outcome of this chemical modification in water is more difficult to predict. Herein we provide a definitive and quantitative answer to this question employing a simple strategy based on dynamic combinatorial chemistry. Abstract : Electrostatic and charge‐transfer contributions to CH–π complexes can be modulated by attaching electron‐withdrawing substituents to the carbon atom. Although they have a clearly stabilizing effect in the gas phase, the influence of this chemical modification for the behavior in water is more difficult to predict. Dynamic combinatorial chemistry is used to provide a definitive and quantitative answer to this question.