Modulating Weak Interactions for Molecular Recognition: A Dynamic Combinatorial Analysis for Assessing the Contribution of Electrostatics to the Stability of CH-π Bonds in Water

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 defin...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-03, Vol.54 (14), p.4344-4348
Main Authors: Jiménez-Moreno, Ester, Gómez, Ana M., Bastida, Agatha, Corzana, Francisco, Jiménez-Oses, Gonzalo, Jiménez-Barbero, Jesús, Asensio, Juan Luis
Format: Article
Language:English
Subjects:
Carbon
CH-π interactions
Combinatorial analysis
Combinatorial chemistry
Combinatorial Chemistry Techniques
drug design
dynamic combinatorial chemistry
Dynamic tests
Dynamics
Electrostatics
Gas phases
Joining
molecular recognition
Static Electricity
Strategy
Water - chemistry
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Summary: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. 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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201411733