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

  1. Jiménez-Moreno, E. 4
  2. Gõmez, A.M. 4
  3. Bastida, A. 4
  4. Corzana, F. 3
  5. Jiménez-Oses, G. 5
  6. Jiménez-Barbero, J. 126
  7. Asensio, J.L. 4
  1. 1 Centro de Investigaciones Biológicas
    info

    Centro de Investigaciones Biológicas

    Madrid, España

    ROR https://ror.org/04advdf21

  2. 2 CIC-bioGUNE, Derio-Bizkaia, Spain
  3. 3 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  4. 4 Instituto de Química Orgánica General
    info

    Instituto de Química Orgánica General

    Madrid, España

    ROR https://ror.org/05e0q7s59

  5. 5 University of California Los Angeles
    info

    University of California Los Angeles

    Los Ángeles, Estados Unidos

    ROR https://ror.org/046rm7j60

  6. 6 Ikerbasque, Bilbao, Spain
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Revista:
Angewandte Chemie International

ISSN: 1433-7851

Año de publicación: 2015

Volumen: 54

Número: 14

Páginas: 4344-4348

Tipo: Artículo

DOI: 10.1002/ANIE.201411733 PMID: 25664754 SCOPUS: 2-s2.0-84925617392 WoS: WOS:000351679600036 GOOGLE SCHOLAR

Otras publicaciones en: Angewandte Chemie International

Resumen

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. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.