Quantification of a CH–π Interaction Responsible for Chiral Discrimination and Evaluation of Its Contribution to Enantioselectivity

Authors

  • Romen Carrillo Dr.,

    1. Instituto Universitario de Bio-Orgánica “Antonio González”, Universidad de La Laguna, Francisco Sánchez, 2, 38206 La Laguna, Tenerife (Spain)
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  • Matías López-Rodríguez Prof. Dr.,

    1. Instituto Universitario de Bio-Orgánica “Antonio González”, Universidad de La Laguna, Francisco Sánchez, 2, 38206 La Laguna, Tenerife (Spain)
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  • Victor S. Martín Prof. Dr.,

    1. Instituto Universitario de Bio-Orgánica “Antonio González”, Universidad de La Laguna, Francisco Sánchez, 2, 38206 La Laguna, Tenerife (Spain)
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  • Tomás Martín Dr.

    1. Instituto de Productos Naturales y Agrobiología, CSIC, Francisco Sánchez, 3, 38206 La Laguna, Tenerife (Spain), Fax: (+34) 922-260-135
    2. Instituto Universitario de Bio-Orgánica “Antonio González”, Universidad de La Laguna, Francisco Sánchez, 2, 38206 La Laguna, Tenerife (Spain)
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  • The authors thank Dr. K. Hirose and Dr. J. M. Sanderson for providing the titration isotherm curve fitting program, Dr. Ezequiel Q. Morales for TOC graphic design, and Dr. David Tejedor and Dr. Fernando García-Tellado for helpful discussions. This research was supported by the Spanish MEC (CTQ2005-09074-C02-01 and 02), the MICINN-FEDER (CTQ2008-03334/BQU and CTQ2008-06806-C02-01/BQU), FICIC, the MSC ISCIII (RETICS RD06/0020/1046). R.C. thanks the Spanish MEC for an FPU fellowship.

Abstract

original image

Good things come in small interactions: The high chiral discrimination displayed by a new receptor with ammonium salts of aromatic α-amino acid methyl esters is mainly the result of one of the weakest noncovalent interactions, the CH–π interaction (see picture). The interaction has been identified and quantified, and its contribution to the chiral recognition process has been evaluated.

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