A multinuclear NMR perspective on the complexation between bisboronic acids and bisbenzoxaboroles with cis -diols

Autor: Danielle Laurencin, Michael Smietana, Aurélien Lebrun, Adèle Larcher
Přispěvatelé: Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)
Jazyk: angličtina
Rok vydání: 2018
Předmět:
Zdroj: New Journal of Chemistry
New Journal of Chemistry, Royal Society of Chemistry, 2018, 42 (4), pp.2815-2823. ⟨10.1039/C7NJ04143H⟩
ISSN: 1144-0546
1369-9261
Popis: The interaction between boronic acids and cis-diols is an intense area of research, with numerous applications in sensing, separation, drug delivery, and materials science. Several analytical tools have been proposed over the past 20 years to probe these interactions, but most of them are limited by shortcomings such as high concentration requirements and/or the lack of clear evidence of the nature of the species present in solution. These drawbacks are all the more problematic in the case of compounds bearing multiple binding sites. In this work, a multinuclear (1H, 11B, 19F) NMR spectroscopy approach has been used to investigate for the first time the equilibria between bisboronic acids and bisbenzoxaboroles (as well as their monofunctional counterparts) with representative cis-diols, including catechol derivatives. The developed method is shown to provide valuable and straightforward insight into the nature of the species in solution, and the way in which the equilibria can be affected by the complexation media. In particular, the interest of using a 19F-tag on the cis-diol is emphasized.
Databáze: OpenAIRE