Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 28, Issue 9, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202104044
Keywords
aromatic compounds; boronic acids; Lewis acidity; non-covalent interactions; polar-pi interactions
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Funding
- China Scholarship Council [CSC201808440511]
- Netherlands Organization for Scientific Research (NWO)
- Spanish MINECO [PID-2019-106830GB-I00, MDM-2017-0767]
- Generalitat de Catalunya [2017SGR348]
- Carlsberg Foundation [CF15-0675]
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This study experimentally and computationally investigates the Lewis acidity of 2,6-diarylphenylboronic acids. The research suggests that polar-pi interactions and solvation effects contribute to the stabilization of boronic acids and boronate forms by aromatic rings.
Boronic acids are Lewis acids that exist in equilibrium with boronate forms in aqueous solution. Here we experimentally and computationally investigated the Lewis acidity of 2,6-diarylphenylboronic acids; specially designed phenylboronic acids that possess two flanking aromatic rings with tunable aromatic character. Hammett analysis of 2,6-diarylphenylboronic acids reveals that their Lewis acidity remains unchanged upon the introduction of EWG/EDG at the distant para position of the flanking aromatic rings. Structural and computational studies demonstrate that polar-pi interactions and solvation effects contribute to the stabilization of boronic acids and boronate forms by aromatic rings. Our physical-organic chemistry work highlights that boronic acids and boronates can be stabilized by aromatic systems, leading to an important molecular knowledge for rational design and development of boronic acid-based catalysts and inhibitors of biomedically important proteins.
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