Author:

Keywords:

aromatic compounds, AROMATIC RINGS, boronic acids, Chemistry, CHEMISTRY, Chemistry, Multidisciplinary, Lewis acidity, non-covalent interactions, Physical Sciences, polar-pi interactions, PROTODEBORONATION, Science & Technology, polar-π interactions, Boronic Acids, Lewis Acids, Proteins, 03 Chemical Sciences, General Chemistry, 34 Chemical sciences

Abstract:

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-π 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.