Probing the Lewis Acidity of Boronic Acids through Interactions with Arene Substituents

Jie Jian, Roel Hammink, Christine J McKenzie, F Matthias Bickelhaupt, Jordi Poater*, Jasmin Mecinović*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

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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.

Original languageEnglish
Article numbere202104044
JournalChemistry - A European Journal
Volume28
Issue number9
Number of pages7
ISSN1521-3765
DOIs
Publication statusPublished - 16. Feb 2022

Keywords

  • Boronic Acids/chemistry
  • Lewis Acids
  • Proteins/chemistry

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