ArticleChemistry (Weinheim an der Bergstrasse, Germany)2022
Probing the Lewis Acidity of Boronic Acids through Interactions with Arene Substituents.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
3 citing papers in PubMed.
- Probing Attractive OH-π Interactions and Repulsive n-π Interactions in a Phenol Molecular Balance.Chemistry, an Asian journal · 2026Article
- Adjusting UV-Vis Spectrum of Alizarin by Insertion of Auxochromes.ChemistryOpen · 2024Article
- Probing the Lewis Acidity of Boronic Acids through Interactions with Arene Substituents.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
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Authors and funding
6 authors.
Funding
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.
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