Merging Electron Deficient Boronic Centers with Electron-Withdrawing Fluorine Substituents Results in Unique Properties of Fluorinated Phenylboronic Compounds

Fluorinated boron species are a very important group of organoboron compounds used first of all as receptors of important bioanalytes, as well as biologically active substances, including Tavaborole as an antifungal drug. The presence of substituents containing fluorine atoms increases the acidity of boronic compounds, which is crucial from the point of view of their interactions with analytes or certain pathogen's enzymes. The review discusses the electron acceptor properties of fluorinated boronic species using both the acidity constant (pK(a)) and acceptor number (AN) in connection with their structural parameters. The NMR spectroscopic data are also presented, with particular emphasis on F-19 resonance due to the wide range of information that can be obtained from this technique. Equilibria in solutions, such as the dehydration of boronic acid to form boroxines and their esterification or cyclization with the formation of 3-hydroxyl benzoxaboroles, are discussed. The results of the latest research on the biological activity of boronic compounds by experimental in vitro methods and theoretical calculations using docking studies are also discussed.

Automated summary

Fluorinated boron species are important organoboron compounds used in bioanalysis and antifungal drugs. The presence of fluorine substituents increases the acidity of boronic compounds, which is crucial for their interactions with bioanalytes and pathogen enzymes. This review discusses the electron acceptor properties, NMR spectroscopy data, and solution equilibria of fluorinated boronic species, as well as the latest research on their biological activity.