Exploiting the Strong Hydrogen Bond Donor Properties of a Borinic Acid Functionality for Fluoride Anion Recognition. Academic Article uri icon


  • Borinic acids have typically not been considered as hydrogen bond donor groups in molecular recognition. Described herein is a bifunctional borane/borinic acid derivative (2) in which the two functionalities are connected by a 1,8-biphenylenediyl backbone. Anion binding studies reveal that 2 readily binds a fluoride anion by formation of a unique B-FH-O-B hydrogen bond. This hydrogen bond is characterized by a short H-F distance of 1.79(3) and a large coupling constant (1 JHF ) of 57.2Hz. The magnitude of this interaction, which has also been investigated computationally, augments the fluoride anion binding properties of 2, thus making it compatible with aqueous environments.

published proceedings

  • Angew Chem Int Ed Engl

altmetric score

  • 7.75

author list (cited authors)

  • Chen, C., & Gabbai, F. P.

citation count

  • 33

complete list of authors

  • Chen, Chang-Hong||Gabbaiï, François P

publication date

  • January 2018