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Exploiting the Strong Hydrogen Bond Donor Properties of a Borinic Acid Functionality for Fluoride Anion Recognition
Author(s) -
Chen ChangHong,
Gabbaï François P.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201709494
Subject(s) - chemistry , bifunctional , hydrogen bond , fluoride , borane , aqueous solution , ion , polymer chemistry , inorganic chemistry , combinatorial chemistry , organic chemistry , molecule , catalysis
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−F⋅⋅⋅H−O−B hydrogen bond. This hydrogen bond is characterized by a short H‐F distance of 1.79(3) Å and a large coupling constant ( 1 J HF ) of 57.2 Hz. 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.