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- Title
Exploiting the Strong Hydrogen Bond Donor Properties of a Borinic Acid Functionality for Fluoride Anion Recognition.
- Authors
Chen, Chang‐Hong; Gabbaï, François P.
- Abstract
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 JHF) 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.
- Subjects
HYDROGEN bonding; BORINIC acids; FLUORIDES; ANIONS; MOLECULAR recognition
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 2, p530
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201709494