Exploiting the Strong Hydrogen Bond Donor Properties of a Borinic Acid Functionality for Fluoride Anion Recognition

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...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-01, Vol.57 (2), p.521-525
Main Authors: Chen, Chang‐Hong, Gabbaï, François P.
Format: Article
Language:English
Subjects:
Acids
Anions
Aqueous environments
Binding
boron
Coupling (molecular)
fluoride
Fluorides
Hydrogen
Hydrogen bonds
molecular recognition
Recognition
sensors
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Summary: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 (1JHF) 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. A Brønsted and Lewis handshake: The borinic acid functionality of a new diboron electrophilic host reaches across the binding pocket to engage a borane‐bound fluoride anion in a strong hydrogen‐bonding interaction. The resulting B−F⋅⋅⋅H−O−B interaction stabilizes the complex in aqueous solutions, thereby illustrating the role that borinic acids may play as hydrogen bond donor groups.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201709494