Exploiting the Strong Hydrogen Bond Donor Properties of a Borinic Acid Functionality for Fluoride Anion Recognition |
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| Authors: | Chang‐Hong Chen Prof. Dr. François P. Gabbaï |
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| Affiliation: | 1. http://www.chem.tamu.edu/rgroup/gabbai/;2. Department of Chemistry, Texas A&M University, College Station, TX, USA |
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| 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 (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. |
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| Keywords: | boron fluoride hydrogen bonds molecular recognition sensors |
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