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 ba...
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.
Ringübergreifende Kooperation: Die Borinsäurefunktion überbrückt die Bindetasche einer diborierten elektrophilen Wirtspezies, um mit einem Boran‐gebundenen Fluorid‐Anion eine starke Wasserstoffbrücke einzugehen. Die B‐F⋅⋅⋅H‐O‐B‐Wechselwirkung stabilisiert den Komplex in wässrigen Lösungen, was das Potenzial von Borinsäuren als Wasserstoffbrückendonoren belegt.