Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 7, Pages 1799-1804Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201611009
Keywords
antimony; fluoride; hydrogen bonds; Lewis acids; molecular recognition
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Funding
- Donors of the American Chemical Society Petroleum Research Fund [56871-ND3]
- Welch Foundation [A1423]
- Texas AM University
- Laboratory for Molecular Simulation at Texas AM University
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Fluoride anion complexation impacts a number of areas ranging from sensing to nucleophilic fluorination chemistry. Described here is a new bidentate Lewis acid consisting of two stiborane units connected by a 1,8-triptycenediyl backbone. This neutral derivative captures fluoride with an unprecedented affinity for a neutral, water-compatible Lewis acid. Structural, spectroscopic and computational studies demonstrate that fluoride anion binding is assisted by the formation of a C-H center dot center dot center dot F hydrogen bond which involves a methine group of the 1,8-triptycenediyl backbone.
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