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Fluoride Anion Complexation by a Triptycene-Based Distiborane: Taking Advantage of a Weak but Observable C-H⋅⋅⋅F
Chang-Hong Chen1, François P Gabbaï1
1Department of Chemistry, Texas A&M University, College Station, TX, 77843, USA.
Abstract:
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⋅⋅⋅F hydrogen bond which involves a methine group of the 1,8-triptycenediyl backbone.
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