Exploring structural and electronic effects in three isomers of tris{bis(trifluoromethyl)phenyl}borane: Towards the combined electrochemical-frustrated Lewis pair activation of H2

Robin J. Blagg, Elliot J. Lawrence, Katie Resner, Vasily S. Oganesyan, Thomas J. Herrington, Andrew E. Ashley, Gregory G. Wildgoose

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Abstract

Three structural isomers of tris{bis(trifluoromethyl)phenyl}borane have been studied as the acidic com- ponent of frustrated Lewis pairs. While the 3,5-substituted isomer is already known to heterolytically cleave H2 to generate a bridging-hydride; ortho-substituents in the 2,4- and 2,5-isomers quench such reactivity through electron donation into the vacant boron pz orbital and steric blocking of the boron centre; as shown by electrochemical, structural and computational studies. Electrochemical studies of the corresponding borohydrides identify that the two-electron oxidation of terminal-hydrides occurs at more positive potentials than observed for [HB(C6F5)3]−, while the bridging-hydride oxidizes at a higher poten- tial still, comparable to that of free H2.
Original languageEnglish
Pages (from-to)6023-6031
JournalDalton Transactions
Volume45
Issue number14
Early online date28 Jul 2015
DOIs
Publication statusPublished - 14 Apr 2016

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