Trioxatriangulenium (TOTA⁺) as a robust carbon-based Lewis acid in frustrated Lewis pair chemistry.

ABSTRACT: We report the reactivity between the water stable Lewis acidic trioxatriangulenium ion (TOTA⁺) and a series of Lewis bases such as phosphines and N-heterocyclic carbene (NHC). The nature of the Lewis acid-base interaction was analyzed via variable temperature (VT) NMR spectroscopy, single-crystal X-ray diffraction, UV-visible spectroscopy, and DFT calculations. While small and strongly nucleophilic phosphines, such as PMe₃, led to the formation of a Lewis acid-base adduct, frustrated Lewis pairs (FLPs) were observed for sterically hindered bases such as P( ^t Bu)₃. The TOTA⁺-P( ^t Bu)₃ FLP was characterized as an encounter complex, and found to promote the heterolytic cleavage of disulfide bonds

SUBMITTER: Shaikh AC 

PROVIDER: S-EPMC8179643 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature