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Accessing Frustrated Lewis Pair Chemistry from a Spectroscopically Stable and Classical Lewis Acid‐Base Adduct
Author(s) -
Johnstone Timothy C.,
Wee Gabriel N. J. H.,
Stephan Douglas W.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201802385
Subject(s) - lewis acids and bases , adduct , frustrated lewis pair , chemistry , reactivity (psychology) , dissociation (chemistry) , stereochemistry , base (topology) , medicinal chemistry , catalysis , organic chemistry , medicine , mathematical analysis , alternative medicine , mathematics , pathology
B(C 6 F 5 ) 3 and P(MeNCH 2 CH 2 ) 3 N form a classical Lewis adduct, (C 6 F 5 ) 3 BP(MeNCH 2 CH 2 ) 3 N. Although (C 6 F 5 ) 3 BP(MeNCH 2 CH 2 ) 3 N does not exhibit spectroscopic evidence of dissociation into its constituent acid and base, products of frustrated Lewis pair (FLP) addition reactions are seen with PhNCO, PhCH 2 N 3 , PhNSO, and CO 2 . Computational studies show that thermal access to the dissociated acid and base permits FLP reactivity to proceed. These results demonstrate that FLP reactivity extends across the entire continuum of equilibria governing Lewis acid‐base adducts.