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Brønsted Acid Catalysis: Hydrogen Bonding versus Ion Pairing in Imine Activation
Author(s) -
Fleischmann Matthias,
Drettwan Diana,
Sugiono Erli,
Rueping Magnus,
Gschwind Ruth M.
Publication year - 2011
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.201101385
Subject(s) - pairing , imine , catalysis , hydrogen bond , hydrogen , chemistry , combinatorial chemistry , spectroscopy , molecule , organic chemistry , physics , superconductivity , quantum mechanics
Behind the scenes : NMR spectroscopy was used to distinguish hydrogen bonding and ion pairing in the activation of imines by a phosphate catalyst (see structures). Hydrogen‐bond strength and the amount of the hydrogen‐bonded species present are decisive for the catalytic reaction and can be manipulated by introducing substituents with different electronic properties. This insight should guide the development of more efficient catalytic systems.