Premium
Annelated Pyridines as Highly Nucleophilic and Lewis Basic Catalysts for Acylation Reactions
Author(s) -
Tandon Raman,
Unzner Teresa,
Nigst Tobias A.,
De Rycke Nicolas,
Mayer Peter,
Wendt Bernd,
David Olivier R. P.,
Zipse Hendrik
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201204452
Subject(s) - nucleophile , lewis acids and bases , chemistry , acylation , catalysis , affinities , computational chemistry , organic chemistry , medicinal chemistry , stereochemistry
New heterocyclic derivatives of 9‐azajulolidine have been synthesized and characterized with respect to their nucleophilicity and Lewis basicity. The Lewis basicity of these bases as quantified through their theoretically calculated methyl‐cation affinities correlate well with the experimentally measured reaction rates for addition to benzhydryl cations. All newly synthesized pyridines show exceptional catalytic activities in benchmark acylation reactions, which correlate only poorly with Lewis basicity or nucleophilicity parameters. A combination of Lewis basicity with charge and geometric parameters in the framework of a three‐component quantitative structure–activity relationship (QSAR) model is, however, highly predictive.