Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 20, Pages 6435-6442Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201204452
Keywords
acylation; nucleophilic catalysis; organocatalysis; structure-activity relationships
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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 structureactivity relationship (QSAR) model is, however, highly predictive.
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