title: Annelated pyridines as highly nucleophilic and Lewis basic catalysts for acylation reactions.
abstract: 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.
authors.affiliation: Department of Chemistry, LMU München, Butenandtsrasse 5-13, 81377 München, Germany.
authors.forename: Raman
authors.initials: R
authors.lastname: Tandon
authors.forename: Teresa
authors.initials: T
authors.lastname: Unzner
authors.forename: Tobias A
authors.initials: TA
authors.lastname: Nigst
authors.forename: Nicolas
authors.initials: N
authors.lastname: De Rycke
authors.forename: Peter
authors.initials: P
authors.lastname: Mayer
authors.forename: Bernd
authors.initials: B
authors.lastname: Wendt
authors.forename: Olivier R P
authors.initials: OR
authors.lastname: David
authors.forename: Hendrik
authors.initials: H
authors.lastname: Zipse