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Z. Naturforsch. 2013,
68b, 693 – 699
doi:10.5560/ZNB.2013-3085
Nucleophilic Reactivities of Schiff Bases
Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5–13 (Haus F), 81377 München, Germany
Reprint requests to Prof. Dr. H. Mayr. Fax: +49 89 2180 77717. E-mail:
Herbert.Mayr@cup.uni-muenchen.de
Received March 8, 2013 / published online Juli 2, 2013
Dedicated to Professor Heinrich Nöth on the occasion of his 85th birthday
The nucleophile-specific parameters N and sN, as defined by the linear free energy relationship log k = sN(N + E) (J. Am. Chem. Soc. 2001, 123, 9500–9512), were determined for five imines 1a–e by studying the kinetics of their reactions with benzhydrylium ions in dichloromethane solution at 20 °C. These parameters allowed us to include representative Schiff bases into our comprehensive nucleophilicity scale and compare their reactivities with those of other N-nucleophiles.
Key words: Kinetics, Linear Free Energy Relationship, Imine, Azomethine, Carbenium Ions