Abstract
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
Graphical Abstract
Nucleophilic Reactivities of Schiff Bases
Received: 2013-03-08
Published Online: 2014-06-02
Published in Print: 2013-06-01
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