Issue 6, 2014

Mechanistic pathways of aromatic nucleophilic substitution in conventional solvents and ionic liquids

Abstract

Solvation effects on the reaction mechanism of the title reactions have been kinetically evaluated in 21 conventional solvents and 17 ionic liquids. Solvent polarity affects the catalyzed and non-catalyzed SNAr pathways differently. The ambiphilic character of water and formamide, which act as a hydrogen bond donor/acceptor, induces nucleophilic activation at the nitrogen center of the nucleophile. The ionic liquid EMIMDCN appears to be the best solvent for the SNAr route probably due to the high polarizability of the dicyanamide anion.

Graphical abstract: Mechanistic pathways of aromatic nucleophilic substitution in conventional solvents and ionic liquids

Supplementary files

Article information

Article type
Paper
Submitted
24 Jan 2014
Accepted
12 Mar 2014
First published
14 Mar 2014

New J. Chem., 2014,38, 2611-2618

Author version available

Mechanistic pathways of aromatic nucleophilic substitution in conventional solvents and ionic liquids

M. Gazitúa, R. A. Tapia, R. Contreras and P. R. Campodónico, New J. Chem., 2014, 38, 2611 DOI: 10.1039/C4NJ00130C

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