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

Gazitua M.; Tapia, R.A.; Contreras R.; Campodónico, P. R.

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.

Más información

Título según WOS: Mechanistic pathways of aromatic nucleophilic substitution in conventional solvents and ionic liquids
Título según SCOPUS: Mechanistic pathways of aromatic nucleophilic substitution in conventional solvents and ionic liquids
Título de la Revista: NEW JOURNAL OF CHEMISTRY
Volumen: 38
Número: 6
Editorial: ROYAL SOC CHEMISTRY
Fecha de publicación: 2014
Página de inicio: 2611
Página final: 2618
Idioma: English
DOI:

10.1039/c4nj00130c

Notas: ISI, SCOPUS - ISI