Effect of the nature of the nucleophile and solvent on an SNAr reaction

The reaction of 2,4-dinitrobenzenesulfonyl chloride toward propylamine was kinetically evaluated in 19 organic solvents and 10 ionic liquids as reaction media. This study was compared with a previous study to experimentally show that solvent effects and the nature of the reacting pair drastically affect the reaction rate and the reaction mechanism. While the reaction of the reference electrophile 2,4-dinitrobenzenesulfonyl chloride with piperidine is favored in polar solvents with the ability to donate or accept hydrogen bonds, the reaction with propylamine is favored in solvents with the ability to accept hydrogen bonds.