Relative nucleophilicities of arenesulphonate anions towards methyl trifluoromethanesulphonate in acetonitrile and reactions of the silver salts with methyl iodide

Abstract

Reactions of arenesulphonate anions with an acetonitrile solution of methyl trifluoromethanesulphonate exhibit a negative Hammett ρ value of slightly greater than unity, indicating substantial bonding to the anion within the transition state of the rate-determining step; reactions of the silver salts with methyl iodide exhibit an identical value and a classical S_N2Ag⁺ mechanism is postulated.