RELATIVE NUCLEOPHILICITY . METHYLATION OF ANIONS IN AQUEOUS MEDIA

Alkylation rate data were obtained for 16 anion nucleophiles in aqueous media at 25° (and 37°) and constant salt concentration using 1-methyl-3-(methylsulfonate)pyridinium perchlorate as the alkylating agent substrate. The data at 25° are presented in terms of log K2/Kw and the Swain and Scott equation is employed to obtain the substrate constant, s (0.715). Nucleophilic constants, n, are calculated and compared with published values for 12 anions, and new constants were determined for four phosphonate ion species. © 1969, American Chemical Society. All rights reserved.