Benzylidene fluorene ozonolysis under chemiluminescence mimetic conditions in homogeneous and micellar media III: Substituent effect in the micellar pseudophase

Abstract

The binding constants, mean occupation numbers per micelle, partition coefficients and per cent micellization of nine 9-(p-substituted) benzylidene fluorenes (p-nitro (i); p-cyano (ii); p-chloro (iii); p-bromo (iv); p-H (v); p-methyl (vi); p-methoxy (vii); p-methoxy-m-methyl (viii); p-dimethylamino (ix)) in cetyltrimethylammonium chloride and sodium dodecylsulphate were determined from the corresponding Stern—Volmer plots, with pyrene as the fluorescent probe. The ozonolysis reaction rates of the nine benzylidene fluorenes were measured in the micellar systems and, from the above partition coefficients together with the reaction rates in the bulk phase, the reaction rates in the micellar pseudophase, independent of the reaction rate in the bulk phase and the partition coefficient, were determined; the plots of these reaction rates (log k_tr or log k_app) against Hammett's σ constants were linear.