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Effect of Substituents on the Radical Copolymerization of Ring-Substituted Methyl 2-Cyano-3-Phenyl-2-Propenoates with Styrene

Abstract Copolymerizations of ring-substituted methyl 2-cyano-3-phenyl-2-propenoates, RC6H4CH = C(CN)CO2CH3 (R = C2H5, CH3O, Cl, Br, F) with styrene (M 1) were studied in solution in the presence of a radical initiator. Terminal and penultimate kinetic models were applied for best prediction of the copolymer composition. The Alfrey-Price Q and e parameters calculated for the monomers correlate well with the relative reactivity (1/r 1). The relative reactivity showed a tendency to increase with increasing Hammett constant σ, cyclic voltammetric reduction potential, E p, calculated atomic charge, and 13C-NMR chemical shift on the olefinic α-carbon of the ring-substituted monomers.