A series of alkyl alpha-hydroxymethacrylate derivatives with various secondary functionalities (ether, ester, carbonate, and carbamate) and terminal groups (alkyl, cyano, oxetane, cyclic carbonate, phenyl and morpholine) were synthesized to investigate the effect of intermolecular interactions, H-bonding, pi-pi interactions, and dipole moment on monomer reactivity. All of the monomers except one ester and one ether derivative are novel. The polymerization rates, determined by using photo-DSC, showed the average trend (aromatic carbamate > hydroxyl > ester > carbonate similar to aliphatic carbamate similar to ether), with several exceptions due to the differences in terminal groups. There is a correlation between the chemical shift differences of the double bond carbons, the calculated dipole moments, and the reactivities only for nonhydrogen bondedmonomers. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 3058-3068, 2011