Peculiarities of the effects of trifluoromethyl and alkoxycarbonyl groups on the structure and reactivity of acrylates

Ab initio quantum-chemical calculations of molecules of CF₃-substituted acrylates and their non-fluorinated analogs were carried out by the restricted Hartree-Fock (RHF) method and at the second-order Møller-Plesset (MP2) level of perturbation theory using the 6–31G^* basis set with full geometry optimization. Peculiarities of their molecular and electronic structure were revealed and the dipole moments, the polarizability and first molecular hyperpolarizability tensors, harmonic vibrational frequencies, electrostatic potentials, and local electron densities in the vicinity of the carbon atoms of the C=C bond were calculated. It was shown that CF₃-substituted acrylates are conjugated systems similar to their nonfluorinated analogs. Peculiarities of the structure and properties of CF₃-substituted acrylates are explained by p-π-interaction between the CF₃ group and the conjugated system.