Peculiarities of the effects of trifluoromethyl and alkoxycarbonyl groups on the structure and reactivity of acrylates 1. Monosubstituted acrylates

Ab initio quantum-chemical calculations of molecules of CF3-substituted acr ylates and their non-fluorinated analogs were carried out by the restricted Hartree-Fock (RHF) method and at the second-order Moller-Plesset (MP2) lev el of perturbation theory using the 6-31G* basis set with full geometry opt imization. Peculiarities of their molecular and electronic structure were r evealed and the dipole moments, the polarizability and first molecular hype rpolarizability tensors, harmonic vibrational frequencies, electrostatic po tentials, and local electron densities in the vicinity of the carbon atoms of the C=C bond were calculated. It was shown that CF3-substituted acrylate s are conjugated systems similar to their nonfluorinated analogs. Peculiari ties of the structure and properties of CF3-substituted acrylates are expla ined by p-pi-interaction between the CF3 group and the conjugated system.