The nature of smectic A liquid crystals and the phase transitions from smectic A to nematic phases are studied in the homologous series of 4-(4″-octyloxy-benzoyloxy)benzylidene-4′-substituted anilines, in which the substituents are H, F, Cl, Br, I, NO2and CN. Measurements have been performed for the dipole moment of the molecule, the smectic A lattice period, the temperatures and the entropies of phase transitions, and the temperature dependence of the orientational order parameter, all of which provide information on the intermolecular pair potentials. It is shown that the introduction of a terminal polar substituent brings about counteracting contributions to the stability of the smectic A state. It is suggested that the reentrant nematic phase transition can appear in the strongly polar mesogens if the extent of antiparallel association of the molecules increases on lowering the temperature.