Optical activity in βγ-unsaturated ketones. Part 2. Effect of the magnitude and energy of the electric transition dipole moment in the aromatic groups in 1- and 1,5-substituted 9,10-ethano-9,10-dihydroanthracen-11-one derivatives

Abstract

In 1- or 1,5-substituted 9,10-ethano-9,10-dihydroanthracen-11-one derivatives, the alteration of the substituents on the benzene ring brings about a change of the magnitude of the transition dipole moment and the transition energy in the aromatic chromophore without much alteration of the direction of the transition dipole moment. We synthesized optically active derivatives of the title compounds, determined their absolute configuration, studied the effects on the optical activity, and analysed them by application of dynamic and static coupling mechanisms. The optical activity was found to depend mainly on the magnitude of the transition dipole moment.