Conformational preferences of the benzenedicarbaldehydes: an ab initio molecular-orbital, dipole-moment and Kerr-effect study

Abstract

Ab initio molecular orbital theory at the STO-3G level is used to elucidate the structures and relative abundances of stable conformations of the three benzenedicarbaldehydes. In addition, new measurements of the infinite-dilution dipole moments and molar Kerr constants of these molecules as solutes in dioxan at 25ºC are reported and analysed. The previously recognized inability of the simple group- additivity model to reliably predict the anisotropy in the polarizability of benzene-1,4-dicarbaldehyde is shown to be due to a redistribution of the polarizability in the molecular plane.