CONFORMATIONAL INVESTIGATION OF 1,8-DISUBSTITUTED NAPHTHALENES AS SOLUTES BY KERR-EFFECT AND DIPOLE-MOMENT METHODS

Molar Kerr constants and electric dipole moments are reported for 1-methoxycarbonylnaphthalene, 1-bromo-5-methoxycarbonylnaphthalene, 1-bromo-5-nitronaphthalene, 1-amino-8-bromonaphthalene, 1-dimethylamino-8-methoxycarbonylnaphthalene and 1-dimethylamino-8-dimethylthiocarbamoylnaphthalene as solutes in dioxane at 298 K. The data are analyzed in terms of the preferred conformations in solution. These data are consistent with acoplanar orientations of 1- and 1,8-substituents relative to the naphthalene plane. The preferred conformers of the last two molecules are stabilized by a Me2N...C=O(S) through-space interaction.