A KERR EFFECT STUDY OF CONFORMATIONS OF 1,8-DISUBSITUTED NAPHTHALENES AS SOLUTES

Molar Kerr constants and electric dipole moments are reported for 1,8-diacetylnaphthalene, 1,8-bis(dimethylcarbamoyl)naphthalene, 1-dimethylcarbamoylnaphthalene, 1-dimethylaminonaphthalene, 1-dimethylamino-5-bromonaphthalene, 1-dimethylamino-8-acetylnaphthalene and 1-dimethylamino-8-dimethylcarbamoylnaphthalene as solutes in dioxane at 298 K. The data are analyzed in terms of the preferred solution-state conformations. These data are consistent with the presence in dioxane of acoplanar orientations of substituents to the naphthalene plane. The first and second molecule have substituent orientations almost orthogonal to the naphthalene moiety and the carbonyl groups in anti positions. Preferred conformers of the last two molecules are stabilized due to the Me2N...C = O through-space interaction.