Use of semiempirical quantum chemical approaches in computation of molecular dipole moments of tropones and tropolones

Alexei Pankratov
2000 Journal of the Serbian Chemical Society  
Using the MNDO, AM1 and PM3 methods, the dipole moments (m) of 28 tropones and 34 tropolones molecules have been computed. The potentials of the above approaches for the evaluation of m have been revealed. The correlations mANFAH = >mtheor have been established. The tropones and tropolones are intriguing series of compounds '! combining the properties of non-benzenoid aromatic and unsaturated compounds. In some instances tropone manifests itself as a ketone, while tropolone behaves as a vinylog
more » ... of a carboxyl. Tropolone derivatives are found in wood and essential oils of the +OFHAII family of plants. They exhibit an antimitotic effect, possess bacteriostatic, bactericidal and antifungal activity, and serve as antibiotics, 4,6,8,1316 . The tropolones are possible intermediates of alkaloids biogenesis. 6,8,12,13 Liquid crystals, ionophores, J-aggregated dyes and other advanced materials based on troponoids are known. % Molecular recognition and bioactive compound interaction with biosubstrates receptors are preceded by chemical substance selection in accordance with the electrostatic mechanism. &' An important characteristic of the electric properties of a molecule and a measure of its electrostatic (ion-dipole, dipole-dipole) interaction with other molecular systems is its dipole moment. Along with the elucidation of biological effects, information on the dipole moments is required when considering the mutual influence of atoms, the electronic effects in molecules, intermolecular interactions, hydrogen bonds, tautomeric conversions, solvation and when solving other chemical and physicochemical problems. 22,23
doi:10.2298/jsc0001001p fatcat:djhsbaonrreyhbtetyiipqpqmi