ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Theoretical-study of the rotational barrier height of the anisole molecule for different solvents and partition-coefficients solvent water

L. Turi Nagy and M. Jančárova

Institute of Experimental Pharmacology, Centre for Physiological Sciences, Slovak Academy of Sciences, CS-842 16 Bratislava

Abstract: The height of the rotational barrier of anisole molecule (methoxybenzene) has been studied for 20 different environments, including vacuum, using the continuum reaction field method in connection with a quantum-chemical calculation. The energy of the isolated molecule was calculated by the PCILO method. Before the anisole molecule energy calculation in particular solvents, two models of anisole and phenol hybridization were tested in vacuo and the influence of the hybridization on their conformation was investigated. It has been found that the resulting conformations do not depend on the type of oxygen atom hybridization used. However, the О atom hybridization influen­ ces the energy shift of the whole conformational map. It has also been found that the way of including solvent effect used gives the right trend of the partition coefficients of anisole, despite the fact that the values of the partition coefficients systematically differ from those resulting from the experiment. However, the way of including solvent effect has failed to predict the height of the rotational barrier in various environments.

Full paper in Portable Document Format: 393a289.pdf

Chemical Papers 39 (3) 289–294 (1985)