Conformational analysis of o-allylphenol by density functional and IR spectroscopy methods |
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Authors: | D. V. Berdyshev V. P. Glazunov V. L. Novikov |
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Affiliation: | (1) Chemistry Department, Golestan University, Gorgan, Iran;(2) Pulp and Paper Department, Agricultural and Natural Resources University of Gorgan, Gorgan, Iran |
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Abstract: | The two-dimensional cyclic potential energy surfaces for internal rotation of the allyl substituent and its vinyl fragment in o-allylphenol (o-APh) depending on the OH group orientation relative to the allyl substituent were constructed by a B3LYP/6-31G method. It is shown that o-APh exists in the gas phase as a mixture of eight non-planar rotamers (A, B, C, D, E, F, G, and H) and their eight optical isomers (A 1, B 1, C 1, D 1, E 1, F 1, G 1, and H 1). An intramolecular H-bond (IHB) O–H...π occurs only in four rotamers (A, B, A 1, and B 1). The content of such rotamers in the gas phase is 47.2% (as calculated by the B3LYP/cc-pVTZ method). Taking into account the solvation effect in the polarizable continuum model (PCM) for a solution of o-APh in cyclohexane decreases the total content of rotamers with an IHB (A and B) to 37.7%. The ratio of rotamers with OH groups bonded by an IHB and with free OH groups that is predicted theoretically agrees with the value measured experimentally from IR spectra of o-APH in CCl4 solution. |
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