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Conformational analysis and interpretation of ν(OH) band in the IR spectrum of o-vinylphenol: a DFT study

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Abstract

Two-dimensional cyclic potential energy surface for internal rotation of vinyl and hydroxyl substituents in o-vinylphenol molecule was constructed by the B3LYP/6-311G(d) method. It was shown that o-vinylphenol molecule exists in the gas phase as a mixture of seven rotamers denoted as A (A′), B (B′), C (C′) and D. The B3LYP/cc-pVTZ calculated percentage of the rotamers A and A′ in which OH…π intramolecular interaction occurs, is at most 24%. The height of barriers t interconversions between o-vinylphenol rotamers varies from 0.1 to 5.2 kcal mol−1. According to B3LYP/cc-pVTZ calculations, the inclusion of solvent effect in the framework of the polarizable continuum model for a solution of o-vinylphenol in CCl4 leads to a decrease in theoretical values of ν(OH) frequencies by about 4–9 cm−1 and to an increase in the percentage of the rotamers without intramolecular hydrogen bond by about 4.3% compared to the corresponding gas-phase values. The simulated IR spectral contours of ν(OH) bands are in good agreement with experimental one

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Authors and Affiliations

  1. Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, 159 Prospekt 100-letiya Vladivostoka, 690022, Vladivostok, Russian Federation

    D. V. Berdyshev, V. P. Glazunov & V. L. Novikov

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  1. D. V. Berdyshev
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  2. V. P. Glazunov
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  3. V. L. Novikov
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Correspondence to D. V. Berdyshev.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 499–508, March, 2008.

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Berdyshev, D.V., Glazunov, V.P. & Novikov, V.L. Conformational analysis and interpretation of ν(OH) band in the IR spectrum of o-vinylphenol: a DFT study. Russ Chem Bull 57, 510–519 (2008). https://doi.org/10.1007/s11172-008-0079-7

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  • DOI: https://doi.org/10.1007/s11172-008-0079-7

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