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Strength of Intramolecular Hydrogen Bonding in 2-Biphenylmethanol and 4-Biphenylmethanol

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Abstract

The absolute vapor pressures over the solid and liquid 2-biphenylmethanol and 4-biphenylmethanol were measured using the transpiration method. The standard molar enthalpies of vaporization/sublimation were derived from the temperature dependence of vapor pressures. The standard molar enthalpy of fusion of 2-biphenylmethanol was measured using DSC. The available data on solid-gas, liquid-gas and solid-liquid phase transitions available in the literature have been collected, combined with own experimental results and evaluated using the structure-property relationships and quantum-chemical calculations. The high-level G3MP2 and G4 quantum-chemical methods were used to establish consistency of the experimental and theoretical results. Conformational analysis of 2-biphenylmethanol showed the possible presence of a hydrogen bond between the hydroxyl group and the aromatic ring. The strength of the intramolecular hydrogen bonding in 2-biphenylmethanol and 4-biphenylmethanol was assessed from thermochemistry and quantum-chemical calculations.

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Funding

SPV gratefully acknowledges financial support from the Government of Russian Federation (decree no. 220 of April 9, 2010), agreement no. 14.Z50.31.0038.

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Authors and Affiliations

  1. St. Petersburg State University, 198504, St. Petersburg, Russia

    A. A. Samarov

  2. Department of Physical Chemistry and Faculty of Interdisciplinary Research, Competence Centre CALOR, University of Rostock, 18059, Rostock, Germany

    S. P. Verevkin

  3. Chemical Department, Samara State Technical University, 443001, Samara, Russia

    S. P. Verevkin

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Correspondence to A. A. Samarov or S. P. Verevkin.

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Translated from Zhurnal Obshchei Khimii, 2021, Vol. 91, No. 10, pp. 1499–1510 https://doi.org/10.31857/S0044460X21100048.

To the 90th Anniversary of A.V. Suvorov

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Samarov, A.A., Verevkin, S.P. Strength of Intramolecular Hydrogen Bonding in 2-Biphenylmethanol and 4-Biphenylmethanol. Russ J Gen Chem 91, 1946–1956 (2021). https://doi.org/10.1134/S1070363221100042

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