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Energetics of substituent effects on the benzene ring: CH3O with F, Cl, Br, and I

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Abstract

The temperature dependences of vapour pressures for some mono- and di-halogenated anisoles were established using the transpiration method. The solution calorimetry-based approach was used to determine the vaporization/sublimation enthalpies of chlorine- and iodine-substituted anisoles. The enthalpies of fusion of 2,3-di-chloro-anisole and 4-iodo-anisole were measured using differential scanning calorimetry. The literature thermochemical data for halogen-substituted anisoles (with halogen = F, Cl, Br, and I) and new results were evaluated using “structure–property” correlations and quantum-chemical calculations. The G* quantum chemical methods were validated for reliable estimation of the enthalpies of formation of substituted for halogen-substituted anisoles in the gaseous state. The evaluated thermodynamic data were used for designing the “centrepiece” method for assessment of enthalpies of vaporization and enthalpies of formation for halogen-substituted anisoles.

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Acknowledgements

This paper has been supported by the Kazan Federal University Strategic Academic Leadership Program (‘PRIORITY-2030’).

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Authors and Affiliations

  1. Department of Physical Chemistry, Kazan Federal University, 420008, Kazan, Russia

    Ruslan N. Nagrimanov, Aliya R. Ibragimova, Almaz R. Italmasov, Dmitry A. Kornilov, Marat A. Ziganshin, Boris N. Solomonov & Sergey P. Verevkin

  2. Department of Physical Chemistry, University of Rostock, 18059, Rostock, Germany

    Sergey P. Verevkin

  3. Competence Centre CALOR, Faculty of Interdisciplinary Research, University of Rostock, 18059, Rostock, Germany

    Sergey P. Verevkin

  4. Department of Physical Chemistry and Chemical Ecology, Bashkir State University, 450076, Ufa, Russia

    Dmitry A. Kornilov

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  1. Ruslan N. Nagrimanov
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  2. Aliya R. Ibragimova
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Contributions

RNN: Conceptualization, Methodology, Writing—Original draft preparation, Supervision. ARI: Writing—original draft, Investigation. ARI: Writing—original draft, Investigation. DAK: Writing—original draft, Investigation. MAZ: Writing—original draft, Investigation. BNS: Methodology. SPV: Conceptualization, Methodology, Writing—Original draft preparation, Supervision.

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Correspondence to Ruslan N. Nagrimanov or Sergey P. Verevkin.

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Nagrimanov, R.N., Ibragimova, A.R., Italmasov, A.R. et al. Energetics of substituent effects on the benzene ring: CH3O with F, Cl, Br, and I. J Therm Anal Calorim 148, 1087–1108 (2023). https://doi.org/10.1007/s10973-022-11673-1

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