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Enthalpy of solvation correlations for organic solutes and gases dissolved in dichloromethane and 1,4-dioxane

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Abstract

Enthalpies of solution at infinite dilution of 53 organic solutes in dichloromethane and 10 organic solutes in 1,4-dioxane were measured using semi-adiabatic solution calorimeter. Enthalpies of solvation for 103 organic vapors and gaseous solutes in dichloromethane and for 116 gaseous compounds in 1,4-dioxane were determined from the experimental and literature data. It is shown that an Abraham solvation equation with five descriptors can be used to correlate the experimental solvation enthalpies within standard deviations of 2.07 and 2.29 kJ mol−1 for dichloromethane and 1,4-dioxane, respectively. The derived correlations provide very accurate mathematical descriptions of the measured enthalpy of solvation data at 298 K, which in the case of 1,4-dioxane span a range of 121 kJ mol−1. Division of the experimental values into a training set and a test set shows that there is no bias in predictions, and that the predictive capability of the correlations is better than 3.5 kJ mol−1. Enthalpies of hydrogen bond formation of proton donor solutes (alcohols, amines, chlorinated hydrocarbons, etc.) with 1,4-dioxane were calculated based on the Abraham solvation equation. Obtained values are in good agreement with the available literature data.

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Acknowledgments

Nishu Dabadge and Amy Tian thank the University of North Texas’s Texas Academy of Math and Science (TAMS) program for a summer research fellowship. Mikhail A. Varfolomeev and Ilnaz T. Rakipov acknowledge the financial support by the Russian Federal Program “Scientific and Scientific-Pedagogical Personnel of Innovative Russia 2009–2013” (N P1349).

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Authors and Affiliations

  1. Department of Chemistry, University of North Texas, 1155 Union Circle # 305070, Denton, TX, 76203-5017, USA

    Anastasia Wilson, Amy Tian, Nishu Dabadge & William E. Acree Jr.

  2. Chemical Institute, Kazan Federal University, Kremlevskaya 18, Kazan, 420008, Russia

    Mikhail A. Varfolomeev, Ilnaz T. Rakipov & Svetlana M. Arkhipova

  3. Department of Chemistry, University College London, 20 Gordon Street, London, WC1H 0AJ, UK

    Michael H. Abraham

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  1. Anastasia Wilson
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  2. Amy Tian
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  3. Nishu Dabadge
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Correspondence to William E. Acree Jr..

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This study is honoring Maria Victoria Roux in occasion of her retirement.

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Wilson, A., Tian, A., Dabadge, N. et al. Enthalpy of solvation correlations for organic solutes and gases dissolved in dichloromethane and 1,4-dioxane. Struct Chem 24, 1841–1853 (2013). https://doi.org/10.1007/s11224-013-0233-1

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