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The role of hydrogen bonds in thermodynamic and structural properties in binary mixtures of morpholine + 2-methylcyclohexanol: a combined experimental and computational study

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Abstract

Thermodynamic properties of binary mixtures of 2-methylcyclohexanol with morpholine are measured as a function of composition and temperature. The excess molar volumes were calculated by experimental data. The excess molar volumes are negative over the entire mole fractions. Density functional theory and molecular dynamics (MD) simulation were used to determine the microscopic structure of this mixture in the gas and liquid phases, respectively. In addition, the quantum theory of atoms in molecules was applied to analyze hydrogen-bonding interactions. From MD simulation, density, radial distribution functions, and combined distribution functions of the mixtures with different mole fractions at 298.15 K and 1.0 atm were calculated.

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All data generated or analyzed during this study are included in this published article.

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Acknowledgments

The authors would like to thank the Research Council of Razi University for providing the necessary facilities for performing the research. Cluster computing times, provided in part by the High Performance Computing Research Laboratory of Institute for Research in Fundamental Sciences (IPM), are greatly acknowledged.

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No funds, grants, or other support was received.

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Authors and Affiliations

  1. Faculty of Chemistry, Razi University, P.O. Box 1638, Kermanshah, 6714414971, Iran

    Razieh Mirzaee, Azim Soltanabadi, Sharam Ranjbar & Zahra Fakhri

Authors
  1. Razieh Mirzaee
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  2. Azim Soltanabadi
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  3. Sharam Ranjbar
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  4. Zahra Fakhri
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Contributions

All authors contributed to the study conception and design. A.S., R.M., and S.R. performed material preparation, data collection, and analysis. Z.F. wrote the first draft of the manuscript and all authors commented on previous versions of the manuscript. All authors read and approved the final manuscript.

Corresponding author

Correspondence to Azim Soltanabadi.

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Supporting information

ESM 1.

The Compound Name, CAS Number, Molar Mass, Supplier and Purity of 2‒Methylcyclohexanol and Morpholine, Details force field, thermal expansion coefficient, α, and isothermal coefficient of pressure excess molar enthalpy, \( {\left(\partial {H}_{\mathrm{m}}^{\mathrm{E}}/\partial P\right)}_{T,{x}_1} \), and optimized coordinates are presented in the supplementary material. (DOCX 111 kb)

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Mirzaee, R., Soltanabadi, A., Ranjbar, S. et al. The role of hydrogen bonds in thermodynamic and structural properties in binary mixtures of morpholine + 2-methylcyclohexanol: a combined experimental and computational study. Struct Chem 32, 2319–2332 (2021). https://doi.org/10.1007/s11224-021-01808-9

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  • DOI: https://doi.org/10.1007/s11224-021-01808-9

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