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Physicochemical Properties, 1H-NMR, Ab Initio Calculations and Molecular Interaction in Binary Mixtures of N-methylimidazole with Methanol

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Abstract

Over the full molar fraction range, the density, viscosity, refractive index, conductivity and pH at the temperatures (298.15, 308.15, and 318.15) K, mixing enthalpy at T = 298.15 K, and 1H-NMR were measured for the binary mixtures of x N-methylimidazole (hereafter abbreviated to N-mim) + (1 − x) methanol, together with ab initio calculations. The thermodynamic parameters of activation for viscous flow were calculated and analyzed. The excess molar volume, viscosity deviation, deviation for the logarithm of viscosity, refractive index deviation and the excess refractive index, excess Gibbs energy of activation of viscous flow and the molar mixing enthalpy were calculated and fitted with a Redlich–Kister equation. The partial molar mixing enthalpies and the protons’ chemical shift changes of N-mim and methanol were calculated and explained. An increase in temperature leads to the excess molar volume becoming more negative, whereas the deviations for the logarithm of viscosity, viscosity deviation and the excess Gibbs energy of activation of viscous flow become less positive; in contrast the refractive index deviation and the excess refractive index become less positive at first and then become more positive. The activation of the viscous fluid is a more ordered process. The physicochemical properties, ab initio calculations, combined with the 1H-NMR results reveal that the molecular interactions among unlike molecules is stronger than that between like ones. There is an ionization process and hydrogen bond interaction between N-mim and methanol, the predominant interaction is N-mim:methanol = 1:1 hydrogen-bonded network, where the methyl groups of methanol and N-mim, respectively, are electron-withdrawing and electron-donating groups.

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Acknowledgements

The authors are grateful to the National Natural Science Foundation of China (No. 21603169), Scientific Research Fund of the Science and Technology Department of Shaanxi Provincial Government (No. 2016JM5049), and the College Students innovation Project (No. 201610709028) for financial supports, and are grateful to Dr. Baojian Liu for his assistance in the NMR measurements.

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  1. College of Environmental and Chemical Engineering, Xi’an Polytechnic University, Xi’an, 710048, Shaanxi, China

    Haiyun Hou, Xinlu Lin & Songtao Liu

  2. School of Chemical Engineering, Xi’an University, Xi’an, 710065, China

    Baojuan Jiao

  3. Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Yantai University, Yantai, 264005, China

    Qingzhong Li

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Hou, H., Jiao, B., Li, Q. et al. Physicochemical Properties, 1H-NMR, Ab Initio Calculations and Molecular Interaction in Binary Mixtures of N-methylimidazole with Methanol. J Solution Chem 47, 1875–1901 (2018). https://doi.org/10.1007/s10953-018-0824-y

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