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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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References

  1. Liu, J., Wang, Z., Levin, A., Emge, T.J., Rablen, P.R., Floyd, D.M., Knapp, S.: N-Methylimidazole promotes the reaction of homophthalic anhydride with imines. J. Org. Chem. 79, 7593–7599 (2014)

    Article  CAS  Google Scholar 

  2. Yoganathan, S., Miller, S.J.: N-Methylimidazole-catalyzed synthesis of carbamates from hydroxamic acids via the Lossen rearrangement. Org. Lett. 15, 602–605 (2013)

    Article  CAS  Google Scholar 

  3. Xu, A., Wang, J., Zhang, Y., Chen, Q.: Effect of alkyl chain length in anions on thermodynamic and surface properties of 1-butyl-3-methylimidazolium carboxylate ionic liquids. Ind. Eng. Chem. Res. 51, 3458–3465 (2012)

    Article  CAS  Google Scholar 

  4. Yang, J.Z., Zhang, Q.G., Wang, B., Tong, J.: Study on the properties of smino acid ionic liquid EMIGly study on the properties of amino acid ionic liquid EMIGly. J. Phys. Chem. B 110, 22521–22524 (2006)

    Article  CAS  Google Scholar 

  5. Ding, Z.D., Chi, Z., Gu, W.X., Gu, S.M., Wang, H.J.: Theoretical and experimental investigation of the interactions between [Emim]Ac and water molecules. J. Mol. Struct. 1015, 147–155 (2012)

    Article  CAS  Google Scholar 

  6. Ma, X.X., Wei, J., Zhang, Q.B., Tian, F., Feng, Y.Y., Guan, W.: Prediction of thermophysical properties of acetate-based ionic liquids using semiempirical methods. Ind. Eng. Chem. Res. 52, 9490–9496 (2013)

    Article  CAS  Google Scholar 

  7. Holbrey, J.D., Reichert, W.M., Tkatchenko, I., Bouajila, E., Walter, O., Tommasid, I., Rogers, R.D.: 1,3-Dimethylimidazolium-2-carboxylate: the unexpected synthesis of an ionic liquid precursor and carbene-CO2 adduct. Chem. Commun. 9, 28–29 (2003)

    Article  Google Scholar 

  8. Welton, T.: Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem. Rev. 99, 2071–2083 (1999)

    Article  CAS  Google Scholar 

  9. Earle, M.J., Sedden, K.R.: Ionic liquids. Green solvents for the future. Pure Appl. Chem. 72, 1391–1398 (2000)

    Article  CAS  Google Scholar 

  10. Villano, S.M., Gianola, A.J., Eyet, N., Ichino, T., Kato, S., Bierbaum, V.M., Lineberger, W.C.: Thermochemical studies of N-methylpyrazole and N-methylimidazole. J. Phys. Chem. A 111, 8579–8587 (2007)

    Article  CAS  Google Scholar 

  11. Mo, O., Yañez, M., Roux, M.V., Jiménez, P., Dávalos, J.Z., Ribeiro da Silva, M.A.V., Ribeiro da Silva, M.D.M.C., Matos, M.A.R., Amaral, L.M.P.F., Sánchez-Migallón, A., Cabildo, P., Claramunt, R., Elguero, J., Liebman, J.F.: Enthalpies of formation of n-substituted pyrazoles and imidazoles. J. Phys. Chem. A 103, 9336–9344 (1999)

    Article  CAS  Google Scholar 

  12. Zaitseva, K.V., Varfolomeev, M.A., Novikov, V.B., Solomonov, B.N.: Enthalpy of cooperative hydrogen bonding in complexes of tertiary amines with aliphatic alcohols: calorimetric study. J. Chem. Thermodyn. 43, 1083–1090 (2011)

    Article  CAS  Google Scholar 

  13. Lipkind, D., Plienrasri, C., Chickos, J.S.: A Study of the vaporization enthalpies of some 1-substituted imidazoles and pyrazoles by correlation-gas chromatography. J. Phys. Chem. B 114, 16959–16967 (2010)

    Article  CAS  Google Scholar 

  14. Verevkin, S.P., Zaitsau, D.H., Emel’yanenko, V.N., Paulechka, Y.U., Blokhin, A.V., Bazyleva, A.B., Kabo, G.J.: Thermodynamics of ionic liquids precursors: 1-methylimidazole. J. Phys. Chem. B 115, 4404–4411 (2011)

    Article  CAS  Google Scholar 

  15. Lipkind, D., Rath, N., Chickos, J.S., Pozdeev, V.A., Verevkin, S.P.: The vaporization enthalpies of 2- and 4-(N,N-dimethylamino)pyridine, 1,5-diazabicyclo[4.3.0]non-5-ene, 1,8-diazabicyclo[5.4.0]undec-7-ene, imidazo[1,2-a]pyridine and 1,2,4-triazolo[1,5-a]pyrimidine by correlation-gas chromatography. J. Phys. Chem. B 115, 8785–8796 (2011)

    Article  CAS  Google Scholar 

  16. Dohnal, V., Řehák, K.: Determination of infinite dilution partial molar excess enthalpies and volumes for some ionic liquid precursors in water and methanol using tandem flow mixing calorimetry and vibrating-tube densimetry. J. Chem. Eng. Data 56, 3047–3052 (2011)

    Article  CAS  Google Scholar 

  17. Gu, Z., Brennecke, J.F.: Volume expansivities and isothermal compressibilities of imidazolium and pyridinium-based ionic liquids. J. Chem. Eng. Data 47, 339–345 (2002)

    Article  CAS  Google Scholar 

  18. Huang, R., Du, R., Liu, G., Zhao, X., Ye, S., Wu, G.: A combined experimental and theoretical approach to the study of hydrogen bond interaction in the binary mixture of N-methylimidazole with water. J. Chem. Thermodyn. 55, 60–66 (2012)

    Article  CAS  Google Scholar 

  19. Guo, C., Fang, H., Huang, R.Y., Xu, H., Wu, G.H., Ye, S.Y.: Intermolecular interactions in binary system of 1-methylimidazole with methanol: a volumetric and theoretical investigation. Chem. Phys. Lett. 588, 97–101 (2013)

    Article  CAS  Google Scholar 

  20. Sun, X.F., Zhao, X.Y., Hou, H.Y., Wang, L., Zhu, X.J., Zhang, T., Yang, J.: Physicochemical properties of a binary mixture of N-methylimidazole and methanol. J. Mol. Liq. 216, 440–449 (2016)

    Article  CAS  Google Scholar 

  21. Zhu, X., Zhang, H., Li, H.: The structure of water in dilute aqueous solutions of ionic liquids: IR and NMR study. J. Mol. Liq. 197, 48–51 (2014)

    Article  CAS  Google Scholar 

  22. Hou, H., Jiao, B., Li, Q., Lin, X., Liu, M., Shi, H., Wang, L., Liu, S.: Physicochemical properties, NMR, ab initio calculations and the molecular interactions in a binary mixture of N-methylimidazole and water. J. Mol. Liq. 257, 100–111 (2018)

    Article  CAS  Google Scholar 

  23. González, B., Domínguez, A., Tojo, J.: Dynamic viscosities, densities, and speed of sound and derived properties of the binary systems acetic acid with water, methanol, ethanol, ethyl acetate and methyl acetate at T = (293.15, 298.15, and 303.15) K at atmospheric pressure. J. Chem. Eng. Data 49, 1590–1596 (2014)

    Article  Google Scholar 

  24. Orge, B., Iglesias, M., Rodríguez, A., Canosa, J.M., Tojo, J.: Mixing properties of (methanol, ethanol, or 1-propanol) with (n-pentane, n-hexane, n-heptane and n-octane) at 298.15 K. Fluid Phase Equilib. 133, 213–217 (1997)

    Article  CAS  Google Scholar 

  25. González, E.J., Alonso, L., Domínguez, Á.: Physical properties of binary mixtures of the ionic liquid 1-methyl-3-octylimidazolium chloride with methanol, ethanol, and 1-propanol at T = (298.15, 313.15, and 328.15) K and at p = 0.1 MPa. J. Chem. Eng. Data 51, 1446–1452 (2006)

    Article  Google Scholar 

  26. Mrad, S., Lafuente, C., Hichri, M., Khattech, I.: Density, speed of sound, refractive index, and viscosity of the binary mixtures of N,N-dimethylacetamide with methanol and ethanol. J. Chem. Eng. Data (2001). https://doi.org/10.1021/acs.jced.5b01000

    Article  Google Scholar 

  27. Rodríguez, A., Canosa, J., Tojo, J.: Physical properties of binary mixtures (dimethyl carbonate + alcohols) at several temperatures. J. Chem. Eng. Data 46, 1476–1486 (2001)

    Article  Google Scholar 

  28. Iglesias, M., Orge, B., Tojo, J.: Refractive indices, densities and excess properties on mixing of the systems acetone + methanol + water and acetone + methanol + 1-butanol at 298.15 K. Fluid Phase Equilib. 126, 203–233 (1996)

    Article  CAS  Google Scholar 

  29. Chen, S.P., Meng, X.X., Xie, G., Gao, S.L.: Thermochemistry of the ternary solid complex Er(C5H8NS2)3(C12H8N2). J. Chem. Eng. Data 50, 1204–1211 (2005)

    Article  CAS  Google Scholar 

  30. Wang, Z.J., Chen, S.P., Di, Y.Y., Yang, Q., Gao, S.L.: Enthalpy of solution of 5-R-Na2bdc·nH2O (H2bdc = isophthalic acid, R = H, NH2, OH, CH3, NO2) at 298.15 K. J. Chem. Eng. Data 55, 5786–5790 (2010)

    Article  CAS  Google Scholar 

  31. Zhang, R., Li, H., Lei, Y., Han, S.: All-atom molecular dynamic simulations and relative NMR spectra study of weak C– H···O contacts in amide–water systems. J. Phys. Chem. B 109, 7482–7487 (2005)

    Article  CAS  Google Scholar 

  32. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Peralta Jr., J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Staroverov, K.N., Kudin, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J., Fox, D.J.: Gaussian 09 (Revision A.02). Gaussian, Inc., Wallingford, CT (2009)

  33. Boys, S.F., Bernardi, F.: The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors. Mol. Phys. 19, 553–566 (1970)

    Article  CAS  Google Scholar 

  34. Reed, A.E., Curtiss, L.A., Weinhold, F.: Intermolecular interactions from a natural bond orbital, donor–acceptor viewpoint. Chem. Rev. 88, 899–926 (1988)

    Article  CAS  Google Scholar 

  35. Biegler-König, F.: AIM2000. University of Applied Sciences, Bielefeld (2000)

    Google Scholar 

  36. Kapadi, U.R., Hundiwale, D.G., Patil, N.B., Lande, M.K.: Effect of temperature on excess molar volumes and viscosities of binary mixtures of ethylenediamine and water. Fluid Phase Equilib. 205, 267–274 (2003)

    Article  CAS  Google Scholar 

  37. Guo, Z.H., Zhang, J.B., Zhang, T., Li, C.P., Zhang, Y.F., Bai, J.: Liquid viscosities, excess properties, and viscous flow thermodynamics of triethylene glycol + water mixtures at T = (298.15, 303.15, 308.15, 313.15, and 318.15) K. J. Mol. Liq. 165, 27–31 (2012)

    Article  CAS  Google Scholar 

  38. Xu, Q., Sun, S., Lan, G., Xiao, J., Zhang, J., Wei, X.: Excess properties and spectral investigation for the binary system diethylene glycol dimethyl ether + water at T = (293.15, 298.15,303.15, 308.15, and 313.15) K. J. Chem. Eng. Data 60, 2–10 (2015)

    Article  CAS  Google Scholar 

  39. Zarrougui, R., Dhahbi, M., Lemordant, D.: Transport and thermodynamic properties of ethylammonium nitrate–water binary mixtures: effect of temperature and composition. J. Solution Chem. 44, 686–702 (2015)

    Article  CAS  Google Scholar 

  40. Wang, J., Tian, Y., Zhao, Y., Zhuo, K.: A volumetric and viscosity study for the mixtures of 1-n-butyl-3-methylimidazolium tetrafluoroborate ionic liquid with acetonitrile, dichloromethane, 2-butanone and N,N-dimethylformamide. Green Chem. 5, 618–622 (2003)

    Article  CAS  Google Scholar 

  41. Pires, J., Timperman, L., Jacquemin, J., Balducci, A., Anouti, M.: Density, conductivity, viscosity, and excess properties of (pyrrolidinium nitrate-based protic ionic liquid + propylene carbonate) binary mixture. J. Chem. Thermodyn. 59, 10–19 (2013)

    Article  CAS  Google Scholar 

  42. Reis, J.C.R., Lampreia, I.M.S., Santos, Â.F.S., Moita, M.L.C.J., Douhéret, G.: Refractive index of liquid mixtures: theory and experiment. Chem. Phys. Chem. 11, 3722–3733 (2010)

    Article  CAS  Google Scholar 

  43. Brocos, P., Piñeiro, Á., Bravo, R., Amigo, A.: Refractive indices, molar volumes and molar refractions of binary liquid mixtures: concepts and correlations. Phys. Chem. Chem. Phys. 5, 550–557 (2003)

    Article  CAS  Google Scholar 

  44. Iglesias-Otero, M.A., Troncoso, J., Carballo, E., Romaní, L.: Density and refractive index in mixtures of ionic liquids and organic solvents: correlations and predictions. J. Chem. Thermodyn. 40, 949–956 (2008)

    Article  CAS  Google Scholar 

  45. Podgoršek, A., Jacquemin, J., Pádua, A.A.H., Costa Gomes, M.F.: Mixing enthalpy for binary mixtures containing ionic liquids. Chem. Rev. 116, 6075–6106 (2016)

    Article  Google Scholar 

  46. Yan, X.J., Li, S.N., Zhai, Q.G., Jiang, Y.C., Hu, M.C.: Physicochemical properties for the binary systems of ionic liquids [Cnmim]Cl + N,N-dimethylformamide. J. Chem. Eng. Data 59, 1411–1422 (2014)

    Article  CAS  Google Scholar 

  47. Dubey, G.P., Kumar, K.: Density, speed of sound, viscosity, excess properties, and Prigogine–Flory–Patterson (PFP) theory of binary mixtures of amine and alcohols. J. Chem. Eng. Data 61, 1967–1980 (2016)

    Article  CAS  Google Scholar 

  48. Oswal, S.L., Desai, H.S.: Studies of viscosity and excess molar volume of binary mixtures: 1. Propylamine + 1-alkanol mixtures at 303.15 and 313.15 K. Fluid Phase Equilib. 149, 359–376 (1998)

    Article  CAS  Google Scholar 

  49. González, J.A., Alonso, I., De La Fuente, I.G., Cobos, J.C.: Thermodynamics of ketone + amine mixtures. Part X. Excess molar enthalpies at 298.15 K for N,N, N-triethylamine + 2-alkanone systems. Characterization of tertiary amine + 2-alkanone, and of amino–ketone + n-alkane mixtures in terms of DISQUAC. Fluid Phase Equilibr. 356, 117–125 (2013)

    Article  Google Scholar 

  50. Zhuo, K., Chen, Y., Chen, J., Bai, G., Wang, J.: Interactions of 1-butyl-3-methylimidazolium carboxylate ionic liquids with glucose in water: a study of volumetric properties, viscosity, conductivity and NMR. Phys. Chem. Chem. Phys. 13, 14542–14549 (2011)

    Article  CAS  Google Scholar 

  51. Reichardt, C.: Solvent and Solvent Effects in Organic Chemistry, 3rd edn. Wiley-VCH Verlag GmbH & Co, KGaA, Weinheim (2003)

    Google Scholar 

  52. Catalan, J., Couto, A., Gornez, J., Saiz, J.L., Laynez, J.: Towards a solvent acidity scale: the calorimetry of the N-methyl imidazole probe. J. Chem. Soc. Perkin Trans. 2, 1181–1185 (1992)

    Article  Google Scholar 

  53. Catalan, J., De Paz, J.L.G., Yaiiez, M., Claramunt, R.M., Lopez, C., Elguero, J., Anvia, F., Quian, J.H., Taagepera, M., Taft, R.W.: A theoretical and experimental study of the intrinsic basicities of methyldiazoles. J. Am. Chem. Soc. 112, 1303–1312 (1990)

    Article  CAS  Google Scholar 

  54. Vreekamp, R., Castellano, D., Palomar, J., Ortega, J., Espiau, F., Fernández, L., Penco, E.: Thermodynamic behavior of the binaries 1-butylpyridinium tetrafluoroborate with water and alkanols: their interpretation using 1H NMR spectroscopy and quantum-chemistry calculations. J. Phys. Chem. B 115, 8763–8774 (2011)

    Article  CAS  Google Scholar 

  55. Chen, Y., Cao, Y., Sun, X., Mu, T.: Hydrogen bonding interaction between acetate-based ionic liquid 1-ethyl-3-methylimidazolium acetate and common solvents. J. Mol. Liq. 190, 151–158 (2014)

    Article  CAS  Google Scholar 

  56. Chen, Y., Cao, Y., Zhang, Y., Mu, T.: Hydrogen bonding between acetate- based ionic liquids and water: three types of IR absorption peaks and NMR chemical shifts change upon dilution. J. Mol. Struct. 1058, 244–251 (2014)

    Article  CAS  Google Scholar 

  57. Gupta, S., Rafiq, S., Kundu, M., Sen, P.: Origin of strong synergism in weakly perturbed binary solvent system: a case study of primary alcohols and chlorinated methanes. J. Phys. Chem. B 116, 1345–1355 (2012)

    Article  CAS  Google Scholar 

  58. Mizuno, K., Ochi, T., Shindo, Y.: Hydrophobic hydration of acetone probed by nuclear magnetic resonance and infrared: evidence for the interaction C-HOH2. J. Chem. Phys. 109, 9502–9507 (1998)

    Article  CAS  Google Scholar 

  59. Mizunoa, K., Kimurab, Y., Morichikab, H., Nishimurab, Y., Shimadab, S., Maedab, S., Imafujib, S., Ochib, T.: Hydrophobic hydration of tert-butyl alcohol probed by NMR and IR. J. Mol. Liq. 85, 139–152 (2000)

    Article  Google Scholar 

  60. Mizunoa, K.: Hydration of the CH groups in dimethyl sulfoxide probed by NMR and IR. J. Phys. Chem. B 104, 11001–11005 (2000)

    Article  Google Scholar 

  61. Li, Q., Wu, G., Yu, Z.: The role of methyl group in the formation of hydrogen bond in DMSO–methanol mixtures. J. Am. Chem. Soc. 128, 1438–1439 (2006)

    Article  CAS  Google Scholar 

  62. Gupta, S., Parida, K.N., Mukherjee, P., Sen, P.: Mixed solvent chemistry through synergistic solvation: structure, property and function of t-butanol–dichloromethane binary solvent mixtures. J. Solution Chem. 46, 461–475 (2017)

    Article  CAS  Google Scholar 

  63. Gupta, S., Chakraborty, A., Sen, P.: Elucidation of intriguing methanol–dichloromethane binary solvent mixture: synergistic effect, analytical modeling, NMR and photo-induced electron transfer studies. J. Mol. Liq. 223, 274–282 (2016)

    Article  CAS  Google Scholar 

  64. Arunan, E., Desiraju, G.R., Klein, R.A., Sadlej, J., Scheiner, S., Alkorta, I., Clary, D.C., Crabtree, R.H., Dannenberg, J.J., Hobza, P., Kjaergaard, H.G., Legon, A.C., Mennucci, B., Nesbitt, D.J.: Definition of the hydrogen bond (IUPAC recommendations 2011). Pure Appl. Chem. (2012). https://doi.org/10.1351/PAC-REC-10-01-02

    Article  Google Scholar 

  65. Li, Q.Z., Li, R., Liu, X.F., Li, W.Z., Cheng, J.B.: Concerted Interaction between pnicogen and halogen bonds in XCl–FH2P–NH3 (X = F, OH, CN, NC, and FCC). Chem. Phys. Chem. 13, 1205–1212 (2012)

    Article  CAS  Google Scholar 

  66. Koch, U., Popelier, P.L.A.: Characterization of C-H-O hydrogen bonds on the basis of the charge density. J. Phys. Chem. 99, 9747–9754 (1995)

    Article  CAS  Google Scholar 

  67. Arnold, W.D., Oldfield, E.: The chemical nature of hydrogen bonding in proteins via NMR: J-couplings, chemical shifts, and AIM theory. J. Am. Chem. Soc. 122, 12835–12841 (2000)

    Article  CAS  Google Scholar 

Download references

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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