Prediction of Melting Temperature of bis(trifluoromethylsulfonyl) Imide Anion Based Ionic Liquids Using QSPR Approach

Document Type : Research Article

Authors

Department of Chemistry, Sharif University of Technology, Tehran, I.R. IRAN

Abstract

In this study, the melting temperature of ionic liquids based on bis(trifluoromethylsulfonyl)imide anion using experimental data were modeled using the QSPR approach. The structures of ionic liquids were drawn by Avogadro software and their 3D structure were optimized by Merck molecular force field. Descriptors were calculated using Dragon and Padel software. After reducing the number of descriptors, the ionic liquids were divided into training and test set employing Kenard- Stone algorithm. For choosing the best set of descriptors, a genetic algorithm with Friedman's lack of fitness was used. Then, the numbers of optimized variables were determined by the multiple linear regression MLR method and the linear equation between variables was obtained. Linear and nonlinear models were built by means of Multiple Linear Regressions (MLR), MultiLayer Perceptron (MLP) neural networks, and using genetic algorithm. R2, AARD values were 0.787, 0.043 for linear model and 0.785, 0.0428, for nonlinear model. Both models showed the same accuracy. The applicability domain of the proposed models was also determined. Also using the obtained descriptors, the effect of molecular structure on the physical properties such as melting temperature was addressed.

Keywords

Main Subjects

References

[1] Earle M.J., Seddon K.R., Ionic Liquids. Green Solvents for the Future, Pure Appl. Chem., 72: 1391-1398 (2000).
[2] Keskin S., Kayrak-Talay D., Akman U., Hortaçsu Ö., A Review of Ionic Liquids Towards Supercritical Fluid Applications, J. Supercrit. Fluids., 43: 150–180 (2007).
[3] Gardas R.L., Freire M.G., Carvalho P.J., Marrucho I.M., Fonseca I.M.A., Ferreira A.G.M., Coutinho J.A.P., A Review of Ionic Liquids Towards Supercritical Fluid Applications, J. Chem. Eng. Data., 52: 80–88 (2007).
[4] Seki S., Kobayashi T., Kobayashi Y., Takei K.., Miyashiro H., Hayamizu K.., Tsuzuki S., Mitsugi, T., Umebayashi Y., Effects of Cation and Anion on Physical Properties of Room-Temperature Ionic Liquids, J. Mol. Liq., 152: 9–13(2010).
[5] Zhang S., Sun N., He X., Lu X., Zhang X., Physical Properties of Ionic Liquids: Database and Evaluation, J. Phys. Chem. Ref. Data, 35: 1475–1517 (2006).
[6] Wang X., Chi Y., Mu T., A Review on the Transport Properties of Ionic Liquids, J. Mol. Liq., 193: 262–266 (2014).
[7] Plechkova N.V., Seddon K.R., Applications of Ionic Liquids in the Chemical Industry, Chem. Soc. Rev., 37: 123–150 (2008).
[8] Katritzky A. R., Lomaka A., PetruĜ³khin R., Jain R., Karelson M., Visser A. E., Rogers R. D., QSPR Correlation of the Melting Point for Pyridinium Bromides, Potential Ionic Liquids, J. Chem. Inf. Comput. Sci., 42: 71-74 (2002). 
[9] Trohalaki S., Pachter R., Drake G. W., Hawkins T., Quantitative Structure-Property Relationships for Melting Points and Densities of Ionic Liquids, Energy Fuels, 19: 279-284 (2005).
[10] Ren Y., Qin J., Liu H., Yao X., Liu M., QSPR Study on the Melting Points of a Diverse Set of Potential Ionic Liquids by Projection Pursuit Regression, QSAR Comb. Sci., 28: 1237–1244 (2009).
[11] https://ilthermo.boulder.nist.gov (accessed 2017)
[12] Hanwell M. D., Curtis D. E., Lonie D. C., Vandermeersch T., Zurek E., Geoffrey R., Hutchison Avogadro: an Advanced Semantic Chemical Editor, Visualization, and Analysis Platform., J. Chem., 4: 17-23 (2012).
[13] Yap C. W., PaDEL-Descriptor: An Open Source Software to Calculate Molecular Descriptors and Fingerprints, J. Comput. Chem., 32: 1466-1474(2011).
[14] Mauri A., Consonni V., Pavan M., Todeschini, R., Dragon Software: an Easy Approach to Molecular Descriptor Calculations, Match, 56: 237-248 (2006.).
[15] Kennard R.W., Stone L.A., Computer-Aided Design of Experiments, Technomet., 11: 137–148 (1969).
[16] http://accelrys.com/products/collaborative-science/biovia-materials-studio/
[17] Todeschini R., Consonni V., "Handbook of Molecular Descriptors", WILEY-VCH Verlag GmbH. (2000).
[18] Haupt R.L., Haupt E., "Practical Genetic Algorithms", 2 nd ed., John Wiley & Sons, Inc. (2004).

Files

Share

How to cite

Statistics