Abstract
Enthalpy of solvation is an important thermodynamic property for studying molecular interactions. However, measuring enthalpies of solvation is non-trivial and time-consuming. Therefore, models that can predict enthalpy of solvation values are of significant worth to the general community. Here we present such models, based upon the Acree enthalpy of solvation open data dataset, which can be used to predict enthalpy of solvation values directly from structure. We created machine learning models for enthalpies of solvation in ethanol using open Chemistry Development Kit descriptors that have overall test-set R2 values of 0.89–0.90 and test-set root mean squared error values of 6.60–7.10 kJ·mol−1. The accuracy of the models was improved by limiting them to a single dominant cluster. Since our models were developed under Open Notebook Science conditions, they are fully reproducible and our techniques transparent and easily adaptable to other solvents.
Similar content being viewed by others
References
Varfolomeev, M.A., Rakipov, I.T., Acree Jr., W.E., Brumfield, M., Abraham, M.H.: Examination of hydrogen-bonding interactions between dissolved solutes and alkylbenzene solvents based on Abraham model correlations derived from measured enthalpies of solvation. Thermochim. Acta 594, 68–79 (2014)
Wilson, A., Tian, A., Dabadge, N., Acree Jr., W.E., Varfolomeev, M.A., Rakipov, I.T., Arkhipova, S.M., Abraham, M.H.: Enthalpy of solvation correlations for organic solutes and gases dissolved in dichloromethane and 1,4-dioxane. Struct. Chem. 24(6), 1841–1853 (2013)
Solomonov, B.N., Varfolomeev, M.A., Novikov, V.B., Klimovitskii, A.E., Faizullin, D.A.: The influence of H-bonding on the enthalpies of solvation of proton acceptors in methanol. Russ. J. Phys. Chem. 79(7), 1029–1032 (2005)
Mintz, C., Clark, M., Acree Jr., W.E., Abraham, M.H.: Enthalpy of solvation correlations for gaseous solutes dissolved in water and in 1-octanol based on the Abraham model. J. Chem. Inf. Model. 47(1), 115–121 (2007)
Mintz, C., Clark, M., Burton, K., Acree Jr., W.E., Abraham, M.H.: Enthalpy of solvation correlations for gaseous solutes dissolved in toluene and carbon tetrachloride based on the Abraham model. J. Solution Chem. 36(8), 947–966 (2007)
Mintz, C., Burton, K., Acree Jr., W.E., Abraham, M.H.: Enthalpy of solvation correlations for gaseous solutes dissolved in chloroform and 1,2-dichloroethane based on the Abraham model. Fluid Phase Equilib. 258(2), 191–198 (2007)
Mintz, C., Clark, M., Burton, K., Acree Jr., W.E., Abraham, M.H.: Enthalpy of solvation correlations for gaseous solutes dissolved in benzene and in alkane solvents based on the Abraham model. QSAR Comb. Sci. 26(8), 881–888 (2007)
Mintz, C., Burton, K., Ladlie, T., Clark, M., Acree Jr., W.E., Abraham, M.H.: Enthalpy of solvation correlations for gaseous solutes dissolved in dibutyl ether and ethyl acetate. Thermochim. Acta 470(1–2), 67–76 (2008)
Mintz, C., Ladlie, T., Burton, K., Clark, M., Acree Jr., W.E., Abraham, M.H.: Enthalpy of solvation correlations for gaseous solutes dissolved in alcohol solvents based on the Abraham model. QSAR Comb. Sci. 27(5), 627–635 (2008)
Stolov, M.A., Zaitseva, K.V., Varfolomeev, M.A., Acree Jr., W.E., Abraham, M.H.: Enthalpies of solution and enthalpies of solvation of organic solutes in ethylene glycol at 298.15 K: prediction and analysis of intermolecular interaction contributions. Thermochim. Acta 648, 91–99 (2017)
Varfolomeev, M.A., Rakipov, I.T., Khachatrian, A.A., Acree Jr., W.E., Brumfield, M., Abraham, M.H.: Effect of halogen substitution on the enthalpies of solvation and hydrogen bonding of organic solutes in chlorobenzene and 1,2-dichlorobenzene derived using multi-parameter correlations. Thermochim. Acta 617, 8–20 (2015)
Hart, E., Grover, D., Zettl, H., Acree Jr., W.E., Abraham, M.H.: Abraham model enthalpy of solvation correlations for solutes dissolved in dimethyl carbonate and diethyl carbonate. Phys. Chem. Liq. 53(6), 732–747 (2015)
Hart, E., Zettl, H., Grover, D., Acree Jr., W.E., Abraham, M.H.: Abraham model enthalpy of solvation correlations for solutes dissolved in 1-alkanol solvents (C4–C6). Phys. Chem. Liq. 53(5), 638–659 (2015)
Stephens, T.W., De La Rosa, N.E., Saifullah, M., Ye, S., Chou, V., Quay, A.N., Acree Jr., W.E., Abraham, M.H.: Enthalpy of solvation correlations for organic solutes and gases dissolved in 2-propanol, 2-butanol, 2-methyl-1-propanol and ethanol. Thermochim. Acta 523(1–2), 214–220 (2011)
Naef, R., Acree, W.E.: Calculation of five thermodynamic molecular descriptors by means of a general computer algorithm based on the group-additivity method: standard enthalpies of vaporization, sublimation and solvation, and entropy of fusion of ordinary organic molecules and total phase-change entropy of liquid crystals. Molecules 22(7), 1059 (2017)
Dashtbozorgi, Z., Golmohammadi, H., Acree Jr., W.E.: Prediction of gas to water solvation enthalpy of organic compounds using support vector machines. Thermochim. Acta 539, 7–15 (2012)
Golmohammadi, H., Dashtbozorgi, Z., Samani, M.G., Acree Jr., W.E.: QSPR prediction of gas-to-methanol solvation enthalpy of organic compounds using replacement method and support vector machines. Phys. Chem. Liq. 53(1), 46–66 (2015)
Golmohammadi, H., Dashtbozorgi, Z., Acree Jr., W.E.: QSPR models for prediction of gas-to-heptane and gas-to-hexadecane solvation enthalpies of organic compounds from theoretical molecular descriptors. Struct. Chem. 24(6), 1799–1810 (2013)
Acree, W.E. Jr., Lang, A.S.I.D.: Acree enthalpy of solvation dataset. figshare. (2015) https://doi.org/10.6084/m9.figshare.1572326.v1
Bradley, J.-C., Lang, A.S.I.D., Koch, S., Neylon, C.: Collaboration using Open Notebook Science in academia. In: Ekin, S., Hupcey, M.A.Z., Williams, A.J., Bingham, A. (eds.) Collaborative Computational Technologies for Biomedical Research, pp. 423–452. Wiley, New York (2011)
Jaquis, B.J., Lang, A.S.I.D., Li, A., Monnier, N.D.: Enthalpy of solvation in ethanol. wikidot.com (2018) http://oruons.wikidot.com/enthalpy-of-solvation. Accessed 31 May 2018
Guha, R.: CDK Descriptor GUI (v 1.4.8). GitHub (2017). https://github.com/rajarshi/cdkdescui. Accessed 31 May 2018
Steinbeck, C., Han, Y., Kuhn, S., Horlacher, O., Luttmann, E., Willighagen, E.: The chemistry development kit (CDK): an open-source java library for chemo- and bioinformatics. J. Chem. Inf. Comput. Sci. 43(2), 493–500 (2003)
Willighagen, E., Mayfield, J.W., Alvarsson, J., Berg, A., Carlsson, L., Jeliazkova, N., Kuhn, S., Pluskal, T., Rojas-Chertó, M., Spjuth, O., Torrance, G., Evelo, C.T., Guha, R., Steinbeck, C.: The Chemistry Development Kit (CDK): v2.0 atom typing, depiction, molecular formulas, and substructure searching. J. Cheminform. 9, 33 (2017)
R Core Team: R: A Language and Environment for Statistical Computing. R Foundation for Statistical Computing, Vienna, Austria (2013) http://www.R-project.org/. Accessed 31 May 2018
Kuhn, M.: Building predictive models in R using the Caret Package. J. Stat.Soft. 28 (2008) https://doi.org/10.18637/jss.v028.i05
Liaw, A., Wiener, M.: Classification and Regression by randomForest. R news 2/3 (2002)
Candel, A., LeDell, E.: Deep Learning with H2O. Bartz, A., editor. H2O.ai Inc. (2018) http://h2o.ai/resources/. Accessed 31 May 2018
Acknowledgements
The authors acknowledge the influence of Jean-Claude Bradley and his advocacy for Open Science on this work.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Jaquis, B.J., Li, A., Monnier, N.D. et al. Using Machine Learning to Predict Enthalpy of Solvation. J Solution Chem 48, 564–573 (2019). https://doi.org/10.1007/s10953-019-00867-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10953-019-00867-1