Predictive Models for the Free Energy of Hydrogen Bonded Complexes with Single and Cooperative Hydrogen Bondsстатья

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[1] Predictive models for the free energy of hydrogen bonded complexes with single and cooperative hydrogen bonds / M. Glavatskikh, T. Madzhidov, V. Solov’ev et al. // Molecular informatics. — 2016. — Vol. 35, no. 11-12. — P. 629–638. In this work, we report QSPR modeling of the free energy DG of 1:1 hydrogen bond complexes of differ- ent H-bond acceptors and donors. The modeling was per- formed on a large and structurally diverse set of 3373 com- plexes featuring a single hydrogen bond, for which DG was measured at 298 K in CCl4. The models were prepared using Support Vector Machine and Multiple Linear Regres- sion, with ISIDA fragment descriptors. The marked atoms strategy was applied at fragmentation stage, in order to capture the location of H-bond donor and acceptor centers. Different strategies of model validation have been suggest- ed, including the targeted omission of individual H-bond acceptors and donors from the training set, in order to check whether the predictive ability of the model is not limited to the interpolation of H-bond strength between two already encountered partners. Successfully cross-vali- dating individual models were combined into a consensus model, and challenged to predict external test sets of 629 and 12 complexes, in which donor and acceptor formed single and cooperative H-bonds, respectively. In all cases, SVM models outperform MLR. The SVM consensus model performs well both in 3-fold cross-validation (RMSE= 1.50 kJ/mol), and on the external test sets containing com- plexes with single (RMSE=3.20 kJ/mol) and cooperative H- bonds (RMSE=1.63 kJ/mol). [ DOI ]

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