STRUCTURE-REACTIVITY RELATIONSHIP IN DIELS-ALDER REACTIONS OBTAINED USING THE CONDENSED REACTION GRAPH APPROACH
T. I. Madzhidov1, T. R. Gimadiev1,2, D. A. Malakhova1, R. I. Nugmanov1, I. I. Baskin3, I. S. Antipin1, A. A. Varnek1,2
1Kazan Federal University, Kazan, Russia
2University of Strasbourg, Strasbourg, France
3Moscow State University, Moscow, Russia
Keywords: [4+2]π-циклоприсоединение, реакция Дильса-Альдера, константа скорости реакции, конденсированный граф реакции, химические реакции, хемоинформатика, [4+2]π-cycloaddition, Diels-Alder reaction, rate constant, condensed graph of the reaction, chemical reactions, chemoinformatics
Abstract
By the structural representation of a chemical reaction in the form of a condensed graph a model allowing the prediction of rate constants (logk) of Diels-Alder reactions performed in different solvents and at different temperatures is constructed for the first time. The model demonstrates good agreement between the predicted and experimental logk values: the mean squared error is less than 0.75 log units. Erroneous predictions correspond to reactions in which reagents contain rarely occurring structural fragments. The model is available for users at https://cimm.kpfu.ru/predictor/.
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