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Structure–reactivity relationship in Diels–Alder reactions obtained using the condensed reaction graph approach

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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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Authors and Affiliations

  1. Kazan Federal University, Kazan, Russia

    T. I. Madzhidov, T. R. Gimadiev, D. A. Malakhova, R. I. Nugmanov, I. S. Antipin & A. A. Varnek

  2. University of Strasbourg, Strasbourg, France

    T. R. Gimadiev & A. A. Varnek

  3. Moscow State University, Moscow, Russia

    I. I. Baskin

Authors
  1. T. I. Madzhidov
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  2. T. R. Gimadiev
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  3. D. A. Malakhova
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  4. R. I. Nugmanov
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  5. I. I. Baskin
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  6. I. S. Antipin
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  7. A. A. Varnek
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Corresponding author

Correspondence to T. I. Madzhidov.

Additional information

Original Russian Text © 2017 T. I. Madzhidov, T. R. Gimadiev, D. A. Malakhova, R. I. Nugmanov, I. I. Baskin,I. S. Antipin, A. A. Varnek.

Translated from Zhurnal Strukturnoi Khimii, Vol. 58, No. 4, pp. 685–691, July–August, 2017.

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Madzhidov, T.I., Gimadiev, T.R., Malakhova, D.A. et al. Structure–reactivity relationship in Diels–Alder reactions obtained using the condensed reaction graph approach. J Struct Chem 58, 650–656 (2017). https://doi.org/10.1134/S0022476617040023

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  • DOI: https://doi.org/10.1134/S0022476617040023

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