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Structure-reactivity relationships in terms of the condensed graphs of reactions

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Abstract

An approach for the prediction of rate constants of chemical reactions, based on the representation of a chemical reaction as a condensed graph, has been tested on more than 1000 bimolecular nucleophilic substitution reactions with neutral nucleophiles in 38 solvents. Molecular fragment descriptors, temperature, and solvent parameters characterizing solvation power have been used in the reaction modeling. The obtained models ensure a good correlation between the predicted and experimental values; the corresponding deviations are comparable with interlaboratory measurement errors.

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Authors and Affiliations

  1. Kazan (Volga Region) Federal University, ul. Kremlevskaya 18, Kazan, 420008, Tatarstan, Russia

    T. I. Madzhidov, R. I. Nugmanov, A. V. Bodrov, A. I. Lin & I. S. Antipin

  2. Bogatskii Physicochemical Institute, National Academy of Sciences of Ukraine, Lyustdorfskaya doroga 86, Odessa, 65080, Ukraine

    P. G. Polishchuk

  3. Faculty of Chemistry, Moscow State University, Vorob’evy gory 1, Moscow, 119991, Russia

    I. I. Baskin

  4. Chemoinformatics Laboratory, University of Strasbourg, rue B. Pascal 4, CS 90032, Strasbourg, 67000, France

    I. I. Baskin & A. A. Varnek

Authors
  1. T. I. Madzhidov
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  2. P. G. Polishchuk
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  3. R. I. Nugmanov
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  4. A. V. Bodrov
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  5. A. I. Lin
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  6. I. I. Baskin
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  7. A. A. Varnek
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  8. I. S. Antipin
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Correspondence to T. I. Madzhidov.

Additional information

Original Russian Text © T.I. Madzhidov, P.G. Polishchuk, R.I. Nugmanov, A.V. Bodrov, A.I. Lin, I.I. Baskin, A.A. Varnek, I.S. Antipin, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 4, pp. 473–478.

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Madzhidov, T.I., Polishchuk, P.G., Nugmanov, R.I. et al. Structure-reactivity relationships in terms of the condensed graphs of reactions. Russ J Org Chem 50, 459–463 (2014). https://doi.org/10.1134/S1070428014040010

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  • DOI: https://doi.org/10.1134/S1070428014040010

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