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Cross effects of structure and temperature in the reactions of trans-2,3-diaryloxiranes with arenesulfonic acids

Abstract

Cross effects of the reagent structure and the temperature on the rate and activation parameters of the reactions of symmetrically X-substituted trans-2,3-diaryloxiranes with Y-substituted arene-sulfonic acids have been investigated in the temperature range 265–298 K. The isokinetic temperature of 265 K was reached, at which the rate and the free energy of the ring-opening reaction of trans-2,3-bis(3-bromo-5-nitrophenyl)-oxirane practically do not depend on substituent Y. The transition through the isoparametric points on substituent Y was realized with the inversion of the temperature effect on the free energy of activation for the reactions of oxiranes with X = 4-NO2 and 3-Br-5-NO2.

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Correspondence to I. V. Shpan’ko.

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Original Russian Text © I.V. Shpan’ko, I.V. Sadovaya, 2017, published in Zhurnal Obshchei Khimii, 2017, Vol. 87, No. 11, pp. 1810–1816.

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Shpan’ko, I.V., Sadovaya, I.V. Cross effects of structure and temperature in the reactions of trans-2,3-diaryloxiranes with arenesulfonic acids. Russ J Gen Chem 87, 2552–2557 (2017). https://doi.org/10.1134/S107036321711007X

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  • DOI: https://doi.org/10.1134/S107036321711007X

Keywords

  • trans-2,3-diaryloxiranes
  • arenesulfonic acids
  • phenomenon of isoparametricity
  • compensation effect