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Diels–Alder Reaction as an Indicator of Internal and External Factors Influencing the Rate and Equilibrium: Kinetics, Thermochemistry, Catalysis, and High Pressure. A Review

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Abstract

The Diels–Alder reaction (DAR), in addition to its enormous synthetic potential, is the most reliable testing ground for quantitative research of the influence of various internal and external factors on the rate and equilibrium. The influence of the energy of intermolecular orbital interaction and then the influence of the enthalpy of reaction have been considered. It has been demonstrated that the DAR rate can be described when both factors are considered jointly. Kinetic and thermochemical data for DAR in the presence of Lewis acids are discussed. New data on the DAR rate during grinding reagents in the solid phase generate many problems for further study. Finally, the analysis of extensive data on the high pressure effect on the DAR rate and equilibrium have allowed the conclusion that differences in activation volumes and reaction volumes are not related to the mechanism of the DAR.

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ACKNOWLEDGMENTS

The authors are grateful to Academician B.A. Arbuzov for the initial call for a quantitative study of the DAR in the framework of physical organic chemistry.

Academician A.I. Konovalov died a few days before the manuscript was accepted for publication. Under the leadership of Academician A.I. Konovalov and with his direct participation, the origin of the “anomalous” kinetic selectivity of reagents in the DAR has been elucidated for the first time, the possibility of an intermediate “neutral” type of DAR has been experimentally confirmed, and an abundant amount of kinetic and thermochemical data that formed the basis of this review has been obtained.

Funding

This work was supported by the Foundation of the Government of the Russian Federation in the framework of a state assignment in the field of scientific activity (project no. 0671-2020-0061).

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  1. Butlerov Chemical Institute, Kazan Federal University, 420008, Kazan, Russia

    A. I. Konovalov, D. A. Kornilov & V. D. Kiselev

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  1. A. I. Konovalov
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  2. D. A. Kornilov
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  3. V. D. Kiselev
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Correspondence to V. D. Kiselev.

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Translated by G. Kirakosyan

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Konovalov, A.I., Kornilov, D.A. & Kiselev, V.D. Diels–Alder Reaction as an Indicator of Internal and External Factors Influencing the Rate and Equilibrium: Kinetics, Thermochemistry, Catalysis, and High Pressure. A Review. Dokl Chem 498, 67–92 (2021). https://doi.org/10.1134/S0012500821050013

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