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Gas- and liquid-phase ozonolysis of ethylene, butadiene, and perfluoro-olefins: solvation and the cage effect

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Abstract

Quantum-chemical calculations were performed for the primary step of ozonolysis reaction of different olefins: ethylene, 1,3-butadiene, 1,1,2,2-tetrafluoroethylene, 1,1,2,3,3,3-hexafluoropropylene using B2PLYP functional (basis sets are: aug-cc-pVDZ and aug-cc-pVTZ) and M06-2x functional (6–311++G** and 6–311++G(2df,2pd)) in both gas and liquid phases. Solvent influence (water and carbon tetrachloride/tetrachloroethylene) is taken into account using the polarized continuum model (PCM), the solvation model based on density (SMD) and the Onsager model. Rate constants for the different reaction paths of addition were found. The kinetic parameters (activation enthalpy, activation entropy) are found in terms of transition state theory based on consideration of stationary points on potential energy surface. It is shown that the more solvent polarity increases the more solvation and the rate constant increase. Interestingly, this effect takes place for the both Criegee and DeMore addition channels; the last one increases more greatly. Comparisons with experimental data made it possible to estimate the effect of solvation and the cage effect separately for this reaction.

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Notes

  1. Zero-point vibration energy correction is much lower than electronic energy and moreover it has the same value and sign because it is computed in terms of the same DFT method, namely, B2PLYP.

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Acknowledgements

The work was carried out using the equipment of the Center of Shared Usage “New Materials and Technologies of Emanuel Institute of Biochemical Physics,” Joint Research Center of Plekhanov Russian University of Economics, and Mass Spectrometry Data Center of National Institute of Standards and Technology, Gaithersburg, United States of America. This work was performed in accordance with the state task, state registration no. AAAA-A19-119101690058-9.

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Authors and Affiliations

  1. Institute of Problems of Chemical Physics of RAS, Chernogolovka, Russia

    Boris E. Krisyuk

  2. PLEKHANOV Russian University of Economics, Moscow, Russia

    Boris E. Krisyuk & Eldar A. Mamin

  3. N. M. Emanuel Institute of Biochemical Physics of RAS, Moscow, Russia

    Eldar A. Mamin

  4. National Institute of Standards and Technology, Gaithersburg, MD, USA

    Alexey V. Mayorov

  5. A.A. Kharkevich Institute for Information Transmission Problems, Moscow, Russia

    Alexey V. Mayorov

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  1. Boris E. Krisyuk
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Krisyuk, B.E., Mayorov, A.V. & Mamin, E.A. Gas- and liquid-phase ozonolysis of ethylene, butadiene, and perfluoro-olefins: solvation and the cage effect. Monatsh Chem 153, 609–621 (2022). https://doi.org/10.1007/s00706-022-02946-4

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