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Reactions of alkoxy and peroxy radicals formed upon the decomposition of hydroxyperoxide groups in the artemisinin derivatives

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Abstract

The enthalpies of intramolecular reactions of alkoxy and peroxy radicals formed from polyatomic artemisinin hydroperoxides and of their bimolecular reactions with C—H, S—H, and O—H bonds of biological substrates were calculated. The activation energies and rate constants of these reactions were calculated using the intersecting parabolas method. The decomposition of artemisinin hydroperoxides can initiate the cascade of intramolecular oxidation reactions involving radicals R·, RO·, HO·, HO2·, and RO2·. The main sequences of transformation of these radicals were established. The oxidative destruction of the artemisinin peroxy derivatives generates radicals RO2·, HO·, and HO2· in an amount of 4.5 radicals per peroxide derivative molecule on the average. The kinetic scheme of oxidative transformations of the hydroperoxide with four OOH groups and radicals formed from it was constructed using this radical as an example.

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Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432 Chernogolovka, Moscow Region, Russian Federation

    S. L. Solodova & E. T. Denisov

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  1. S. L. Solodova
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  2. E. T. Denisov
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Correspondence to E. T. Denisov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 760-768, April, 2009.

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Solodova, S.L., Denisov, E.T. Reactions of alkoxy and peroxy radicals formed upon the decomposition of hydroxyperoxide groups in the artemisinin derivatives. Russ Chem Bull 58, 777–785 (2009). https://doi.org/10.1007/s11172-009-0094-3

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  • DOI: https://doi.org/10.1007/s11172-009-0094-3

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