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Effect of Protonation on Ferrocenylmethanol Oxidation with p-Benzoquinone in the Presence of Perchloric Acid

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Abstract

The metal complex in the FcCH2OH–HClO4–p-benzoquinone system is oxidized with p-benzoquinone as well as with the hydrogen ion as a result of its protonation. Involvement of the acid in both processes determines their influence of each of them on the rate of the other one. This fact has been confirmed by the obtained dependences of the rate of ferrocenium ions accumulation during protonation and oxidation of FcCH2OH on the reactants concentrations as well as by the derived kinetic equations of the processes. The degree of their mutual influence depends on the solvating properties of the solvents and the ratio of the starting concentrations of the metal complex and the acid, which affect the yield of the FcC+H2 carbocation and its ability to redox isomerism upon protonation of the metal complex.

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REFERENCES

  1. Fomin, V.M. and Shirokov, A.E., Russ. J. Gen. Chem., 2009, vol. 89, no. 5, p. 928. https://doi.org/10.1134/S1070363209050119

    Article  CAS  Google Scholar 

  2. Fomin, V.M., Orlova, E.A., and Zaitseva, K.S., Russ. J. Gen. Chem., 2014, vol. 84, no. 4, p. 722. https://doi.org/10.1134/S1070363214040215

    Article  CAS  Google Scholar 

  3. Rinehart, K.L.Jr., Michejda, C.J., and Kittle, P.A., J. Am. Chem. Soc., 1959, vol. 81, p. 3162. https://doi.org/10.1021/ja01521a082

    Article  CAS  Google Scholar 

  4. Fomin, V.M., Kochetkova, E.S., and Klyuchevskii, K.V., Russ. J. Gen. Chem., 2018, vol. 88, no. 5. P 948. https://doi.org/10.1134/S1070363218050183

  5. Weinmayr, V., J. Am. Chem. Soc., 1955, vol. 77, p. 3009. https://doi.org/10.1021/ja01616a026

    Article  CAS  Google Scholar 

  6. Nesmeyanov, A.N., Sazonova, V.A., Drozd, V.N., and Rodionova, N.A., Dokl. Akad. Nauk SSSR, 1965, vol. 160, no. 2, p. 355.

    CAS  Google Scholar 

  7. Mat’e, Zh. and Paniko, R., Kurs teoreticheskikh osnov organicheskoi khimii (Course of Theoretical Foundations of Organic Chemistry), Moscow: Mir, 1975, p. 530.

  8. Bethel, D. and Gold, V., Carbonium Ions: An Introduction, London: Academic Press, 1967.

  9. Clark, W.M., Oxidation-Reduction Potentials in Organic Systems, Baltimore: Williams and Wilkins, 1960.

  10. Castagnola, M., Floris, B., and Illuminati, G., J. Organomet. Chem., 1973, vol. 60, no. 1, p. 17. https://doi.org/10.1016/S0022-328X(00)85420-0

    Article  Google Scholar 

  11. Energii razryva khimicheskikh svyazei. Potentsialy ionizatsii i srodstvo k elektronu (Energies of Breaking Chemical Bonds. Ionization Potentials and Electron Affinity), Kondrat’ev, V.N., Ed., Moscow: Nauka, 1974, p. 333.

  12. Bell, R.P., The Proton in Chemistry, Cornell University, 1958.

  13. Fomin, V.M., Markin, A.V., and Shuklina, N.N., Russ. J. Gen. Chem., 2020, vol. 90, no. 6, p. 994. https://doi.org/10.31857/S0044460X20060091

    Article  CAS  Google Scholar 

  14. Fomin, V.M., Shuklina, N.N., and Klimova, M.N., Russ. J. Phys. Chem., 2020, vol. 94, no. 9, p. 1791. https://doi.org/10.31857/S0044453720090071

    Article  Google Scholar 

  15. Kondo, T., Yamamoto, K., and Kumada, M., J. Organomet. Chem., 1972, vol. 35, no. 1, p. 30. https://doi.org/10.1016/S0022-328X(00)86870-9

    Article  Google Scholar 

  16. Kondo, T., Yamamoto, K., and Kumada, M., J. Organomet. Chem., 1973, vol. 61, no. 16, p. 1245. https://doi.org/10.1016/S0022-328X(00)86565-1

    Article  Google Scholar 

  17. Ashkenazi, P. and Catz, M., Angew. Chem., 1972, vol. 84, p. 1106. https://doi.org/10.1002/ange.19720842210

    Article  Google Scholar 

  18. Catz, M., Ashkenazi, P., Dani, S., Gottlieb, Y., J. Organomet. Chem., 1977, vol. 124, no. 1, p. 49. https://doi.org/10.1016/S0022-328X(00)90048-2

    Article  Google Scholar 

  19. Bitterwolf, T.E. and Ling, A.C., J. Organomet. Chem., 1971, vol. 40, no. 1, p. 29. https://doi.org/10.1016/S0022-328X(00)86974-0

    Article  Google Scholar 

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ACKNOWLEDGMENTS

The authors are grateful to Sinor company for the provided sample of ferrocenylmethanol.

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Authors and Affiliations

  1. N.I. Lobachevsky State University of Nizhny Novgorod, 603950, Nizhny Novgorod, Russia

    V. M. Fomin & N. N. Shuklina

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  1. V. M. Fomin
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  2. N. N. Shuklina
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Correspondence to V. M. Fomin.

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Translated from Zhurnal Obshchei Khimii, 2021, Vol. 91, No. 7, pp. 1078–1091 https://doi.org/10.31857/S0044460X2107012X.

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Fomin, V.M., Shuklina, N.N. Effect of Protonation on Ferrocenylmethanol Oxidation with p-Benzoquinone in the Presence of Perchloric Acid. Russ J Gen Chem 91, 1342–1353 (2021). https://doi.org/10.1134/S1070363221070124

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