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Effect of the solvent composition in methanol-pentane and methanol-acetonitrile mixtures on the quantum yield of proton transfer and reactions of transient species in the photolysis of 2,2,4,6-tetramethyl-1,2-dihydroquinoline

  • Photochemistry
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Abstract

The photolysis of 2,2,4,6-tetramethyl-1,2-dihydroquinoline in binary MeOH-C5H12 and MeOH-MeCN mixtures was studied in dependence on the solvent composition by steady state and pulse photolysis. The photoinduced proton transfer from the N-H bond to the C(3) carbon atom of the heterocycle does not occur up to the methanol concentration of 0.25 (1 vol %) and 2.5 mol l−1 (10 vol %) in the MeOH-C5H12 and MeOH-MeCN mixtures, respectively. The trends in the increase in the relative quantum yield of the proton transfer reaction (Q mix/Q MeOH) and the decay rate constant for 2,2,4,6-tetramethyl-2,3-dihydroquinoline, the product of the proton transfer reaction, in dependence on the composition differ significantly for these binary mixtures. The results are interpreted in terms of peculiarities in the aggregation of methanol and the distribution of the DHQ molecules and transient species in the mixtures.

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References

  1. Itoh, M., Adachi, T., and Tokumura, K., J. Am. Chem. Soc., 1984, vol. 106, p. 850.

    Article  CAS  Google Scholar 

  2. Nakagawa, T., Kohtani, S., and Itoh, M., J. Am. Chem. Soc., 1995, vol. 117, p. 7952.

    Article  CAS  Google Scholar 

  3. Konijnenberg, J., Ekelmans, G.B., Huizer, A.H., and Varma, C.A.G.O., J. Chem. Soc., Faraday Trans. 2, 1989, vol. 85, p. 39.

    Article  CAS  Google Scholar 

  4. Munoz, M.A., Carmona, C., and Balon, M., Chem. Phys. Lett., 2004, vol. 393, p. 217.

    Article  CAS  Google Scholar 

  5. Pérez-Lustres, J.L., Rodriguez-Prieto, F., Mosquera, M., Senyushkina, T.A., Ernsting, N.P., and Kovalenko, S.A., J. Am. Chem. Soc., 2007, vol. 129, p. 5408.

    Article  Google Scholar 

  6. Nekipelova, T. Photochem., Photobiol. Sci., 2002, vol. 1, p. 204.

    Article  CAS  Google Scholar 

  7. Nekipelova, T.D. and Shishkov, V.S., Khim. Vys. Energ., 2004, vol. 38, no. 5, p. 355 [High Energy Chem., 2004, vol. 38, no. 5, p. 315].

    Google Scholar 

  8. Nekipelova, T.D. and Kuzmin, V.A., Khim. Vys. Energ., 2005, vol. 39, no. 6. p. 449 [High Energy Chem., 2005, vol. 39, no. 6, p. 392].

    Google Scholar 

  9. Nekipelova, T., Gostev, F., Kuzmin, V., and Sarkisov, O., Photochem. Photobiol. Sci., 2006, vol. 5, p. 815.

    Article  CAS  Google Scholar 

  10. Nekipelova, T.D., Malkin, Ya.N., and Kuzmin, V.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1980, no. 1, p. 80 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1980, vol. 29, no. 1, p. 80].

  11. Malkin, Ya.N., Pirogov, N.O., and Kuzmin, V.A., J. Photochem., 1984, vol. 26, p. 193.

    Article  CAS  Google Scholar 

  12. Nekipelova, T. and Kuzmin, V.A., Abstracts of Papers, 23 Int. Conf. on Photochemistry (ICP2007) Cologne: 2007, p. 206.

  13. Nekipelova, T.D., Proceedings of the International Symposium “Physics and Chemistry of Processes Oriented toward Development of New High Technologies, Materials, and Equipment”, Chernogolovka: 2007, p. 228.

  14. Gordon, A.J. and Ford, R.A., The Chemist Companion. A Handbook of Practical Data, Techniques and Reference Data, New York: Wiley, 1972.

    Google Scholar 

  15. Nekipelova, T.D., Kurkovskaya, L.N., Levina, I.I., Klyuev, N.A., and Kuzmin, V.A., Izv. Akad. Nauk, Ser. Khim., 1999, no. 11, p. 2072 [Russ. Chem. Bull., 1999, vol. 48, no. 11, p. 2049].

  16. Sastry, N.V. and Valand, M.K., J. Chem. Eng. Data., 1998, vol. 43, no. 2, p. 152.

    Article  CAS  Google Scholar 

  17. Nekipelova, T.D., Kuzmin, V.A., Razumov, V.F., and Gak, V.Yu., Khim. Vys. Energ., 2009, vol. 43, no. 5, p. 445 [High Energy Chem., 2009, vol. 43, no. 5. p. 391].

    Google Scholar 

  18. Enomoto, S., Miyazaki, M., Fujii, A., and Mukami, N., J. Phys. Chem. A., 2005, vol. 109, p. 9471.

    Article  CAS  Google Scholar 

  19. Meuwly, M., Bach, A., and Leutwyler, S., J. Am. Chem. Soc., 2001, vol. 123, p. 11446.

    Article  CAS  Google Scholar 

  20. Barreto, R.C., Coutinho, K., Georg, H.C., and Canuto, S., Phys. Chem. Chem. Phys., 2009, vol. 11, p. 1388.

    Article  CAS  Google Scholar 

  21. Durov, V.A., Iglesias, T.P., Shilov, I.Yu., and Moscalets, A.P., J. Mol. Liq., 2008, vol. 138, no. 1, p. 40.

    Article  CAS  Google Scholar 

  22. Stubbs, J.M. and Siepmann, J.I., J. Am. Chem. Soc., 2005, vol. 127, no. 13, p. 4722.

    Article  CAS  Google Scholar 

  23. Reimers, J.R. and Hall, L.E., J. Am. Chem. Soc., 1999, vol. 121, no. 15, p. 3730.

    Article  CAS  Google Scholar 

  24. Farwaneh, S.S., Yarwood, J., Cabaco, M.I., and Besnard, M., J Mol. Liq., 1993, vol. 56, p. 317.

    Article  CAS  Google Scholar 

  25. Gordon, J.E., The Organic Chemistry of Electrolyte Solutions, New York: Wiley, 1975.

    Google Scholar 

  26. Lygo, O.N., Nekipelova, T.D., and Khodot, E.N., Kinet. Katal., 2009, vol. 50, no. 3, p. 411 [Kinet. Catal., 2009, vol. 50, no. 3, p. 390].

    Article  Google Scholar 

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  1. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, ul. Kosygina 4, Moscow, 119334, Russia

    T. D. Nekipelova

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Correspondence to T. D. Nekipelova.

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Original Russian Text © T.D. Nekipelova, 2010, published in Khimiya Vysokikh Energii, 2010, Vol. 44, No. 4, pp. 319–325.

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Nekipelova, T.D. Effect of the solvent composition in methanol-pentane and methanol-acetonitrile mixtures on the quantum yield of proton transfer and reactions of transient species in the photolysis of 2,2,4,6-tetramethyl-1,2-dihydroquinoline. High Energy Chem 44, 290–296 (2010). https://doi.org/10.1134/S0018143910040065

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  • DOI: https://doi.org/10.1134/S0018143910040065

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