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Study of Methylbenzylthione Photoreaction Using Chemically Induced Nuclear Polarization

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Abstract

The mechanisms of photoreactions of methylbenzylthione PhCH2CSCH3 (1) were studied by NMR spectroscopy with chemically induced dynamic nuclear polarization (CIDNP). It was established from the sign of 13C and 1H CIDNP that polarization occurs during the decay of excited thioketones in the triplet state. The elementary acts of the reaction and intermediate compounds were proved. It was found that photolysis of thione (1) is a Norrish type I reaction with predominant recombination in the radical pair and regeneration of the starting thioketone.

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REFERENCES

  1. A. L. Buchachenko, R. Z. Sagdeev, and K. M. Salikhov, Magnetic and Spin Effects in Chemical Reactions (Nauka, Novosibirsk, 1978) [in Russian].

    Google Scholar 

  2. Chemistry of Organic Sulfur Compounds. General Issues, Ed. by L. I. Belen’kii (Khimiya, Moscow, 1988), p. 329 [in Russian].

    Google Scholar 

  3. I. I. Kondror, Doctoral (Chem.) Dissertation (Nesmeyanov Inst. of Organoelement Compounds, Acad. Sci. SSSR, Moscow, 1985).

  4. A. degl’Innocenti, A. Capperucci, A. Mordini, G. Reginata, and F. Ricci, Tetrahedron Lett., No. 34, 873 (1993).

  5. A. Ishii, M. Hoshimo, and K. Nakayama, Pure Appl. Chem., No. 68, 869 (1996).

  6. E. Block, T. Bayer, S. Naganathan, and S. Zhao, J. Am. Chem. Soc., No. 118, 2799 (1996).

  7. Yu. L. Frolov, L. M. Sinegovskaya, V. V. Keiko, et al., Russ. Chem. Bull. 35, 1811 (1986).

    Article  Google Scholar 

  8. Yu. L. Frolov, L. M. Sinegovskaya, V. V. Keiko, et al., Russ. Chem. Bull. 35, 1811 (1986).

    Article  Google Scholar 

  9. Yu. L. Frolov, L. M. Sinegovskaya, N. K. Gusarova, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1780 (1985).

  10. Zong-Ying Liu, Jiun-Wei Hu, Chun-Hao Huang, et al., J. Am. Chem. Soc. 141, 9885 (2019).

    Article  PubMed  CAS  Google Scholar 

  11. S. Lévesque, D. Gendron, N. Bérubé, et al., J. Phys. Chem. C 118, 3953 (2014).

    Article  Google Scholar 

  12. N. Jayaraj, M. V. S. N. Maddipatla, R. Prabhakar, et al., J. Phys. Chem. B 114, 14320 (2010).

    Article  PubMed  CAS  Google Scholar 

  13. M. Szymanski, J. Phys. Chem. A 102, 677 (1998).

    Article  CAS  Google Scholar 

  14. A. K. Newman, A. M. Henry, J. P. Madriaga, et al., Photochem. Photobiol. Sci. 21, 303 (2022).

    Article  PubMed  CAS  Google Scholar 

  15. J. D. Coyle, Tetrahedron, No. 41, 5393 (1985).

  16. V. I. Porkhun and Yu. V. Aristova, Russ. Chem. Bull. 68, 565 (2019).

    Article  CAS  Google Scholar 

  17. T. V. Leshina and N. E. Polyakov, J. Phys. Chem. 94, 4379 (1990).

    Article  CAS  Google Scholar 

  18. V. I. Porkhun, Yu. V. Aristova, and I. V. Sharkevich, Russ. J. Phys. Chem. A 91, 1358 (2017).

    Article  CAS  Google Scholar 

  19. V. I. Porkhun, Yu. V. Aristova, and I. L. Gonik, Russ. J. Phys. Chem. A 92, 2092 (2018).

    Article  CAS  Google Scholar 

  20. V. I. Porkhun and A. I. Rakhimov, Russ. J. Phys. Chem. A 86, 1915 (2012).

    Article  CAS  Google Scholar 

  21. A. V. Yurkovskaya, H. M. Vieth, and K. L. Ivanov, J. Phys. Chem. (2015). https://doi.org/10.1021/acs.jpcb.5b03032

  22. Wang Yun, Yan Bao, and Wang Ting, Chin. Chem. Lett., No. 14, 270 (2003).

  23. K. D. Atkinson, M. J. Cowley, P. I. P. Elliott, et al., J. Am. Chem. Soc., No. 131, 1336 (2009).

  24. V. I. Porkhun, Yu. V. Aristova, and I. L. Gonik, Russ. Chem. Bull. 67, 1364 (2018).

    Article  CAS  Google Scholar 

  25. V. I. Porkhun, Izv. Vyssh. Uchebn. Zaved., Priborostr. 53 (10), 65 (2010).

    Google Scholar 

  26. J. Calvert and J. Pitts, Photochemistry (Wiley, New York, 1967).

    Google Scholar 

  27. A. L. Buchachenko and A. M. Wasserman, Stable Radicals (Khimiya, Moscow, 1973) [in Russian].

    Google Scholar 

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Correspondence to N. A. Kuznetsova.

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Translated by L. Smolina

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Porkhun, V.I., Kuznetsova, N.A., Podoprigora, A.G. et al. Study of Methylbenzylthione Photoreaction Using Chemically Induced Nuclear Polarization. Russ. J. Phys. Chem. 96, 2547–2550 (2022). https://doi.org/10.1134/S0036024422110243

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  • DOI: https://doi.org/10.1134/S0036024422110243

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