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Effect of the substituent position at the heterocycle on proton transfer from alcohols to the excited molecules of 1,2-dihydroquinolines

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Abstract

A novel compound 1,2,2,3-tetramethyl-1,2-dihydroquinoline (1223TMDQ) was synthesized, and the products of its steady-state photolysis in water, MeOH, EtOH, trifluoroethanol (TFE), PrnOH, and BuiOH were analyzed by 1H NMR and mass-spectrometry. The corresponding adducts with water and alcohols were identified. The presence of the adducts for alcohols with a number of carbon atoms n > 1 distinguishes 1223TMDQ from 2,2,4-trimethyl-1,2-dihydroquinolines with methyl-, alkoxy-, and hydroxy-substituents at positions 1, 6, and 8, for which the formation of adducts was observed only in the presence of water and MeOH. The results were interpreted in terms of the effect of steric hindrance caused by substituents in the heterocycle and increasing size of the alkyl group of alcohol on proton transfer from a solvent to the molecule of 1,2-dihydroquinoline, which occurs in the complex between the solvent and the dihydroquinoline molecule in the excited singlet state. It was shown that the main steric hindrance for the photoinduced proton transfer in 2,2,4-substituted 1,2-dihydroquinolines is the substituent at position C(4) of the heterocycle.

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Authors and Affiliations

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

    O. N. Lygo, T. D. Nekipelova, V. S. Kurova & V. A. Kuz’min

  2. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninskii pr. 47, Moscow, 119991, Russia

    E. N. Khodot & S. I. Firgang

Authors
  1. O. N. Lygo
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  2. E. N. Khodot
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  3. T. D. Nekipelova
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  4. V. S. Kurova
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  5. V. A. Kuz’min
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  6. S. I. Firgang
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Correspondence to T. D. Nekipelova.

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Original Russian Text © O.N. Lygo, E.N. Khodot, T.D. Nekipelova, V.S. Kurova, V.A. Kuz’min, S.I. Firgang, 2010, published in Khimiya Vysokikh Energii, 2010, Vol. 44, No. 3, pp. 217–223.

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Lygo, O.N., Khodot, E.N., Nekipelova, T.D. et al. Effect of the substituent position at the heterocycle on proton transfer from alcohols to the excited molecules of 1,2-dihydroquinolines. High Energy Chem 44, 189–195 (2010). https://doi.org/10.1134/S0018143910030069

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  • DOI: https://doi.org/10.1134/S0018143910030069

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