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Photochemistry of N-substituted salicylic acid amides

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Abstract

The products of photolysis of N-substituted salicylic acid amides, viz., 2-hydroxy-3-tert-butyl-5-ethylbenzoic acid N-(4-hydroxy-3,5-di-tert-butylphenyl)amide (1) and 2-hydroxybenzoic acid N-[3-(4-hydroxy-3,5-di-tert-butylphenyl)prop-1-yl]amide (2), in heptane were studied by optical spectroscopy and stationary and nanosecond laser photolysis (Nd: YAG laser, 355 nm). It was shown by the method of partial deuteration of amides 1 and 2 that they exist in both the unbound state and as complexes with intraand intermolecular hydrogen bond. Amides 1 and 2 are subjected to photolysis, which results in the formation of a triplet state and phenoxyl radicals RO• presumably due to the absorption of the second photon by the excited singlet state. The formation of radical products due to N–H bond ionization was not observed. The main channel of decay of the triplet state and radicals RO• is triplet–triplet annihilation and recombination (k r ≈ 2.3•108 L mol–1 s–1), respectively. The UV irradiation of compounds 1 and 2 leads to the excitation of the amide groups, and no formation of radical products due to N–H bond ionization was observed.

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Authors and Affiliations

  1. Institute of Chemical Kinetics and Combustion, Siberian Branch, Russian Academy of Sciences, 3 ul. Institutskaya, 630090, Novosibirsk, Russian Federation

    I. P. Pozdnyakov, V. F. Plyusnin & V. P. Grivin

  2. Tyumen State Medical University, Ministry of Health of the Russian Federation, 54 ul. Odesskaya, 625023, Tyumen, Russian Federation

    N. M. Storozhok & N. P. Medyanik

  3. Tyumen State University, 10 ul. Semakova, 625003, Tyumen, Russian Federation

    S. A. Krekov & V. E. Borisenko

  4. Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 9 prosp. Akad. Lavrent´eva, 630090, Novosibirsk, Russian Federation

    A. P. Krysin

Authors
  1. I. P. Pozdnyakov
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  2. N. M. Storozhok
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  3. N. P. Medyanik
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  4. S. A. Krekov
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  5. V. E. Borisenko
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  6. A. P. Krysin
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  7. V. F. Plyusnin
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  8. V. P. Grivin
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Correspondence to N. M. Storozhok.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1319–1326, June, 2015.

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Pozdnyakov, I.P., Storozhok, N.M., Medyanik, N.P. et al. Photochemistry of N-substituted salicylic acid amides. Russ Chem Bull 64, 1319–1326 (2015). https://doi.org/10.1007/s11172-015-1012-5

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  • DOI: https://doi.org/10.1007/s11172-015-1012-5

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