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Laser flash photolysis studies on radical formation by H-atom abstraction of triplet vitamin K3 and by H-atom transfer via the triplet exciplex between triplet methyldihydroxynaphthalene and benzophenone

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Abstract

Nanosecond laser photolysis techniques were incorporated to obtain (1) the absorption spectra and coefficients of triplet vitamin K3 (2-methyl-1,4-naphthoquinone, MNQ) and its ketyl radical (2-methylnaphthosemiquinone, 2MNQH*) in acetonitrile (ACN) as well as to reveal (2) the mechanisms for hydrogen atom abstraction of triplet MNQ (3MNQ*) from phenol which proceeded in a diffusion process with an efficiency of unity. On the other hand, the hydroxymethylnaphthoxy radical was produced with the benzophenone ketyl radical (BPK) by the hydrogen atom transfer from triplet 2-methyl-1,4-dihydroxynaphthalene (MDHNp) sensitized by triplet benzophenone to benzophenone (BP) via the triplet exciplex. The question to be addressed was, which was produced in the MDHNp-BP system, the 2-methyl or 3-methylnaphthosemiquinone radical? Comparing the absorption spectrum and coefficient of the radical produced via the triplet exciplex with those of the 2MNQH* obtained by H-atom abstraction of 3MNQ*, the radical formed with BPK was revealed to be 2MNQH*. The reasons for the preferable formation of 2MNQH* are discussed for H-atom abstraction as well as the transfer reactions.

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Authors and Affiliations

  1. Department of Chemistry, Gunma University, Kiryu, 376, Gunma, Japan

    H. Shizuka

  2. Eisai Chemical Co., Ltd., Hasaki, Kashima-gun, 341-02, Ibaraki, Japan

    I. Amada

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  1. I. Amada
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  2. M. Yamaji
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  3. M. Sase
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  4. H. Shizuka
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Amada, I., Yamaji, M., Sase, M. et al. Laser flash photolysis studies on radical formation by H-atom abstraction of triplet vitamin K3 and by H-atom transfer via the triplet exciplex between triplet methyldihydroxynaphthalene and benzophenone. Res. Chem. Intermed. 23, 121–134 (1997). https://doi.org/10.1163/156856797X00277

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  • DOI: https://doi.org/10.1163/156856797X00277

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