Reaction between 2,2-diphenyl-1-picrylhydrazyl and phenols. Substituent and solvent effects.
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概要
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A kinetic study has been made of the reaction between 2,2-diphenyl-1-picrylhydrazyl and phenols in various solvents. Polar effects in the rate-determining transition state are discussed in terms of the Hammett type relationship. Remarkable solvation effects were observed. For <I>p</I>-methoxyphenol the reaction rate is the greatest in the solvents which do not form strong H-bond with phenols, and the smallest in aprotic H-accepting solvents. For <I>o</I>-methoxyphenol the rate is the greatest in protic solvents. The results are interpreted in terms of the difference in the mode of hydrogen bondings. The rate for the reaction of the radical with α-naphthol was followed in dioxane–2,2,4-trimethylpentane mixtures. The results are explained by the theory of Kondo and Tokura, indicating that the free energy depression in the ground state takes place mainly through hydrogen bonding.
- 公益社団法人 日本化学会の論文
著者
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Nishimura Norio
Department Of Chemistry Faculty Of Science Okayama University
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Watanabe Toshihiko
Department Of Aeronautics And Astronautics University Of Tokyo
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Okino Yoshiko
Department of Chemistry, Faculty of Science, Okayama University
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Moriya Toshimichi
Department of Chemistry, Faculty of Science, Okayama University
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Tanabe Kazue
Department of Chemistry, Faculty of Science, Okayama University
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Kawabata Kimio
Department of Chemistry, Faculty of Science, Okayama University
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