Studies of Diazosulfides. I. A Kinetic Study of the Reaction of Diaryldiazosulfides with β-Naphthol in Alkaline Ethanol
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概要
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It was found that diaryldiazosulfides (I) reacted at an appreciable rate with β-naphthol in alkaline ethanol to produce azo-dyes. This is contrary to Hantzsch's observation. The initialrate constants of the reaction were determined at various temperatures. The electron-donating substituents accelerated the rate when they were in the <I>N</I>-aryl part of I (substituent X) but retarded when in the <I>S</I>-aryl part of I (substituent Y). A set of ρ-values which have opposite signs, ρ<SUB>x</SUB>=−2.96 and ρ<SUB>Y</SUB>=3.93, suggested that the rate-determining step in this reaction is the heterolytic rupture of the N-S bond of I. This was supported by the negative values of the entropy of activation and by such a solvent effect as that the rate was significantly increased when the polarity of the solvent increased. As the change in the concentration of β-naphthol affected the rate, the possibility of the participation of the transition state or of the intermediate including β-naphthol was also discussed.
- 公益社団法人 日本化学会の論文
著者
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Tanaka Nobuo
Department Of Agro-environmental Sciences Graduate School Of Bioresource And Bioenvironmental Scienc
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Yamada Takashi
Department Of Animal Science Graduate School Of Agricultural Science Kobe University
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Kaji Aritsune
Department of Chemistry, Faculty of Science, Kyoto University
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Morisawa Takao
Department of Chemistry, Faculty of Science, Kyoto University
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Nishikuri Masao
Department of Chemistry, Faculty of Science, Kyoto University
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