Studies on Organosulfur Compounds. XIII. The Substituent Effect on the Acid Dissociation of Thioanilides and on the Rate of Oxidation by Hydrogen Peroxide

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概要

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• 2-Thiopicolinoanilide and its meta-and para-substituted derivatives were synthesized. These thioanilides were converted readily to the corresponding O-amides by hydrogen peroxide in alkaline solution. The oxidations of the thiopicolinoanilides by use of a large excess of hydrogen peroxide were kinetically carried out and the activation energies were determined. The small increase in the rates is attributed primarily to the electron-attracting effect of the substituents. On the other hand, these acid dissociation constants were measured in 20% ethanol-water at 20° by spectrophotometry and fitted the Hammett equation with the use of σ (ρ=1.4), but the p-carboethoxy group deviates from the straight line because of its much lower pK_a (8.42) value. In the reaction between 2-thiopicolinoanilides and o-aminophenol, the yield of 2-(2-pyridyl) benzoxazole increased with increasing electron-attracting effect of the substituent in the order of the observed acidity of thioanilides.

• 社団法人日本薬学会の論文
• 1976-07-25

著者

• 市川 正孝

  福山大学薬学部

• 市川 正孝

  Faculty Of Pharmaceutical Sciences Kumamoto Univerisity

• 久野 拓造

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 久野 拓三

  熊本大学薬学部

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