Methylation of a benzene ring as a chemical signal. Marked changes in the pattern of temperature dependence of the selectivity in oxidation of a pair of associating thiols.

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概要

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• Temperature dependence of the selectivity [the ratio of an unsymmetrical disulfide to symmetrical one] has been studied in oxidation of a pair of associating thiols, each with the recognition site [C<SUB>6</SUB>H<SUB>4</SUB>N(CH<SUB>3</SUB>)<SUB>2</SUB> and R<SUP>1</SUP>], with O<SUB>2</SUB> in 80% (v/v) acetonitrile–20% water in the range of −10 to 70 °C. The selectivity for R<SUP>1</SUP>=C<SUB>6</SUB>H<SUB>4</SUB>CH<SUB>3</SUB> shows a minimum at 35 °C, whereas for R<SUP>1</SUP>=C<SUB>6</SUB>H<SUB>5</SUB> the selectivity exhibits a maximum at 35 °C; for R<SUP>1</SUP>=C<SUB>6</SUB>H<SUB>4</SUB>C<SUB>2</SUB>H<SUB>5</SUB> plots of the selectivity against temperature shows a sigmoid-like curve. The selectivity in oxidation of a pair of non-associating thiols, 2-(dimethylamino)ethanethiol and a para-substituted benzenethiol, remains practically unaltered with temperature in the same solvent. Though thiol-disulflde exchange reaction proceeds slowly below 35 °C, the selectivity in the exchange differs entirely from that in the oxidation. It has been found that changes in hydrophobicity with R<SUP>1</SUP> and temperature cannot explain dramatic alterations in the selectivity with R<SUP>1</SUP> and temperature.

• 公益社団法人 日本化学会の論文

著者

• Endo Tadashi

  Department Of Applied Chemistry Faculty Of Engineering Tohoku University

• NAKAGAWA Naoya

  The University of Electro Communications

• Kaneko Yuji

  Department Of Chemistry University Of Tsukuba

• Kamei Shinichi

  Kyowa Kagaku Co., Ltd.

• Okubo Akihiro

  Department of Chemistry, College of Science and Engineering, Aoyama Gakuin University

• Uehara Masatoshi

  Department of Chemistry, College of Science and Engineering, Aoyama Gakuin University

• Tasai Hidetoshi

  Department of Chemistry, College of Science and Engineering, Aoyama Gakuin University

• Sato Akiyoshi

  Department of Chemistry, College of Science and Engineering, Aoyama Gakuin University

• Nikki Kunio

  The University of Electro-communications

• Endo Tadashi

  Department of Chemistry, College of Science and Engineering, Aoyama Gakuin University

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