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Solvent effects on the tautomerization, autoxidation and bond-exchange reactions of 2-mercaptopyridine derivatives
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- Furutani Masahiro
- Department of Chemistry and Biology, National Institute of Technology
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- Sakaguchi Motoya
- Department of Chemistry and Biology, National Institute of Technology
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- Sasa Kazuhiro
- Department of Chemistry and Biology, National Institute of Technology
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Description
<p>Tautomerization, autoxidation and bond-exchange reactions of 2-mercaptopyridine derivatives were investigated in solution, by using several kinds of solvents. A 2-mercaptopyridine derivative having an N-benzylamide group was dissolved not only in water but also in cyclohexane, although the solubility toward such solvents was lower than that toward methanol or chloroform. From the UV-Vis spectra, it was confirmed that thione-type isomer was major in these solvents except for cyclohexane. Autoxidation reactions were monitored in methanol or methanol-d4, and ca. 36% of 2-mercaptopyridyl groups were oxidized into disulfide bonds within a month in 1H-NMR spectral measurements. Bond-exchange reactions between 2,2’-dipyridyl disulfide and a thiol compound were observed more clearly in methanol than in chloroform, suggesting a solvent effect to dissolution of corresponding disulfide compounds.</p>
Journal
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- MATERIAL TECHNOLOGY
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MATERIAL TECHNOLOGY 40 (3), 16-22, 2022-06-25
Japan Research Institute of Materials Technology