スガヤ　トモアキ   Tomoaki Sugaya   菅谷　知明    所属   千葉工業大学  工学部 教育センター（工学部）    職種   教授
言語種別	英語
発行・発表の年月	2020/01
形態種別	学術雑誌
査読	査読あり
標題	Reactivity of Boronic Acids toward Catechols in Aqueous Solution
執筆形態	共著
掲載誌名	The Journal of organic chemistry
掲載区分	国外
出版社・発行元	American Chemical SOciety
著者・共著者	Yota Suzuki, Daisuke Kusuyama, Tomoaki Sugaya, Satoshi Iwatsuki, Masahiko Inamo, Hideo D. Takagi, Koji Ishihara
概要	Fundamental information on the reactivities of boronic acids toward catechols in aqueous solution is required in all the fields dealing with boronic acid. However, comprehensive studies on reactivity are often hindered by so-called "proton ambiguity," which makes it impossible for the rate constants of boronic acid and boronate ion to be determined separately. Herein, we set up two reaction systems without proton ambiguity: (1) Alizarin Red S and (2) Tiron with several boronic acids (RB(OH)2) with different pKas and performed kinetic and equilibrium studies on the reaction systems. It was shown that the logarithms of the rate constants of RB(OH)2 and its conjugate boronate ion (RB(OH)3-) decreased and increased linearly, respectively, with increasing pKa of RB(OH)2 for both systems. Consequently, the reactivities of RB(OH)2 and RB(OH)3- were reversed at high RB(OH)2 pKa.
DOI	10.1021/acs.joc.9b03326
ISSN	1520-6904
PMID	32003994