Reactivity and detailed reaction mechanism of quasi-tetrahedral o-azophenylboronic acid

IF 1.5 4区 化学 Q4 CHEMISTRY, PHYSICAL International Journal of Chemical Kinetics Pub Date : 2024-05-03 DOI:10.1002/kin.21726
Azusa Kuroda, Yota Suzuki, Yoshihisa Shintani, Tomoaki Sugaya, Koji Ishihara
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Abstract

Quasi-tetrahedral o-azophenylboronic acid (azoB-ROH), which contains the protic solvent ROH, is a key species in the colorimetric sensing of saccharides by o-azophenylboronic acid (azoB). In this study, we compared the reactivity of azoB-ROH with that of trigonal azoB and tetrahedral o-azophenylboronate (azoB-OH), and clarified the reaction mechanism of azoB-ROH with cis-1,2-cyclopentanediol and D-glucose. Analysis of the kinetics of the reactions of azoB with cis-1,2-cyclopentanediol and D-glucose in DMSO:water = 1:9 and azoB with cis-1,2-cyclopentanediol in tetrahydrofuran containing a small amount of methanol revealed that there was not much difference in the reactivity of azoB-H2O and azoB-OH, although the reactivity of azoB was higher than that of azoB-MeOH, that is, the reaction mechanism of azoB-H2O was essentially the same as that of azoB-OH.

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准四面体邻氮苯硼酸的反应活性和详细反应机理
含有原生溶剂 ROH 的准四面体邻氮苯硼酸(azoB-ROH)是邻氮苯硼酸(azoB)对糖类进行比色感应的关键物种。本研究比较了偶氮B-ROH与三方偶氮B和四面体邻氮苯硼酸(偶氮B-OH-)的反应活性,阐明了偶氮B-ROH与顺式-1,2-环戊二醇和D-葡萄糖的反应机理。分析了偶氮B与顺式-1,2-环戊二醇和 D-葡萄糖在 DMSO:water = 1:9 和含有少量甲醇的四氢呋喃中,偶氮 B 与顺式-1,2-环戊二醇和 D-葡萄糖的反应动力学分析表明,偶氮 B-H2O 和偶氮 B-OH- 的反应活性差别不大,但偶氮 B 的反应活性高于偶氮 B-MeOH,即偶氮 B-H2O 与偶氮 B-OH- 的反应机理基本相同。
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来源期刊
CiteScore
3.30
自引率
6.70%
发文量
74
审稿时长
3 months
期刊介绍: As the leading archival journal devoted exclusively to chemical kinetics, the International Journal of Chemical Kinetics publishes original research in gas phase, condensed phase, and polymer reaction kinetics, as well as biochemical and surface kinetics. The Journal seeks to be the primary archive for careful experimental measurements of reaction kinetics, in both simple and complex systems. The Journal also presents new developments in applied theoretical kinetics and publishes large kinetic models, and the algorithms and estimates used in these models. These include methods for handling the large reaction networks important in biochemistry, catalysis, and free radical chemistry. In addition, the Journal explores such topics as the quantitative relationships between molecular structure and chemical reactivity, organic/inorganic chemistry and reaction mechanisms, and the reactive chemistry at interfaces.
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