Reactivity and detailed reaction mechanism of quasi-tetrahedral o-azophenylboronic acid
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−.
Open Research
DATA AVAILABILITY STATEMENT
The data that supports the findings of this study are available in the supplementary material of this article.
