Affiliation:
1. Department of Chemistry and Biochemistry School of Advanced Science and Engineering Waseda University, Okubo Shinjuku‐ku Tokyo Japan
2. Graduate School of Science and Engineering Saitama University Saitama Japan
3. Education Center Faculty of Engineering Chiba Institute of Technology Narashino Chiba Japan
Abstract
AbstractQuasi‐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−.