Reaction mechanism of diphenylborinic acid with d-fructose in aqueous solution

Yukika Sobue; Tomoaki Sugaya; Satoshi Iwatsuki; Msahiko Inamo; Hideo D. Takagi; Akira Odani; Koji Ishihara

doi:10.1016/j.molliq.2015.07.062

Reaction mechanism of diphenylborinic acid with d-fructose in aqueous solution

Yukika Sobue, Tomoaki Sugaya, Satoshi Iwatsuki, Msahiko Inamo, Hideo D. Takagi, Akira Odani, Koji Ishihara

Research output: Contribution to journal › Article

4 Citations (Scopus)

Abstract

The reaction of d-fructose with diphenylborinic acid (Ph<inf>2</inf>B(OH)), to which d-fructose cannot coordinate tridentately, was kinetically investigated in order to solve the reaction mechanism, and to find a clue to resolve the two-step reaction mechanism of boronic acid (RB(OH)<inf>2</inf>) with d-fructose. The title reaction was a single-step reaction under the pseudo first-order conditions with large excess d-fructose over Ph<inf>2</inf>B(OH), which suggests that the reaction of RB(OH)<inf>2</inf> with d-fructose consists of the fast formation of a two-coordinate complex followed by the slow formation of a three-coordinate complex. The kinetic reactivity of Ph<inf>2</inf>B(OH) was considerably higher than that of its conjugate base, diphenylborinate ion (Ph<inf>2</inf>B(OH)<inf>2</inf> <sup>-</sup>). It was shown that Ph<inf>2</inf>B(OH)<inf>2</inf> <sup>-</sup> interacted with CHES buffer to form an outer-sphere complex, whereas no interaction was observed between Ph<inf>2</inf>B(OH) and CHES buffer. Both the free borinate ion and the restrained borinate ion into the outer-sphere complex react with d-fructose to form the chelate complex via stable binary and ternary outer-sphere complexes, respectively.

Original language	English
Journal	Journal of Molecular Liquids
DOIs	https://doi.org/10.1016/j.molliq.2015.07.062
Publication status	Accepted/In press - 2015 May 31

Fingerprint

Keywords

Borinic acid
d-Fructose
Reaction mechanism

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Spectroscopy
Condensed Matter Physics
Atomic and Molecular Physics, and Optics
Electronic, Optical and Magnetic Materials
Materials Chemistry

Cite this

Sobue, Y., Sugaya, T., Iwatsuki, S., Inamo, M., Takagi, H. D., Odani, A., & Ishihara, K. (Accepted/In press). Reaction mechanism of diphenylborinic acid with d-fructose in aqueous solution. Journal of Molecular Liquids. https://doi.org/10.1016/j.molliq.2015.07.062

@article{3f1356aff0aa417ebc875a6765535bc9,

title = "Reaction mechanism of diphenylborinic acid with d-fructose in aqueous solution",

abstract = "The reaction of d-fructose with diphenylborinic acid (Ph2B(OH)), to which d-fructose cannot coordinate tridentately, was kinetically investigated in order to solve the reaction mechanism, and to find a clue to resolve the two-step reaction mechanism of boronic acid (RB(OH)2) with d-fructose. The title reaction was a single-step reaction under the pseudo first-order conditions with large excess d-fructose over Ph2B(OH), which suggests that the reaction of RB(OH)2 with d-fructose consists of the fast formation of a two-coordinate complex followed by the slow formation of a three-coordinate complex. The kinetic reactivity of Ph2B(OH) was considerably higher than that of its conjugate base, diphenylborinate ion (Ph2B(OH)2 -). It was shown that Ph2B(OH)2 - interacted with CHES buffer to form an outer-sphere complex, whereas no interaction was observed between Ph2B(OH) and CHES buffer. Both the free borinate ion and the restrained borinate ion into the outer-sphere complex react with d-fructose to form the chelate complex via stable binary and ternary outer-sphere complexes, respectively.",

keywords = "Borinic acid, d-Fructose, Reaction mechanism",

author = "Yukika Sobue and Tomoaki Sugaya and Satoshi Iwatsuki and Msahiko Inamo and Takagi, {Hideo D.} and Akira Odani and Koji Ishihara",

year = "2015",

month = may

day = "31",

doi = "10.1016/j.molliq.2015.07.062",

language = "English",

journal = "Journal of Molecular Liquids",

issn = "0167-7322",

publisher = "Elsevier",

}

TY - JOUR

T1 - Reaction mechanism of diphenylborinic acid with d-fructose in aqueous solution

AU - Sobue, Yukika

AU - Sugaya, Tomoaki

AU - Iwatsuki, Satoshi

AU - Inamo, Msahiko

AU - Takagi, Hideo D.

AU - Odani, Akira

AU - Ishihara, Koji

PY - 2015/5/31

Y1 - 2015/5/31

N2 - The reaction of d-fructose with diphenylborinic acid (Ph2B(OH)), to which d-fructose cannot coordinate tridentately, was kinetically investigated in order to solve the reaction mechanism, and to find a clue to resolve the two-step reaction mechanism of boronic acid (RB(OH)2) with d-fructose. The title reaction was a single-step reaction under the pseudo first-order conditions with large excess d-fructose over Ph2B(OH), which suggests that the reaction of RB(OH)2 with d-fructose consists of the fast formation of a two-coordinate complex followed by the slow formation of a three-coordinate complex. The kinetic reactivity of Ph2B(OH) was considerably higher than that of its conjugate base, diphenylborinate ion (Ph2B(OH)2 -). It was shown that Ph2B(OH)2 - interacted with CHES buffer to form an outer-sphere complex, whereas no interaction was observed between Ph2B(OH) and CHES buffer. Both the free borinate ion and the restrained borinate ion into the outer-sphere complex react with d-fructose to form the chelate complex via stable binary and ternary outer-sphere complexes, respectively.

AB - The reaction of d-fructose with diphenylborinic acid (Ph2B(OH)), to which d-fructose cannot coordinate tridentately, was kinetically investigated in order to solve the reaction mechanism, and to find a clue to resolve the two-step reaction mechanism of boronic acid (RB(OH)2) with d-fructose. The title reaction was a single-step reaction under the pseudo first-order conditions with large excess d-fructose over Ph2B(OH), which suggests that the reaction of RB(OH)2 with d-fructose consists of the fast formation of a two-coordinate complex followed by the slow formation of a three-coordinate complex. The kinetic reactivity of Ph2B(OH) was considerably higher than that of its conjugate base, diphenylborinate ion (Ph2B(OH)2 -). It was shown that Ph2B(OH)2 - interacted with CHES buffer to form an outer-sphere complex, whereas no interaction was observed between Ph2B(OH) and CHES buffer. Both the free borinate ion and the restrained borinate ion into the outer-sphere complex react with d-fructose to form the chelate complex via stable binary and ternary outer-sphere complexes, respectively.

KW - Borinic acid

KW - d-Fructose

KW - Reaction mechanism

UR - http://www.scopus.com/inward/record.url?scp=84938718681&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84938718681&partnerID=8YFLogxK

U2 - 10.1016/j.molliq.2015.07.062

DO - 10.1016/j.molliq.2015.07.062

M3 - Article

AN - SCOPUS:84938718681

JO - Journal of Molecular Liquids

JF - Journal of Molecular Liquids

SN - 0167-7322

ER -

Access to Document

10.1016/j.molliq.2015.07.062