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 | |
| Publication status | Accepted/In press - 2015 May 31 |
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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
Reaction mechanism of diphenylborinic acid with d-fructose in aqueous solution. / Sobue, Yukika; Sugaya, Tomoaki; Iwatsuki, Satoshi; Inamo, Msahiko; Takagi, Hideo D.; Odani, Akira; Ishihara, Koji.
In: Journal of Molecular Liquids, 31.05.2015.Research output: Contribution to journal › Article
}
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 -