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 journalArticle

    3 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 languageEnglish
    JournalJournal of Molecular Liquids
    DOIs
    Publication statusAccepted/In press - 2015 May 31

    Fingerprint

    Fructose
    aqueous solutions
    acids
    Acids
    Ions
    Buffers
    buffers
    Boronic Acids
    ions
    chelates
    diphenylborinic acid
    reactivity
    Kinetics
    kinetics

    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 journalArticle

    Sobue, Yukika ; Sugaya, Tomoaki ; Iwatsuki, Satoshi ; Inamo, Msahiko ; Takagi, Hideo D. ; Odani, Akira ; Ishihara, Koji. / Reaction mechanism of diphenylborinic acid with d-fructose in aqueous solution. In: Journal of Molecular Liquids. 2015.
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    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.",
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    AU - Sugaya, Tomoaki

    AU - Iwatsuki, Satoshi

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    AU - Takagi, Hideo D.

    AU - Odani, Akira

    AU - Ishihara, Koji

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