Kinetic evidence for high reactivity of 3-nitrophenylboronic acid compared to its conjugate boronate ion in reactions with ethylene and propylene glycols

Chiaki Miyamoto, Kazunori Suzuki, Satoshi Iwatsuki, Masahiko Inamo, Hideo D. Takagi, Koji Ishihara

    Research output: Contribution to journalArticle

    25 Citations (Scopus)

    Abstract

    The rate constants for a boronate ion were determined for the first time using the reaction systems of 3-nitrophenylboronic acid (3-NO 2PhB(OH)2) with ethylene glycol (EG) and propylene glycol (PG) in an alkaline solution: the rate constants (25°C, I = 0.10 M) for the reactions of 3-NO2PhB(OH)3 - are 1.2 M -1 s-1 (EG) and 1.5 M-1 s-1 (PG), which are at least 103 times smaller than those for the reactions of 3-NO2PhB(OH)2 [1.0 × 104 M-1 s-1 (EG) and 5.8 × 103 M-1 s-1 (PG)].

    Original languageEnglish
    Pages (from-to)1417-1419
    Number of pages3
    JournalInorganic Chemistry
    Volume47
    Issue number5
    DOIs
    Publication statusPublished - 2008 Mar 3

    Fingerprint

    Ethylene Glycols
    Propylene Glycols
    Propylene Glycol
    Ethylene Glycol
    propylene
    glycols
    ethylene
    reactivity
    Ions
    acids
    Kinetics
    Rate constants
    kinetics
    ions
    3-nitrobenzeneboronic acid

    ASJC Scopus subject areas

    • Inorganic Chemistry

    Cite this

    Kinetic evidence for high reactivity of 3-nitrophenylboronic acid compared to its conjugate boronate ion in reactions with ethylene and propylene glycols. / Miyamoto, Chiaki; Suzuki, Kazunori; Iwatsuki, Satoshi; Inamo, Masahiko; Takagi, Hideo D.; Ishihara, Koji.

    In: Inorganic Chemistry, Vol. 47, No. 5, 03.03.2008, p. 1417-1419.

    Research output: Contribution to journalArticle

    Miyamoto, Chiaki ; Suzuki, Kazunori ; Iwatsuki, Satoshi ; Inamo, Masahiko ; Takagi, Hideo D. ; Ishihara, Koji. / Kinetic evidence for high reactivity of 3-nitrophenylboronic acid compared to its conjugate boronate ion in reactions with ethylene and propylene glycols. In: Inorganic Chemistry. 2008 ; Vol. 47, No. 5. pp. 1417-1419.
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    abstract = "The rate constants for a boronate ion were determined for the first time using the reaction systems of 3-nitrophenylboronic acid (3-NO 2PhB(OH)2) with ethylene glycol (EG) and propylene glycol (PG) in an alkaline solution: the rate constants (25°C, I = 0.10 M) for the reactions of 3-NO2PhB(OH)3 - are 1.2 M -1 s-1 (EG) and 1.5 M-1 s-1 (PG), which are at least 103 times smaller than those for the reactions of 3-NO2PhB(OH)2 [1.0 × 104 M-1 s-1 (EG) and 5.8 × 103 M-1 s-1 (PG)].",
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    AU - Miyamoto, Chiaki

    AU - Suzuki, Kazunori

    AU - Iwatsuki, Satoshi

    AU - Inamo, Masahiko

    AU - Takagi, Hideo D.

    AU - Ishihara, Koji

    PY - 2008/3/3

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    N2 - The rate constants for a boronate ion were determined for the first time using the reaction systems of 3-nitrophenylboronic acid (3-NO 2PhB(OH)2) with ethylene glycol (EG) and propylene glycol (PG) in an alkaline solution: the rate constants (25°C, I = 0.10 M) for the reactions of 3-NO2PhB(OH)3 - are 1.2 M -1 s-1 (EG) and 1.5 M-1 s-1 (PG), which are at least 103 times smaller than those for the reactions of 3-NO2PhB(OH)2 [1.0 × 104 M-1 s-1 (EG) and 5.8 × 103 M-1 s-1 (PG)].

    AB - The rate constants for a boronate ion were determined for the first time using the reaction systems of 3-nitrophenylboronic acid (3-NO 2PhB(OH)2) with ethylene glycol (EG) and propylene glycol (PG) in an alkaline solution: the rate constants (25°C, I = 0.10 M) for the reactions of 3-NO2PhB(OH)3 - are 1.2 M -1 s-1 (EG) and 1.5 M-1 s-1 (PG), which are at least 103 times smaller than those for the reactions of 3-NO2PhB(OH)2 [1.0 × 104 M-1 s-1 (EG) and 5.8 × 103 M-1 s-1 (PG)].

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