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

doi:10.1021/ic702317n

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^*

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

32 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 language	English
Pages (from-to)	1417-1419
Number of pages	3
Journal	Inorganic Chemistry
Volume	47
Issue number	5
DOIs	https://doi.org/10.1021/ic702317n
Publication status	Published - 2008 Mar 3

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry

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

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)].",

author = "Chiaki Miyamoto and Kazunori Suzuki and Satoshi Iwatsuki and Masahiko Inamo and Takagi, {Hideo D.} and Koji Ishihara",

year = "2008",

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doi = "10.1021/ic702317n",

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volume = "47",

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journal = "Inorganic Chemistry",

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publisher = "American Chemical Society",

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T1 - Kinetic evidence for high reactivity of 3-nitrophenylboronic acid compared to its conjugate boronate ion in reactions with ethylene and propylene glycols

AU - Miyamoto, Chiaki

AU - Suzuki, Kazunori

AU - Iwatsuki, Satoshi

AU - Inamo, Masahiko

AU - Takagi, Hideo D.

AU - Ishihara, Koji

PY - 2008/3/3

Y1 - 2008/3/3

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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JO - Inorganic Chemistry

JF - Inorganic Chemistry

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

Abstract

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