Relative kinetic reactivity of boronic acid and boronate ion towards Tiron, 2,2′-biphenol, and propylene glycol

Eisuke Watanabe; Chiaki Miyamoto; Asumi Tanaka; Kenzo Iizuka; Satoshi Iwatsuki; Masahiko Inamo; Hideo D. Takagi; Koji Ishihara

doi:10.1039/c3dt50283j

Relative kinetic reactivity of boronic acid and boronate ion towards Tiron, 2,2′-biphenol, and propylene glycol

Eisuke Watanabe, Chiaki Miyamoto, Asumi Tanaka, Kenzo Iizuka, Satoshi Iwatsuki, Masahiko Inamo, Hideo D. Takagi, Koji Ishihara^*

^*この研究の対応する著者

先進理工学部

研究成果: Article › 査読

23 被引用数 (Scopus)

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Reaction systems of boronic acid (RB(OH₂), R = phenyl or 3-fluorophenyl) with diols and no proton ambiguity were elaborately set up, and kinetic measurements were conducted to elucidate the relative reactivities of RB(OH)₂ and RB(OH)₃^-. In the reactions of phenylboronic and 3-fluorophenylboronic acids with propylene glycol, the reactivity order was: RB(OH)₂ >> RB(OH)₃ ^-, whereas in the reactions of 3-pyridylboronic acid with Tiron and 2,2′-biphenol, the reactivity of RB(OH)₂ was comparable to that of RB(OH)₃^-. These results are in contrast to those that have been previously reported, and widely accepted for over thirty years, that concluded that the reactivity of RB(OH)₃^- is several orders of magnitude higher than that of RB(OH)₂. The reactivity of Tiron with 3-pyridylboronic acid is affected by the protonation of one of its sulfonate groups.

本文言語	English
ページ（範囲）	8446-8453
ページ数	8
ジャーナル	Dalton Transactions
巻	42
号	23
DOI	https://doi.org/10.1039/c3dt50283j
出版ステータス	Published - 2013 6月 21

ASJC Scopus subject areas

無機化学

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title = "Relative kinetic reactivity of boronic acid and boronate ion towards Tiron, 2,2′-biphenol, and propylene glycol",

abstract = "Reaction systems of boronic acid (RB(OH2), R = phenyl or 3-fluorophenyl) with diols and no proton ambiguity were elaborately set up, and kinetic measurements were conducted to elucidate the relative reactivities of RB(OH)2 and RB(OH)3-. In the reactions of phenylboronic and 3-fluorophenylboronic acids with propylene glycol, the reactivity order was: RB(OH)2 >> RB(OH)3 -, whereas in the reactions of 3-pyridylboronic acid with Tiron and 2,2′-biphenol, the reactivity of RB(OH)2 was comparable to that of RB(OH)3-. These results are in contrast to those that have been previously reported, and widely accepted for over thirty years, that concluded that the reactivity of RB(OH)3- is several orders of magnitude higher than that of RB(OH)2. The reactivity of Tiron with 3-pyridylboronic acid is affected by the protonation of one of its sulfonate groups.",

author = "Eisuke Watanabe and Chiaki Miyamoto and Asumi Tanaka and Kenzo Iizuka and Satoshi Iwatsuki and Masahiko Inamo and Takagi, {Hideo D.} and Koji Ishihara",

year = "2013",

month = jun,

day = "21",

doi = "10.1039/c3dt50283j",

language = "English",

volume = "42",

pages = "8446--8453",

journal = "Dalton Transactions",

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publisher = "Royal Society of Chemistry",

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T1 - Relative kinetic reactivity of boronic acid and boronate ion towards Tiron, 2,2′-biphenol, and propylene glycol

AU - Watanabe, Eisuke

AU - Miyamoto, Chiaki

AU - Tanaka, Asumi

AU - Iizuka, Kenzo

AU - Iwatsuki, Satoshi

AU - Inamo, Masahiko

AU - Takagi, Hideo D.

AU - Ishihara, Koji

PY - 2013/6/21

Y1 - 2013/6/21

N2 - Reaction systems of boronic acid (RB(OH2), R = phenyl or 3-fluorophenyl) with diols and no proton ambiguity were elaborately set up, and kinetic measurements were conducted to elucidate the relative reactivities of RB(OH)2 and RB(OH)3-. In the reactions of phenylboronic and 3-fluorophenylboronic acids with propylene glycol, the reactivity order was: RB(OH)2 >> RB(OH)3 -, whereas in the reactions of 3-pyridylboronic acid with Tiron and 2,2′-biphenol, the reactivity of RB(OH)2 was comparable to that of RB(OH)3-. These results are in contrast to those that have been previously reported, and widely accepted for over thirty years, that concluded that the reactivity of RB(OH)3- is several orders of magnitude higher than that of RB(OH)2. The reactivity of Tiron with 3-pyridylboronic acid is affected by the protonation of one of its sulfonate groups.

AB - Reaction systems of boronic acid (RB(OH2), R = phenyl or 3-fluorophenyl) with diols and no proton ambiguity were elaborately set up, and kinetic measurements were conducted to elucidate the relative reactivities of RB(OH)2 and RB(OH)3-. In the reactions of phenylboronic and 3-fluorophenylboronic acids with propylene glycol, the reactivity order was: RB(OH)2 >> RB(OH)3 -, whereas in the reactions of 3-pyridylboronic acid with Tiron and 2,2′-biphenol, the reactivity of RB(OH)2 was comparable to that of RB(OH)3-. These results are in contrast to those that have been previously reported, and widely accepted for over thirty years, that concluded that the reactivity of RB(OH)3- is several orders of magnitude higher than that of RB(OH)2. The reactivity of Tiron with 3-pyridylboronic acid is affected by the protonation of one of its sulfonate groups.

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DO - 10.1039/c3dt50283j

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AN - SCOPUS:84878030792

SN - 1477-9226

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EP - 8453

JO - Dalton Transactions

JF - Dalton Transactions

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Relative kinetic reactivity of boronic acid and boronate ion towards Tiron, 2,2′-biphenol, and propylene glycol

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