Detailed Reaction Mechanism of Phenylboronic Acid with Alizarin Red S in Aqueous Solution: Re-Investigation with Spectrophotometry and Fluorometry

Yota Suzuki; Tomoaki Sugaya; Satoshi Iwatsuki; Masahiko Inamo; Hideo D. Takagi; Akira Odani; Koji Ishihara

doi:10.1002/slct.201700166

Detailed Reaction Mechanism of Phenylboronic Acid with Alizarin Red S in Aqueous Solution: Re-Investigation with Spectrophotometry and Fluorometry

Yota Suzuki, Tomoaki Sugaya, Satoshi Iwatsuki, Masahiko Inamo, Hideo D. Takagi, Akira Odani, Koji Ishihara

School of Advanced Science and Engineering

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

6 Citations (Scopus)

Abstract

Re-investigation of the reaction of phenylboronic acid (PhB(OH)₂) with Alizarin Red S (ARS, H₂L) was carried out using absorption and emission spectrophotometry to correct the currently proposed mechanism. Kinetic results obtained by both methods, which essentially show no significant differences, showed that the kinetic reactivity of ARS toward PhB(OH)₂ was in the order H₂L < HL^– and that of phenylboronic acid toward HL^– was PhB(OH)₂ > PhB(OH)₃ ^–. Acetic acid/acetate buffer accelerated the present reaction, though HEPES buffer did not. A detailed reaction mechanism involving the acceleration effect of the acetate buffer is proposed for the present reaction on the basis of a recent universal reaction mechanism.

Original language	English
Pages (from-to)	2956-2964
Number of pages	9
Journal	ChemistrySelect
Volume	2
Issue number	10
DOIs	https://doi.org/10.1002/slct.201700166
Publication status	Published - 2017 Apr 3

Keywords

Alizarin Red S
Kinetics
Phenylboronic acid
Reaction mechanism

ASJC Scopus subject areas

Chemistry(all)

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10.1002/slct.201700166

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Detailed Reaction Mechanism of Phenylboronic Acid with Alizarin Red S in Aqueous Solution : Re-Investigation with Spectrophotometry and Fluorometry. / Suzuki, Yota; Sugaya, Tomoaki; Iwatsuki, Satoshi; Inamo, Masahiko; Takagi, Hideo D.; Odani, Akira; Ishihara, Koji.

In: ChemistrySelect, Vol. 2, No. 10, 03.04.2017, p. 2956-2964.

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

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title = "Detailed Reaction Mechanism of Phenylboronic Acid with Alizarin Red S in Aqueous Solution: Re-Investigation with Spectrophotometry and Fluorometry",

abstract = "Re-investigation of the reaction of phenylboronic acid (PhB(OH)2) with Alizarin Red S (ARS, H2L) was carried out using absorption and emission spectrophotometry to correct the currently proposed mechanism. Kinetic results obtained by both methods, which essentially show no significant differences, showed that the kinetic reactivity of ARS toward PhB(OH)2 was in the order H2L < HL– and that of phenylboronic acid toward HL– was PhB(OH)2 > PhB(OH)3 –. Acetic acid/acetate buffer accelerated the present reaction, though HEPES buffer did not. A detailed reaction mechanism involving the acceleration effect of the acetate buffer is proposed for the present reaction on the basis of a recent universal reaction mechanism.",

keywords = "Alizarin Red S, Kinetics, Phenylboronic acid, Reaction mechanism",

author = "Yota Suzuki and Tomoaki Sugaya and Satoshi Iwatsuki and Masahiko Inamo and Takagi, {Hideo D.} and Akira Odani and Koji Ishihara",

note = "Funding Information: We wish to thank JSPS KAKENHI Grant Number 25410150 and Waseda University Grants for Special Research Projects (2014 K-6156 and 2016B-177) for financial support. We would like to thank Editage (www.editage.jp) for English language editing. Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2017",

month = apr,

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doi = "10.1002/slct.201700166",

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AU - Iwatsuki, Satoshi

AU - Inamo, Masahiko

AU - Takagi, Hideo D.

AU - Odani, Akira

AU - Ishihara, Koji

N1 - Funding Information: We wish to thank JSPS KAKENHI Grant Number 25410150 and Waseda University Grants for Special Research Projects (2014 K-6156 and 2016B-177) for financial support. We would like to thank Editage (www.editage.jp) for English language editing. Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2017/4/3

Y1 - 2017/4/3

N2 - Re-investigation of the reaction of phenylboronic acid (PhB(OH)2) with Alizarin Red S (ARS, H2L) was carried out using absorption and emission spectrophotometry to correct the currently proposed mechanism. Kinetic results obtained by both methods, which essentially show no significant differences, showed that the kinetic reactivity of ARS toward PhB(OH)2 was in the order H2L < HL– and that of phenylboronic acid toward HL– was PhB(OH)2 > PhB(OH)3 –. Acetic acid/acetate buffer accelerated the present reaction, though HEPES buffer did not. A detailed reaction mechanism involving the acceleration effect of the acetate buffer is proposed for the present reaction on the basis of a recent universal reaction mechanism.

AB - Re-investigation of the reaction of phenylboronic acid (PhB(OH)2) with Alizarin Red S (ARS, H2L) was carried out using absorption and emission spectrophotometry to correct the currently proposed mechanism. Kinetic results obtained by both methods, which essentially show no significant differences, showed that the kinetic reactivity of ARS toward PhB(OH)2 was in the order H2L < HL– and that of phenylboronic acid toward HL– was PhB(OH)2 > PhB(OH)3 –. Acetic acid/acetate buffer accelerated the present reaction, though HEPES buffer did not. A detailed reaction mechanism involving the acceleration effect of the acetate buffer is proposed for the present reaction on the basis of a recent universal reaction mechanism.

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Detailed Reaction Mechanism of Phenylboronic Acid with Alizarin Red S in Aqueous Solution: Re-Investigation with Spectrophotometry and Fluorometry

Abstract

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