Direct kinetic measurements for the fast interconversion process between trigonal boronic acid and tetragonal boronate ion at low temperatures

Takeshi Matsumura; Satoshi Iwatsuki; Koji Ishihara

doi:10.1016/j.inoche.2005.05.011

Direct kinetic measurements for the fast interconversion process between trigonal boronic acid and tetragonal boronate ion at low temperatures

Takeshi Matsumura, Satoshi Iwatsuki, Koji Ishihara^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

14 Citations (Scopus)

Abstract

The rate constant, k₁, for the following addition reaction between 4-isopropyltropolonate (ipt^-) and meta-nitrophenylboronic acid (m-NO₂PhB(OH)₂) in acetonitrile was measured at various temperatures by using a low-temperature stopped-flow spectrophotometer:m-NO₂PhB(OH)₂+ipt ^-⇌k_-1k₁m-NO₂PhB(OH) ₂(ipt)^-;k₁ = 7.9 × 10⁴M ^-1 s^-1 at 25°C, ΔH₁*=34. 7±1.0kJmol^-1,ΔS₁*=-34.8±3. 8Jmol^-1K^-1, which indicates that the interconversion between the trigonal boronic acid and the tetrahedral boronate ion is much faster than the chelate formations for the complexation of boronic acid with bidentate ligands, but much slower than the diffusion-controlled reactions.

Original language	English
Pages (from-to)	713-716
Number of pages	4
Journal	Inorganic Chemistry Communication
Volume	8
Issue number	8
DOIs	https://doi.org/10.1016/j.inoche.2005.05.011
Publication status	Published - 2005 Aug

Keywords

4-Isopropyltropolonate
Interconversion
Kinetics
m-Nitrophenylboronic acid

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.inoche.2005.05.011

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@article{5ad778d3742c4ef3856a3a9276882070,

title = "Direct kinetic measurements for the fast interconversion process between trigonal boronic acid and tetragonal boronate ion at low temperatures",

abstract = "The rate constant, k1, for the following addition reaction between 4-isopropyltropolonate (ipt-) and meta-nitrophenylboronic acid (m-NO2PhB(OH)2) in acetonitrile was measured at various temperatures by using a low-temperature stopped-flow spectrophotometer:m-NO2PhB(OH)2+ipt -⇌k-1k1m-NO2PhB(OH) 2(ipt)-;k1 = 7.9 × 104M -1 s-1 at 25°C, ΔH1*=34. 7±1.0kJmol-1,ΔS1*=-34.8±3. 8Jmol-1K-1, which indicates that the interconversion between the trigonal boronic acid and the tetrahedral boronate ion is much faster than the chelate formations for the complexation of boronic acid with bidentate ligands, but much slower than the diffusion-controlled reactions.",

keywords = "4-Isopropyltropolonate, Interconversion, Kinetics, m-Nitrophenylboronic acid",

author = "Takeshi Matsumura and Satoshi Iwatsuki and Koji Ishihara",

note = "Funding Information: Financial Support from the 21COE program “Practical Nano-Chemistry” from MEXT, Japan, and Waseda University Grant for Special Research Projects are gratefully acknowledged. ",

year = "2005",

month = aug,

doi = "10.1016/j.inoche.2005.05.011",

language = "English",

volume = "8",

pages = "713--716",

journal = "Inorganic Chemistry Communication",

issn = "1387-7003",

publisher = "Elsevier BV",

number = "8",

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TY - JOUR

T1 - Direct kinetic measurements for the fast interconversion process between trigonal boronic acid and tetragonal boronate ion at low temperatures

AU - Matsumura, Takeshi

AU - Iwatsuki, Satoshi

AU - Ishihara, Koji

N1 - Funding Information: Financial Support from the 21COE program “Practical Nano-Chemistry” from MEXT, Japan, and Waseda University Grant for Special Research Projects are gratefully acknowledged.

PY - 2005/8

Y1 - 2005/8

N2 - The rate constant, k1, for the following addition reaction between 4-isopropyltropolonate (ipt-) and meta-nitrophenylboronic acid (m-NO2PhB(OH)2) in acetonitrile was measured at various temperatures by using a low-temperature stopped-flow spectrophotometer:m-NO2PhB(OH)2+ipt -⇌k-1k1m-NO2PhB(OH) 2(ipt)-;k1 = 7.9 × 104M -1 s-1 at 25°C, ΔH1*=34. 7±1.0kJmol-1,ΔS1*=-34.8±3. 8Jmol-1K-1, which indicates that the interconversion between the trigonal boronic acid and the tetrahedral boronate ion is much faster than the chelate formations for the complexation of boronic acid with bidentate ligands, but much slower than the diffusion-controlled reactions.

AB - The rate constant, k1, for the following addition reaction between 4-isopropyltropolonate (ipt-) and meta-nitrophenylboronic acid (m-NO2PhB(OH)2) in acetonitrile was measured at various temperatures by using a low-temperature stopped-flow spectrophotometer:m-NO2PhB(OH)2+ipt -⇌k-1k1m-NO2PhB(OH) 2(ipt)-;k1 = 7.9 × 104M -1 s-1 at 25°C, ΔH1*=34. 7±1.0kJmol-1,ΔS1*=-34.8±3. 8Jmol-1K-1, which indicates that the interconversion between the trigonal boronic acid and the tetrahedral boronate ion is much faster than the chelate formations for the complexation of boronic acid with bidentate ligands, but much slower than the diffusion-controlled reactions.

KW - 4-Isopropyltropolonate

KW - Interconversion

KW - Kinetics

KW - m-Nitrophenylboronic acid

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U2 - 10.1016/j.inoche.2005.05.011

DO - 10.1016/j.inoche.2005.05.011

M3 - Article

AN - SCOPUS:22044450522

SN - 1387-7003

VL - 8

SP - 713

EP - 716

JO - Inorganic Chemistry Communication

JF - Inorganic Chemistry Communication

IS - 8

ER -

Direct kinetic measurements for the fast interconversion process between trigonal boronic acid and tetragonal boronate ion at low temperatures

Abstract

Keywords

ASJC Scopus subject areas

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