Mechanistic study on the reaction of boronic acids with H-resorcinol

Norihiro Takao; Akiko Suto; Yuichi Kondo; Koji Ishihara

doi:10.1016/S0020-1693(99)00152-8

Mechanistic study on the reaction of boronic acids with H-resorcinol

Norihiro Takao, Akiko Suto, Yuichi Kondo, Koji Ishihara^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

12 Citations (Scopus)

Abstract

Kinetics for the reaction of m-nitrophenyl- (m-NO₂Ph-), phenyl- (Ph-), methyl(Me-), and n-butyl- (n-Bu-) boronic acids with H-resorcinol has been studied at various temperatures and pressures. The pseudo first-order rate constant (k_obs) exhibited saturation in the plot of k_obs against the total boronic acid concentration (C_B) for the reactions of m-NO₂PhB(OH)₂ and PhB(OH)₂, while the plot was linear for the reactions of MeB(OH)₂ and n-BuB(OH)₂, which leads to the following equations, respectively: k_obs=k*KC_B/(1+KC_B) and k_obs=k*KC_B=k_fC_B. It was experimentally shown that the reaction of boronic acids with H-resorcinol proceeds with rate determining second chelate-ring closure.

Original language	English
Pages (from-to)	222-227
Number of pages	6
Journal	Inorganica Chimica Acta
Volume	290
Issue number	2
DOIs	https://doi.org/10.1016/S0020-1693(99)00152-8
Publication status	Published - 1999 Jul 15

Keywords

Boronic acid
H-resorcinol
Kinetics and mechanism

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/S0020-1693(99)00152-8

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title = "Mechanistic study on the reaction of boronic acids with H-resorcinol",

abstract = "Kinetics for the reaction of m-nitrophenyl- (m-NO2Ph-), phenyl- (Ph-), methyl(Me-), and n-butyl- (n-Bu-) boronic acids with H-resorcinol has been studied at various temperatures and pressures. The pseudo first-order rate constant (kobs) exhibited saturation in the plot of kobs against the total boronic acid concentration (CB) for the reactions of m-NO2PhB(OH)2 and PhB(OH)2, while the plot was linear for the reactions of MeB(OH)2 and n-BuB(OH)2, which leads to the following equations, respectively: kobs=k*KCB/(1+KCB) and kobs=k*KCB=kfCB. It was experimentally shown that the reaction of boronic acids with H-resorcinol proceeds with rate determining second chelate-ring closure.",

keywords = "Boronic acid, H-resorcinol, Kinetics and mechanism",

author = "Norihiro Takao and Akiko Suto and Yuichi Kondo and Koji Ishihara",

year = "1999",

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doi = "10.1016/S0020-1693(99)00152-8",

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TY - JOUR

T1 - Mechanistic study on the reaction of boronic acids with H-resorcinol

AU - Takao, Norihiro

AU - Suto, Akiko

AU - Kondo, Yuichi

AU - Ishihara, Koji

PY - 1999/7/15

Y1 - 1999/7/15

N2 - Kinetics for the reaction of m-nitrophenyl- (m-NO2Ph-), phenyl- (Ph-), methyl(Me-), and n-butyl- (n-Bu-) boronic acids with H-resorcinol has been studied at various temperatures and pressures. The pseudo first-order rate constant (kobs) exhibited saturation in the plot of kobs against the total boronic acid concentration (CB) for the reactions of m-NO2PhB(OH)2 and PhB(OH)2, while the plot was linear for the reactions of MeB(OH)2 and n-BuB(OH)2, which leads to the following equations, respectively: kobs=k*KCB/(1+KCB) and kobs=k*KCB=kfCB. It was experimentally shown that the reaction of boronic acids with H-resorcinol proceeds with rate determining second chelate-ring closure.

AB - Kinetics for the reaction of m-nitrophenyl- (m-NO2Ph-), phenyl- (Ph-), methyl(Me-), and n-butyl- (n-Bu-) boronic acids with H-resorcinol has been studied at various temperatures and pressures. The pseudo first-order rate constant (kobs) exhibited saturation in the plot of kobs against the total boronic acid concentration (CB) for the reactions of m-NO2PhB(OH)2 and PhB(OH)2, while the plot was linear for the reactions of MeB(OH)2 and n-BuB(OH)2, which leads to the following equations, respectively: kobs=k*KCB/(1+KCB) and kobs=k*KCB=kfCB. It was experimentally shown that the reaction of boronic acids with H-resorcinol proceeds with rate determining second chelate-ring closure.

KW - Boronic acid

KW - H-resorcinol

KW - Kinetics and mechanism

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U2 - 10.1016/S0020-1693(99)00152-8

DO - 10.1016/S0020-1693(99)00152-8

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AN - SCOPUS:0012818932

SN - 0020-1693

VL - 290

SP - 222

EP - 227

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

IS - 2

ER -

Mechanistic study on the reaction of boronic acids with H-resorcinol

Abstract

Keywords

ASJC Scopus subject areas

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