Mechanistic study on the reaction of boronic acids with H-resorcinol |
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Authors: | Norihiro Takao Akiko Suto Yuichi Kondo Koji Ishihara |
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Institution: | Department of Chemistry, School of Science and Engineering, Waseda University, Okubo, Shinjuku-ku, Tokyo 169-8555, Japan |
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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. |
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Keywords: | Kinetics and mechanism Boronic acid H-resorcinol |
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