Inorganic Chemistry 2008-03-03

Kinetic evidence for high reactivity of 3-nitrophenylboronic acid compared to its conjugate boronate ion in reactions with ethylene and propylene glycols.

Chiaki Miyamoto, Kazunori Suzuki, Satoshi Iwatsuki, Masahiko Inamo, Hideo D Takagi, Koji Ishihara

Index: Inorg. Chem. 47(5) , 1417-9, (2008)

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Abstract

The rate constants for a boronate ion were determined for the first time using the reaction systems of 3-nitrophenylboronic acid (3-NO2PhB(OH)2) with ethylene glycol (EG) and propylene glycol (PG) in an alkaline solution: the rate constants (25 degrees C, I = 0.10 M) for the reactions of 3-NO2PhB(OH)3- are 1.2 M(-1) s(-1) (EG) and 1.5 M(-1) s(-1) (PG), which are at least 10(3) times smaller than those for the reactions of 3-NO 2PhB(OH)2 [1.0 x 10(4) M(-1) s(-1) (EG) and 5.8 x 10(3) M(-1) s(-1) (PG)].