Kinetic evidence for high reactivity of 3-nitrophenylboronic acid compared to its conjugate boronate ion in reactions with ethylene and propylene glycols.
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)].
Miyamoto
Chiaki
C
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan.
Suzuki
Kazunori
K
Iwatsuki
Satoshi
S
Inamo
Masahiko
M
Takagi
Hideo D
HD
Ishihara
Koji
K
D001897:Boronic Acids / Q000737:chemistry*; D019855:Ethylene Glycol / Q000737:chemistry*; D007700:Kinetics; D019946:Propylene Glycol / Q000737:chemistry*
D001897:Boronic Acids; C017562:3-nitrobenzeneboronic acid; D019946:Propylene Glycol; D019855:Ethylene Glycol