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

被引：36

作者：

Miyamoto, Chiaki ^{[1
]}

Suzuki, Kazunori ^{[1
]}

Iwatsuki, Satoshi ^{[2
]}

Inamo, Masahiko ^{[3
]}

Takagi, Hideo D. ^{[4
]}

Ishihara, Koji ^{[1
,5
]}

机构：

[1] Waseda Univ, Sch Adv Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, Japan

[2] Konan Univ, Dept Chem Funct Mol, Kobe, Hyogo 6588501, Japan

[3] Aichi Univ Educ, Dept Chem, Kariya, Aichi 4488542, Japan

[4] Nagoya Univ, Ctr Mat Res Sci, Inorgan Chem Div, Nagoya, Aichi 4648602, Japan

[5] Waseda Univ, Grad Sch Sci & Engn, Mat Res Lab Biosci & Photon, Shinjuku Ku, Tokyo 1698555, Japan

来源：

INORGANIC CHEMISTRY | 2008年 / 47卷 / 05期

关键词：

D O I：

10.1021/ic702317n

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

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 103 times smaller than those for the reactions of 3-NO2PhB(OH)(2) [1.0 X 10(4) M-1 S-1 (EG) and 5.8 x 10(3) M-1 S-1 (PG)].

引用

页码：1417 / 1419

页数：3

共 29 条

[1] DYNAMICS OF BORON ACID COMPLEXATION REACTIONS - FORMATION OF 1-1 BORON ACID LIGAND COMPLEXES [J].

BABCOCK, L ;

PIZER, R .

INORGANIC CHEMISTRY, 1980, 19 (01) :56-61

[2] Boronic acid fluorescent sensors for monosaccharide signaling based on the 6-methoxyquinolinium heterocyclic nucleus: progress toward noninvasive and continuous glucose monitoring [J].

Badugu, R ;

Lakowicz, JR ;

Geddes, CD .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (01) :113-119

[3] COMPLEXATION OF PHENYLBORONIC ACID WITH LACTIC-ACID - STABILITY CONSTANT AND REACTION-KINETICS [J].

FRIEDMAN, S ;

PACE, B ;

PIZER, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (17) :5381-5384

[4] MECHANISM OF COMPLEXATION OF PHENYLBORONIC ACID WITH OXALIC-ACID - REACTION WHICH REQUIRES LIGAND DONOR ATOM PROTONATION [J].

FRIEDMAN, S ;

PIZER, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (21) :6059-6062

[5]

Hall D, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, pXV

[6] KINETIC-STUDY OF BORIC ACID-BORATE INTERCHANGE IN AQUEOUS-SOLUTION BY B-11 NMR-SPECTROSCOPY [J].

ISHIHARA, K ;

NAGASAWA, A ;

UMEMOTO, K ;

ITO, H ;

SAITO, K .

INORGANIC CHEMISTRY, 1994, 33 (17) :3811-3816

[7] MECHANISTIC STUDY OF THE COMPLEX-FORMATION OF BORIC-ACID [J].

ISHIHARA, K ;

MOURI, Y ;

FUNAHASHI, S ;

TANAKA, M .

INORGANIC CHEMISTRY, 1991, 30 (10) :2356-2360

[8] Kinetic study of the complex formation of boric and boronic acids with mono- and diprotonated ligands [J].

Ito, H ;

Kono, Y ;

Machida, A ;

Mitsumoto, Y ;

Omori, K ;

Nakamura, N ;

Kondo, Y ;

Ishihara, K .

INORGANICA CHIMICA ACTA, 2003, 344 :28-36

[9] Which is reactive in alkaline solution, boronate ion or boronic acid? Kinetic evidence for reactive trigonal boronic acid in an alkaline solution [J].

Iwatsuki, Satoshi ;

Nakajima, Shihoko ;

Inamo, Masahiko ;

Takagi, Hideo D. ;

Ishihara, Koji .

INORGANIC CHEMISTRY, 2007, 46 (02) :354-356

[10]

JORDAN RB, 1998, REACTION MECH INORGA, P88

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