Which is reactive in alkaline solution, boronate ion or boronic acid? Kinetic evidence for reactive trigonal boronic acid in an alkaline solution

被引:56
作者
Iwatsuki, Satoshi
Nakajima, Shihoko
Inamo, Masahiko
Takagi, Hideo D.
Ishihara, Koji
机构
[1] Waseda Univ, Sch Sci & Engn, Dept Chem, Shinjuku Ku, Tokyo 1698555, Japan
[2] Waseda Univ, Adv Res Inst Sci & Engn, Shinjuku Ku, Tokyo 1698555, Japan
[3] Aichi Univ Educ, Dept Chem, Kariya, Aichi 4488542, Japan
[4] Nagoya Univ, Res Ctr Mat Sci, Inorgan Chem Div, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[5] Waseda Univ, Grad Sch Sci & Engn, Mat Res Lab Biosci & Photon, Shinjuku Ku, Tokyo 1698555, Japan
关键词
D O I
10.1021/ic0615372
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
That boronic acid is a reactive species toward a diol moiety even in an alkaline solution and that the boronate ion is not very reactive were demonstrated by the estimated upper limit of the rate constants for the reactions of some boronic acids with 2,2'-biphenol and 2,3-dihydroxynaphthalene in a neutral-alkaline solution, which will correct a common misunderstanding in boron chemistry and would renew the idea of effective boronic acid sensor design for carbohydrates.
引用
收藏
页码:354 / 356
页数:3
相关论文
共 26 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]   Determination of the mode and efficacy of the cross-linking of guar by borate using MAS 11B NMR of borate cross-linked guar in combination with solution 11B NMR of model systems [J].
Bishop, M ;
Shahid, N ;
Yang, JZ ;
Barron, AR .
DALTON TRANSACTIONS, 2004, (17) :2621-2634
[4]   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
[5]   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
[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]   Redox and acidity properties of 2,2′- and 4,4′-biphenol and the corresponding phenoxyl radicals [J].
Jonsson, M ;
Lind, J ;
Merényi, G .
JOURNAL OF PHYSICAL CHEMISTRY A, 2002, 106 (18) :4758-4762
[10]  
JORDAN RB, 1998, REACTION MECH INORGA, P88