Electrochemical behavior of a Cypridina luciferin analogue in acetonitrile solutions in the presence of proton acceptors

被引:5
作者
Okajima, T [1 ]
Tokuda, K [1 ]
Ohsaka, T [1 ]
机构
[1] Tokyo Inst Technol, Interdisciplinary Grad Sch Sci & Engn, Dept Elect Chem, Midori Ku, Yokohama, Kanagawa 2268502, Japan
关键词
Cypridina luciferin analogues; redox reactions; dimerization; hydroxylation; cyclic voltammetry; double potential-step chronoamperometry; hydrodynamic voltammetry;
D O I
10.1016/S0022-0728(99)00362-9
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
The electrochemical redox behavior of the Cypridina luciferin analogue, 6-(4-methoxyphenyl)-2-methylimidazo[1, 2-a]pyrazin-3(7H)-one (MCLA) has been examined in acetonitrile solutions containing 2,6-lutidine or water using cyclic and hydrodynamic voltammetry and double potential-step chronoamperometry. The conjugate base of MCLA (MCLA(-)) is oxidized in two one-electron steps to the radical species (MCLA(.)) and further to the carbocation species (MCLA(+)). The radical-radical coupling of MCLA(.) yields the corresponding dimer ((MCLA)(2)), which is in equilibrium with MCLA(.). MCLA(+) undergoes the addition of a water molecule to yield a hydroxylated form (MCLA-OH) of luciferinol type. The whole mechanism of the electrochemical redox reactions of MCLA(-) coupled with these chemical reactions has been found to be essentially the same as that proposed for the chemical redox reactions of Cypridina luciferin and its analogues, and in addition the kinetic data. concerning the dimerization of MCLA(.), the dissociation of (MCLA)(2) and the hydroxylation of MCLA(+) have been estimated together with the diffusion coefficient of MCLA(-). (C) 1999 Elsevier Science S.A. All rights reserved.
引用
收藏
页码:46 / 53
页数:8
相关论文
共 24 条
[1]   CHEMILUMINESCENCE OF CIPRIDINA LUCIFERIN ANALOGS .2. KINETIC-STUDIES ON THE REACTION OF 2-METHYL-6-PHENYLIMIDAZO[1,2-A]PYRAZIN-3(7H)-ONE (CLA) WITH SUPEROXIDE - HYDROPEROXYL RADICAL IS AN ACTUAL ACTIVE SPECIES USED TO INITIATE THE REACTION [J].
AKUTSU, K ;
NAKAJIMA, H ;
KATOH, T ;
KINO, S ;
FUJIMORI, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1995, (08) :1699-1706
[2]   ARE ANION RADICALS UNABLE TO UNDERGO RADICAL RADICAL DIMERIZATION [J].
AMATORE, C ;
PINSON, J ;
SAVEANT, JM .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1982, 137 (01) :143-148
[3]   KINETIC-ANALYSIS OF REVERSIBLE ELECTRODIMERIZATION REACTIONS BY THE COMBINED USE OF DOUBLE POTENTIAL STEP CHRONOAMPEROMETRY AND LINEAR SWEEP VOLTAMMETRY - APPLICATION TO THE REDUCTION OF 9-CYANOANTHRACENE [J].
AMATORE, C ;
GARREAU, D ;
HAMMI, M ;
PINSON, J ;
SAVEANT, JM .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1985, 184 (01) :1-24
[4]   ELECTRODIMERIZATION .1. ONE-ELECTRON IRREVERSIBLE DIMERIZATION - DIAGNOSTIC CRITERIA AND RATE DETERMINATION PROCEDURES FOR VOLTAMMETRIC STUDIES [J].
ANDRIEUX, CP ;
NADJO, L ;
SAVEANT, JM .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1970, 26 (01) :147-&
[5]  
Bard A. J., 1980, ELECTROCHEMICAL METH
[6]   ELECTROCHEMISTRY OF THE VIOLOGENS [J].
BIRD, CL ;
KUHN, AT .
CHEMICAL SOCIETY REVIEWS, 1981, 10 (01) :49-82
[7]   REVERSIBLE DIMERIZATION OF PHENOXYL RADICALS FORMED BY ANODIC-OXIDATION OF PHENOLATES - A QUANTITATIVE STUDY BY CYCLIC VOLTAMMETRY [J].
EVANS, DH ;
JIMENEZ, PJ ;
KELLY, MJ .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1984, 163 (1-2) :145-157
[8]   CHEMILUMINESCENCE OF CYPRIDINA LUCIFERIN ANALOGS .1. EFFECT OF PH ON RATES OF SPONTANEOUS AUTOXIDATION OF CLA IN AQUEOUS BUFFER SOLUTIONS [J].
FUJIMORI, K ;
NAKAJIMA, H ;
AKUTSU, K ;
MITANI, M ;
SAWADA, H ;
NAKAYAMA, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (12) :2405-2409
[9]  
GOTO T, 1968, Pure and Applied Chemistry, V17, P421, DOI 10.1351/pac196817030421
[10]  
GOTO T, 1988, STUDIES ORGANIC CHEM, P367