Substituent effect on the redox potential of substituted (aryl)(2-nitrobenzo[b]thiophen-3-yl)amines

被引:12
作者
Cosimelli, B
Spinelli, D
Costanzo, F
Tonelli, D
Lamartina, L
Sarvà, MC
Seeber, R
机构
[1] Dipartimento Chim Organ A Mangini, I-40127 Bologna, Italy
[2] Dipartimento Chim Fis & Inorgan, I-40136 Bologna, Italy
[3] Dipartimento Chim & Tecnol Farmaceut, I-90123 Palermo, Italy
[4] Ist Chim Farmaceut & Tossicol, I-95125 Catania, Italy
[5] Dipartimento Chim, I-41100 Modena, Italy
关键词
(aryl)(2-nitrobenzo[b]thiophen-3-yl)amines; reduction potential; structure-reactivity; linear free energy relations;
D O I
10.1016/S0040-4020(00)01166-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The electronic effect of some meta- or para-substituents on the reduction of the title compounds has been investigated. The reversible reduction potential values of these compounds have been evaluated by cyclic voltammetry at a mercury electrode in 0.1 M tetraethylammoniumtetrafluoroborate, dimethylsulfoxide solutions. The substituent effect depends on both its nature and its position. The reduction potential Values of the derivatives studied have been correlated with the Hammett substituent constants. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1857 / 1860
页数:4
相关论文
共 31 条
[1]  
BARD AJ, 1980, ELECTROCHEMICAL METH, pCH6
[2]  
BONTEMPELLI G, 1989, ANN CHIM-ROME, V79, P103
[3]   2-(SUBSTITUTED PHENYL)OXAZOLO[4,5-B]PYRIDINES AND 2-(SUBSTITUTED PHENYL)OXAZOLO[5,4-B]PYRIDINES AS NON-ACIDIC ANTI-INFLAMMATORY AGENTS [J].
CLARK, RL ;
PESSOLANO, AA ;
WITZEL, B ;
LANZA, T ;
SHEN, TY ;
VANARMAN, CG ;
RISLEY, EA .
JOURNAL OF MEDICINAL CHEMISTRY, 1978, 21 (11) :1158-1162
[4]  
Exner O., 1988, Correlation Analysis of Chemical Data
[5]  
FOURNARI P, 1963, B SOC CHIM FR, P484
[6]  
FOURNARI P, 1963, B SOC CHIM FR, P488
[7]  
GUERRERA F, 1990, FARMACO, V45, P29
[8]   ON THE REACTION BETWEEN 3-BROMO-2-NITROBENZO[B]THIOPHENE AND SOME AMINES - A NOVEL AROMATIC NUCLEOPHILIC-SUBSTITUTION WITH REARRANGEMENT [J].
GUERRERA, F ;
SALERNO, L ;
LAMARTINA, L ;
SPINELLI, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (10) :1243-1246
[9]  
GUERRERA F, 1992, FARMACO, V47, P1149
[10]   ANALYSIS OF METABOLISM AND GENOTOXICITY OF 5-NITRO-3-THIOPHENECARBOXANILIDES IN BACTERIAL, MAMMALIAN AND HUMAN-CELLS [J].
HRELIA, P ;
VIGAGNI, F ;
MAFFEI, F ;
FIMOGNARI, C ;
LAMARTINA, L ;
SPINELLI, D ;
JURIC, P ;
GUERRA, MC ;
CANTELLIFORTI, G .
MUTAGENESIS, 1995, 10 (03) :171-177