Radical anions containing the dioxidated 1,2,5-thiadiazole heterocycle

被引：11

作者：

Virginia Mirifico, Maria ^{[1
,2
]}

Alberto Caram, Jose ^{[2
]}

Maria Gennaro, Ana ^{[3
,4
]}

Jorge Cobos, Carlos ^{[2
]}

Julio Vasini, Enrique ^{[2
]}

机构：

[1] Natl Univ La Plata, Fac Ingn, Area Dept Ingn Quim, RA-1900 La Plata, Argentina

[2] Natl Univ La Plata, Inst Invest Fisicoquim Teor & Aplicadas, Fac Ciencias Exactas, Dept Quim,INIFTA,CCT La Plata CONICET, RA-1900 La Plata, Argentina

[3] UNL, Fac Bioquim & Ciencias Biol, Santa Fe, Argentina

[4] INTEC, Inst Desarrollo Tecnol Ind Quim, RA-3000 Santa Fe, Argentina

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 2009年 / 22卷 / 10期

关键词：

radical anion; thiadiazoles; organic electrochemistry; ESR spectroscopy; DFT calculation; 3,4-DIPHENYL-1,2,5-THIADIAZOLE 1,1-DIOXIDE; NITROGENATED NUCLEOPHILES; CARRIER TRANSPORT; DERIVATIVES; THIADIAZOLE; ACETONITRILE; SIMULATION; EASYSPIN;

D O I：

10.1002/poc.1546

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Radical anions of 3,4-aryl disubstituted 1,2,5-thiadiazole 1,1-dioxide were obtained by chemical and electrochemical reduction of their substrates, and characterized by ESR spectroscopy and cyclic voltammetry. The radical anion of the phenanthro[9,10-c]-1,2,5-thiadiazole 1,1-dioxide was found to be very stable in an aprotic solvent solution and did not react readily when water was added to the aprotic solvent, or the solution was saturated with oxygen gas. The radical formation chemical reaction competed with nucleophilic addition to the C=N bond of the thiadiazoles. A possible reaction mechanism, and a common reaction intermediate, supported by density functional theory calculations, is presented for the most stable radical. Copyright (C) 2009 John Wiley & Sons, Ltd.

引用

页码：964 / 970

页数：7

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