Synthesis of a new stable and water-soluble tris(4-hydroxysulfonyl-tetrachlorophenyl)methyl radical with selective oxidative capacity

被引:11
作者
Antonio Mesa, Juan [1 ]
Velazquez-Palenzuela, Amado [2 ]
Brillas, Enric [2 ]
Lluis Torres, Josep [1 ]
Julia, Luis [1 ]
机构
[1] CSIC, Inst Quim Avancada Catalunya, Dept Quim Biol & Modelitzacio Mol, ES-08034 Barcelona, Spain
[2] Univ Barcelona, Dept Quim Fis, E-08028 Barcelona, Spain
关键词
Free radical; Radical-scavenging; Chemosensor; Electron paramagnetic resonance; ELECTRON-TRANSFER CAPACITY; CARBON FREE-RADICALS; ANTIOXIDANT ACTIVITY; POLYPHENOLS; SERIES; CELLS; DERIVATIVES; FRACTIONS; POWER; BARK;
D O I
10.1016/j.tet.2011.02.069
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学];
摘要
A new stable organic free radical of the PTM (perchlorotriphenylmethyl) series very soluble in water is reported. This free radical is sensitive to electron transfer processes, and the selectivity of these reactions in the presence of ascorbic acid, pyrogallol, and catechol as reducing species is described. The electron paramagnetic resonance spectrum and the electrochemical behavior are also presented. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3119 / 3123
页数:5
相关论文
共 19 条
[1]
INERT CARBON FREE-RADICALS .8. POLYCHLOROTRIPHENYLMETHYL RADICALS - SYNTHESIS, STRUCTURE, AND SPIN-DENSITY DISTRIBUTION [J].
ARMET, O ;
VECIANA, J ;
ROVIRA, C ;
RIERA, J ;
CASTANER, J ;
MOLINS, E ;
RIUS, J ;
MIRAVITLLES, C ;
OLIVELLA, S ;
BRICHFEUS, J .
JOURNAL OF PHYSICAL CHEMISTRY, 1987, 91 (22) :5608-5616
[2]
BALLESTER M, 1986, SYNTHESIS-STUTTGART, P64
[3]
INERT CARBON FREE RADICALS .1. PERCHLORODIPHENYLMETHYL AND PERCHLOROTRIPHENYLMETHYL RADICAL SERIES [J].
BALLESTER, M ;
RIERA, J ;
CASTANER, J ;
BADIA, C ;
MONSO, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (09) :2215-+
[4]
INERT FREE-RADICALS (IFR) - A UNIQUE TRIVALENT CARBON SPECIES [J].
BALLESTER, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (12) :380-387
[5]
2 FUNCTIONALIZED FREE-RADICALS OF THE TRIS(2,4,6-TRICHLOROPHENYL)METHYL RADICAL SERIES - SYNTHESIS, STABILITY AND EPR ANALYSIS [J].
CARILLA, J ;
FAJARI, L ;
JULIA, L ;
RIERA, J ;
VIADEL, L .
TETRAHEDRON LETTERS, 1994, 35 (35) :6529-6532
[6]
(2,6-Dichlorophenyl)bis(2,4,6-trichlorophenyl)methyl radical. Synthesis, magnetic behaviour and crystal structure [J].
Carilla, J ;
Fajari, L ;
Julia, L ;
Sane, J ;
Rius, J .
TETRAHEDRON, 1996, 52 (20) :7013-7024
[7]
Oxidant Activity of Tris(2,4,6-trichloro-3,5-dinitrophenyl)methyl Radical with Catechol and Pyrogallol. Mechanistic Considerations [J].
Carreras, Anna ;
Esparbe, Isaac ;
Brillas, Enric ;
Rius, Jordi ;
Torres, Josep Lluis ;
Julia, Luis .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (06) :2368-2373
[8]
DULOG D, 1996, PUBLIC EPR SOFTWARE
[9]
[4-(N-carbazolyl)-2,6-dichlorophenyl]bis(2,4,6-trichlorophenyl)methyl radical an efficient red light-emitting paramagnetic molecule [J].
Gamero, V ;
Velasco, D ;
Latorre, S ;
López-Calahorra, F ;
Brillas, E ;
Juliá, L .
TETRAHEDRON LETTERS, 2006, 47 (14) :2305-2309
[10]
Quantitative kinetic analysis of hydrogen transfer reactions from dietary polyphenols to the DPPH radical [J].
Goupy, P ;
Dufour, C ;
Loonis, M ;
Dangles, O .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2003, 51 (03) :615-622