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Titolo:
ONE-ELECTRON REDUCTION OF ARENEDIAZONIUM COMPOUNDS BY PHYSIOLOGICAL ELECTRON-DONORS GENERATES ARYL RADICALS - AN EPR AND SPIN-TRAPPING INVESTIGATION
Autore:
RESZKA KJ; CHIGNELL CF;
Indirizzi:
NIEHS,MOLEC BIOPHYS LAB,POB 12233 RES TRIANGLE PK NC 27709
Titolo Testata:
Chemico-biological interactions
fascicolo: 3, volume: 96, anno: 1995,
pagine: 223 - 234
SICI:
0009-2797(1995)96:3<223:OROACB>2.0.ZU;2-L
Fonte:
ISI
Lingua:
ENG
Soggetto:
CUTANEOUS PHOTOSENSITIZING AGENTS; PHOTOLYSIS PRODUCTS; PHOTOCHEMICAL DECOMPOSITION; 4-AMINOBENZOIC ACID; AZO-COMPOUNDS; SALTS; SULFANILAMIDE; PRECURSORS; MECHANISM; IONS;
Keywords:
ARYL RADICALS; DIAZONIUM COMPOUNDS; EPR; SPIN TRAPPING;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Science Citation Index Expanded
Science Citation Index Expanded
Science Citation Index Expanded
Citazioni:
23
Recensione:
Indirizzi per estratti:
Citazione:
K.J. Reszka e C.F. Chignell, "ONE-ELECTRON REDUCTION OF ARENEDIAZONIUM COMPOUNDS BY PHYSIOLOGICAL ELECTRON-DONORS GENERATES ARYL RADICALS - AN EPR AND SPIN-TRAPPING INVESTIGATION", Chemico-biological interactions, 96(3), 1995, pp. 223-234

Abstract

Arenediazonium compounds (ArN2+) are strong oxidizing agents, which upon one-electron reduction decompose, releasing aryl radicals (Ar-.). The present studies were undertaken to determine whether reductive fragmentation of ArN2+ can be induced by biologically relevant electron donors. We found that 4-X-Ph-N-2(+) (where X: -NO2, -Br, -Cl, -OMe and -N(Et)(2)) decomposes to the respective aryl radicals when reduced by ascorbate, NADH, potassium ferrocyanide, catechol or p-hydroquinone inaqueous solutions. Radical identification was based on analysis of the EPR spectra of spin adducts formed by reaction of these radicals with spin traps 2-methyl-2-nitrosopropane (MNP), 3,5-dibromo-4-nitrosobenzene sulphonate (DBNBS) or 5,5-dimethyl-1-pyrroline N-oxide (DMPO). This study shows that reduction of arenediazonium ions can be a convenient method for generating aryl radicals in aqueous solutions, In addition, this investigation confirms that biological reducing agents are capable of inducing fragmentation of ArN2+ into aryl radicals. This reaction may be pertinent to some biological actions of arenediazonium compounds.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 23/09/20 alle ore 15:24:31