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Photoinduced One-Electron Oxidation of Aromatic Selenides: Effect of the Structure on the Reversible Dimerization Reaction
- Source :
- The Journal of organic chemistry. 83(10)
- Publication Year :
- 2018
-
Abstract
- The photochemical one-electron oxidation of alkyl aryl selenides was studied by means of laser flash photolysis (355 nm). Quenching of the sensitizers in their excited state leads to selenide radical cation in the presence of selenium derivatives. The π-type dimer of methyl phenyl selenide radical cation was detected at 630 nm at expenses of the monomeric radical cation (530 nm). The effect of modification of the aryl and alkyl substituents was also studied, resulting that the formation of dimers depends on both, the electronic properties and steric hindrance of the substituents. Both effects, an increase in steric hindrance in the alkyl moiety or the presence of strongly electron donor groups in the aromatic substituent that stabilizes the radical cation, prevent the dimer formation. Fil: Bouchet, Lydia María. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina Fil: Argüello, Juan Elias. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina
- Subjects :
- Steric effects
chemistry.chemical_classification
SPECTROSCOPY
010405 organic chemistry
Aryl
Organic Chemistry
Substituent
Ciencias Químicas
010402 general chemistry
Photochemistry
01 natural sciences
0104 chemical sciences
RADICAL CATION
chemistry.chemical_compound
SELENIDE
Química Orgánica
chemistry
Radical ion
Selenide
Moiety
Flash photolysis
Alkyl
CIENCIAS NATURALES Y EXACTAS
Subjects
Details
- ISSN :
- 15206904
- Volume :
- 83
- Issue :
- 10
- Database :
- OpenAIRE
- Journal :
- The Journal of organic chemistry
- Accession number :
- edsair.doi.dedup.....459cde103353793a4d141b75f882ce56