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Pregled bibliografske jedinice broj: 454344

Časopis

Autori: Basarić, Nikola; Franco-Cea, Alfredo; Alešković, Marija; Mlinarić-Majerski, Kata; Wan, Peter
Naslov: Photochemical deuterium exchange in phenyl-substituted pyrroles and indoles in CD3CN-D2O
Izvornik: Photochemical & photobiological sciences (1474-905X) 9 (2010), 6; 779-790
Vrsta rada: članak
Ključne riječi: pyrroles; indoles; photochemistry; deuteration; radical cations
Sažetak:
A new mechanism of photochemical deuteration of some phenylpyrroles and indoles is reported. Irradiation of 2-phenylpyrrole (8), 2-phenylindole (9), and 7-phenylindole (12) in CH3CN–D2O gives rise to deuterium exchange at the C-atoms of the heterocycle and the adjacent phenyl ring. Photolysis of indole (7), 8, 9, 12 and N-methyl-2-phenylindole (10) in CD3CN–D2O also leads to deuteration at C-atoms with significantly higher yield. The mechanism most probably involves ejection of an electron on excitation and formation of radical cations that abstract D-atoms from CD3CN or undergo bimolecular D-abstraction (photolysis in CH3CN–D2O). The other possible mechanism of deuterium exchange for 7, 8, 9 and 12 may take place via a homolytic N–D cleavage and recombination of the radical pair. Radical cations of 8, 9 and 10 were detected by laser flash photolysis. Steady state and time-resolved fluorescence of 8, 9, 10 and 12 showed that photoinduced intramolecular electron transfer probably does not occur. The fluorescence was quenched by acid and base and the rate constants determined by Stern–Volmer analyses. The estimated pKa values for the protonation and deprotonation of the singlet excited states indicated that in neutral aqueous solutions ESPT probably does not take place, additionally corroborating the radical or radical cationic mechanism of deuteration.
Projekt / tema: 02.05/25, 098-0982933-2911
Izvorni jezik: ENG
Rad je indeksiran u
bazama podataka:
Current Contents Connect (CCC)
MEDLINE
Scopus
SCI-EXP, SSCI i/ili A&HCI
Science Citation Index Expanded (SCI-EXP) (sastavni dio Web of Science Core Collectiona)
Kategorija: Znanstveni
Znanstvena područja:
Kemija
URL Internet adrese: http://pubs.rsc.org/en/Content/ArticleLanding/2010/PP/B9PP00206E
Broj citata:
Altmetric:
DOI: 10.1039/b9pp00206e
URL cjelovitog teksta:
Google Scholar: Photochemical deuterium exchange in phenyl-substituted pyrroles and indoles in CD3CN-D2O
Upisao u CROSBI: eluksa@irb.hr (eluksa@irb.hr), 29. Ožu. 2010. u 10:18 sati



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