10-methylacridine derivatives acting as efficient and stable photocatalysts in reductive dehalogenation of halogenated compounds with sodium borohydride via photoinduced electron transfer
- Osaka Univ. (Japan)
10-Methylacridine derivatives, 9,10-dihydro-10-methylacridine (AcrH{sub 2}) and acriflavine (AFH{sup +}), act as efficient and stable photocatalysts in reductive dechlorination of p-chlorobiphenyl (ClBP) as well as dehalogenation of other halogenated compounds with sodium borohydride (NaBH{sub 4}) in a mixture of acetonitrile and H{sub 2}O (9:1 v/v) at 298 K. The reductive dechlorination proceeds via the reduction of ClBP by the singlet excited state ({sup 1}AcrH{sub 2}*) to yield dechlorinated product (biphenyl) and 10-methylacridinium ion (AcrH{sup +}), followed by the facile reduction of AcrH{sup +} with NaBH{sub 4} to regenerate AcrH{sub 2}. The absence of the primary kinetic isotope effect as well as the comparison of the observed rate constants with those predicted by using the Marcus theory of electron transfer indicates that the reduction of halogenated compounds (RX) by the singlet excited state ({sup 1}AcrH{sub 2}*) proceeds via photoinduced electron transfer from {sup 1}AcrH{sub 2}* to RX, which results in the cleavage of C-X bonds.
- OSTI ID:
- 5169014
- Journal Information:
- Journal of the American Chemical Society; (United States), Vol. 112:24; ISSN 0002-7863
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
CHLORINATED AROMATIC HYDROCARBONS
DEHALOGENATION
ELECTRON TRANSFER
EXPERIMENTAL DATA
MEDIUM TEMPERATURE
PHOTOCHEMICAL REACTIONS
AROMATICS
CHEMICAL REACTIONS
DATA
HALOGENATED AROMATIC HYDROCARBONS
INFORMATION
NUMERICAL DATA
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
400500* - Photochemistry