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Article: Time-resolved resonance raman and density functional theory investigation of the photochemistry of (s)-ketoprofen

TitleTime-resolved resonance raman and density functional theory investigation of the photochemistry of (s)-ketoprofen
Authors
Issue Date2009
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journal/jpcbfk
Citation
Journal Of Physical Chemistry B, 2009, v. 113 n. 30, p. 10530-10539 How to Cite?
AbstractKetoprofen is known to induce photosensitivity due to its specific structure and electronic features, and this limits its use in medical applications. In this Article, the photochemistry of (S)-ketoprofen has been investigated by time-resolved resonance Raman spectroscopy to gain additional information so as to better elucidate the possible photochemical reaction mechanism of ketoprofen in different solvents. In nonaqueous solvents like neat acetonitrile and isopropyl alcohol, and 1:1 acetonitrile: water and 1:1 acetonitrile: acidic water aqueous solvents, (S)-ketoprofen exhibits benzophenone-like photochemistry to produce a triplet state, which in turn produces a ketyl radical-like species that then undergoes a cross-coupling reaction with either a dimethyl radical (which is generated by hydrogen abstraction of isopropyl alcohol) or a water molecule, respectively, at the para-position to form a transient species that has a lifetime up to the microsecond time scale. However, photolysis of (S)-ketoprofen in a 1:1 acetonitrile: alkaline water solution and 3:7 acetonitrile: phosphate buffered solution appears to undergo a prompt decarboxylation reaction. Only one species was observed in the nanosecond time-resolved resonance Raman experiments under these conditions, and this species was tentatively assigned to be a triplet protonated biradical carbanion. © 2009 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/168392
ISSN
2015 Impact Factor: 3.187
2015 SCImago Journal Rankings: 1.414
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorChuang, YPen_US
dc.contributor.authorXue, Jen_US
dc.contributor.authorDu, Yen_US
dc.contributor.authorLi, Men_US
dc.contributor.authorAn, HYen_US
dc.contributor.authorPhillips, DLen_US
dc.date.accessioned2012-10-08T03:18:22Z-
dc.date.available2012-10-08T03:18:22Z-
dc.date.issued2009en_US
dc.identifier.citationJournal Of Physical Chemistry B, 2009, v. 113 n. 30, p. 10530-10539en_US
dc.identifier.issn1520-6106en_US
dc.identifier.urihttp://hdl.handle.net/10722/168392-
dc.description.abstractKetoprofen is known to induce photosensitivity due to its specific structure and electronic features, and this limits its use in medical applications. In this Article, the photochemistry of (S)-ketoprofen has been investigated by time-resolved resonance Raman spectroscopy to gain additional information so as to better elucidate the possible photochemical reaction mechanism of ketoprofen in different solvents. In nonaqueous solvents like neat acetonitrile and isopropyl alcohol, and 1:1 acetonitrile: water and 1:1 acetonitrile: acidic water aqueous solvents, (S)-ketoprofen exhibits benzophenone-like photochemistry to produce a triplet state, which in turn produces a ketyl radical-like species that then undergoes a cross-coupling reaction with either a dimethyl radical (which is generated by hydrogen abstraction of isopropyl alcohol) or a water molecule, respectively, at the para-position to form a transient species that has a lifetime up to the microsecond time scale. However, photolysis of (S)-ketoprofen in a 1:1 acetonitrile: alkaline water solution and 3:7 acetonitrile: phosphate buffered solution appears to undergo a prompt decarboxylation reaction. Only one species was observed in the nanosecond time-resolved resonance Raman experiments under these conditions, and this species was tentatively assigned to be a triplet protonated biradical carbanion. © 2009 American Chemical Society.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journal/jpcbfken_US
dc.relation.ispartofJournal of Physical Chemistry Ben_US
dc.subject.meshAnti-Inflammatory Agents, Non-Steroidal - Chemistryen_US
dc.subject.meshBenzophenones - Chemistryen_US
dc.subject.meshHydrogen-Ion Concentrationen_US
dc.subject.meshKetoprofen - Chemistryen_US
dc.subject.meshPhotochemical Processesen_US
dc.subject.meshQuantum Theoryen_US
dc.subject.meshSolutionsen_US
dc.subject.meshSolvents - Chemistryen_US
dc.subject.meshSpectrum Analysis, Ramanen_US
dc.subject.meshTime Factorsen_US
dc.subject.meshWater - Chemistryen_US
dc.titleTime-resolved resonance raman and density functional theory investigation of the photochemistry of (s)-ketoprofenen_US
dc.typeArticleen_US
dc.identifier.emailPhillips, DL:phillips@hku.hken_US
dc.identifier.authorityPhillips, DL=rp00770en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/jp903234men_US
dc.identifier.pmid19572660-
dc.identifier.scopuseid_2-s2.0-67651218993en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-67651218993&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume113en_US
dc.identifier.issue30en_US
dc.identifier.spage10530en_US
dc.identifier.epage10539en_US
dc.identifier.isiWOS:000268231000064-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridChuang, YP=23670354300en_US
dc.identifier.scopusauthoridXue, J=23007272500en_US
dc.identifier.scopusauthoridDu, Y=35310175500en_US
dc.identifier.scopusauthoridLi, M=7405265795en_US
dc.identifier.scopusauthoridAn, HY=54411879800en_US
dc.identifier.scopusauthoridPhillips, DL=7404519365en_US

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