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Article: Water concentration dependent photochemistry of ketoprofen in aqueous solutions

TitleWater concentration dependent photochemistry of ketoprofen in aqueous solutions
Authors
Issue Date2010
PublisherRoyal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/pccp
Citation
Physical Chemistry Chemical Physics, 2010, v. 12 n. 18, p. 4800-4808 How to Cite?
AbstractKetoprofen is an important photosensitive drug molecule that has received much attention for the study of its photochemistry in different solvents. In this paper, nanosecond time-resolved resonance Raman spectroscopy was utilized to investigate the photochemistry of ketoprofen in aqueous solutions with varying water concentrations. The rate constants and reaction mechanism of ketoprofen are strongly dependent on the concentration of the solvent. In neat acetonitrile and solvents with low concentrations of water (like water-acetonitrile ≤ 1:1, v/v), ketoprofen exhibits mostly benzophenone-like photochemistry to generate a triplet state which in turn produces a ketyl radical-like species by a hydrogen abstraction reaction. However, in solvents with very high concentrations of water (such as water-acetonitrile ≥ 9:1, v/v), the triplet state ketoprofen is observed first and then undergoes a prompt decarboxylation process to form a triplet protonated biradical carbanion species. For solvents with moderate higher water concentrations (such as between 50% and 90% water by volume), the hydrogen abstraction and decarboxylation processes are two competitive pathways with different rate constants. The triplet state of ketoprofen will simultaneously produce a ketyl radical species and a triplet protonated biradical carbanion species with the amount of each species dependent on the water concentration. © the Owner Societies.
Persistent Identifierhttp://hdl.handle.net/10722/168453
ISSN
2015 Impact Factor: 4.449
2015 SCImago Journal Rankings: 1.836
References

 

DC FieldValueLanguage
dc.contributor.authorLi, MDen_US
dc.contributor.authorDu, Yen_US
dc.contributor.authorChuang, YPen_US
dc.contributor.authorXue, Jen_US
dc.contributor.authorPhillips, DLen_US
dc.date.accessioned2012-10-08T03:19:07Z-
dc.date.available2012-10-08T03:19:07Z-
dc.date.issued2010en_US
dc.identifier.citationPhysical Chemistry Chemical Physics, 2010, v. 12 n. 18, p. 4800-4808en_US
dc.identifier.issn1463-9076en_US
dc.identifier.urihttp://hdl.handle.net/10722/168453-
dc.description.abstractKetoprofen is an important photosensitive drug molecule that has received much attention for the study of its photochemistry in different solvents. In this paper, nanosecond time-resolved resonance Raman spectroscopy was utilized to investigate the photochemistry of ketoprofen in aqueous solutions with varying water concentrations. The rate constants and reaction mechanism of ketoprofen are strongly dependent on the concentration of the solvent. In neat acetonitrile and solvents with low concentrations of water (like water-acetonitrile ≤ 1:1, v/v), ketoprofen exhibits mostly benzophenone-like photochemistry to generate a triplet state which in turn produces a ketyl radical-like species by a hydrogen abstraction reaction. However, in solvents with very high concentrations of water (such as water-acetonitrile ≥ 9:1, v/v), the triplet state ketoprofen is observed first and then undergoes a prompt decarboxylation process to form a triplet protonated biradical carbanion species. For solvents with moderate higher water concentrations (such as between 50% and 90% water by volume), the hydrogen abstraction and decarboxylation processes are two competitive pathways with different rate constants. The triplet state of ketoprofen will simultaneously produce a ketyl radical species and a triplet protonated biradical carbanion species with the amount of each species dependent on the water concentration. © the Owner Societies.en_US
dc.languageengen_US
dc.publisherRoyal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/pccpen_US
dc.relation.ispartofPhysical Chemistry Chemical Physicsen_US
dc.subject.meshAcetonitriles - Chemistryen_US
dc.subject.meshAnti-Inflammatory Agents, Non-Steroidal - Chemistryen_US
dc.subject.meshHydrogen - Chemistryen_US
dc.subject.meshKetoprofen - Chemistryen_US
dc.subject.meshPhotochemical Processesen_US
dc.subject.meshSolutionsen_US
dc.subject.meshSpectrum Analysis, Ramanen_US
dc.subject.meshVibrationen_US
dc.subject.meshWater - Chemistryen_US
dc.titleWater concentration dependent photochemistry of ketoprofen in aqueous solutionsen_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.doi10.1039/b919330hen_US
dc.identifier.pmid20428561-
dc.identifier.scopuseid_2-s2.0-77951823502en_US
dc.identifier.hkuros181785-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-77951823502&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume12en_US
dc.identifier.issue18en_US
dc.identifier.spage4800en_US
dc.identifier.epage4808en_US
dc.publisher.placeUnited Kingdomen_US
dc.identifier.scopusauthoridLi, MD=7405265795en_US
dc.identifier.scopusauthoridDu, Y=35310175500en_US
dc.identifier.scopusauthoridChuang, YP=23670354300en_US
dc.identifier.scopusauthoridXue, J=23007272500en_US
dc.identifier.scopusauthoridPhillips, DL=7404519365en_US
dc.identifier.citeulike7714159-

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