File Download

There are no files associated with this item.

  Links for fulltext
     (May Require Subscription)
Supplementary

Article: Investigation of the Role of Protonation of Benzophenone and Its Derivatives in Acidic Aqueous Solutions Using Time-Resolved Resonance Raman Spectroscopy: How Are Ketyl Radicals Formed in Aqueous Solutions?

TitleInvestigation of the Role of Protonation of Benzophenone and Its Derivatives in Acidic Aqueous Solutions Using Time-Resolved Resonance Raman Spectroscopy: How Are Ketyl Radicals Formed in Aqueous Solutions?
Authors
Issue Date2015
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journal/jpcbfk
Citation
The Journal of Physical Chemistry Part B: Condensed Matter, Materials, Surfaces, Interfaces & Biophysical, 2015, v. 119 n. 6, p. 2241–2252 How to Cite?
AbstractThe formation mechanism of ketyl radicals and several other selective photoreactions of benzophenone and its derivatives are initiated by the protonation of their triplet state and have been investigated using nanosecond time-resolved resonance Raman spectroscopy (ns-TR(3)) in solutions of varying conditions. Evidence is found that the ketyl radical is generated by the combined action of a ketone protonation and a subsequent electron transfer based on the results from previous studies on the photochemistry and photophysics of benzophenone and the ns-TR(3) results reported here for benzophenone, 1,4-dibenzoylbenzene, 3-(hydroxymethyl)benzophenone, and ketoprofen in neutral and acidic solution. In order to better understand the role of the protonated ketone, results are summarized for some selective photochemical reactions of benzophenone and its derivatives induced by protonation in acidic solutions. For the parent benzophenone, the protonation of the ketone leads to the photohydration reactions at the ortho- and meta-positions of the benzene ring in acidic aqueous solutions. For 3-(hydroxymethyl)benzophenone, the protonation promotes an interesting photoredox reaction to become very efficient and the predominant reaction in a pH = 2 aqueous solution. While for ketoprofen, the protonation can initiate a solvent-mediated excited-state intramolecular proton transfer (ESIPT) from the carboxyl group to the carbonyl group that then leads to a decarboxylation reaction in a pH = 0 acidic aqueous solution. We briefly discuss the key role of the protonation of the ketone in the photochemistry of these aromatic ketones.
Persistent Identifierhttp://hdl.handle.net/10722/211707
ISSN
2015 Impact Factor: 3.187
2015 SCImago Journal Rankings: 1.414

 

DC FieldValueLanguage
dc.contributor.authorLi, MD-
dc.contributor.authorHuang, J-
dc.contributor.authorLiu, M-
dc.contributor.authorLi, S-
dc.contributor.authorMa, J-
dc.contributor.authorPhillips, DL-
dc.date.accessioned2015-07-21T02:08:32Z-
dc.date.available2015-07-21T02:08:32Z-
dc.date.issued2015-
dc.identifier.citationThe Journal of Physical Chemistry Part B: Condensed Matter, Materials, Surfaces, Interfaces & Biophysical, 2015, v. 119 n. 6, p. 2241–2252-
dc.identifier.issn1520-6106-
dc.identifier.urihttp://hdl.handle.net/10722/211707-
dc.description.abstractThe formation mechanism of ketyl radicals and several other selective photoreactions of benzophenone and its derivatives are initiated by the protonation of their triplet state and have been investigated using nanosecond time-resolved resonance Raman spectroscopy (ns-TR(3)) in solutions of varying conditions. Evidence is found that the ketyl radical is generated by the combined action of a ketone protonation and a subsequent electron transfer based on the results from previous studies on the photochemistry and photophysics of benzophenone and the ns-TR(3) results reported here for benzophenone, 1,4-dibenzoylbenzene, 3-(hydroxymethyl)benzophenone, and ketoprofen in neutral and acidic solution. In order to better understand the role of the protonated ketone, results are summarized for some selective photochemical reactions of benzophenone and its derivatives induced by protonation in acidic solutions. For the parent benzophenone, the protonation of the ketone leads to the photohydration reactions at the ortho- and meta-positions of the benzene ring in acidic aqueous solutions. For 3-(hydroxymethyl)benzophenone, the protonation promotes an interesting photoredox reaction to become very efficient and the predominant reaction in a pH = 2 aqueous solution. While for ketoprofen, the protonation can initiate a solvent-mediated excited-state intramolecular proton transfer (ESIPT) from the carboxyl group to the carbonyl group that then leads to a decarboxylation reaction in a pH = 0 acidic aqueous solution. We briefly discuss the key role of the protonation of the ketone in the photochemistry of these aromatic ketones.-
dc.languageeng-
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journal/jpcbfk-
dc.relation.ispartofThe Journal of Physical Chemistry Part B: Condensed Matter, Materials, Surfaces, Interfaces & Biophysical-
dc.titleInvestigation of the Role of Protonation of Benzophenone and Its Derivatives in Acidic Aqueous Solutions Using Time-Resolved Resonance Raman Spectroscopy: How Are Ketyl Radicals Formed in Aqueous Solutions?-
dc.typeArticle-
dc.identifier.emailLi, MD: mdli@hku.hk-
dc.identifier.emailMa, J: majiani@hku.hk-
dc.identifier.emailPhillips, DL: phillips@hku.hk-
dc.identifier.authorityPhillips, DL=rp00770-
dc.identifier.doi10.1021/jp505954d-
dc.identifier.pmid25141023-
dc.identifier.hkuros244754-
dc.identifier.volume119-
dc.identifier.issue6-
dc.identifier.spage2241-
dc.identifier.epage2252-
dc.publisher.placeUnited States-

Export via OAI-PMH Interface in XML Formats


OR


Export to Other Non-XML Formats