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Article: Time-Resolved Spectroscopic Study of a Photoinduced Intramolecular Chloride Exchange Reaction of 3 ',5 '-Dimethoxybenzoin Chloride

TitleTime-Resolved Spectroscopic Study of a Photoinduced Intramolecular Chloride Exchange Reaction of 3 ',5 '-Dimethoxybenzoin Chloride
Authors
Issue Date13-Feb-2023
PublisherAmerican Chemical Society
Citation
Journal of Physical Chemistry B (Soft Condensed Matter and Biophysical Chemistry), 2023, v. 127, n. 7, p. 1645-1651 How to Cite?
AbstractPhotoremovable protecting groups are of great importance due to their remote control over the liberation of diverse reactive species temporally and spatially, including biologically active compounds and functional groups. Here, an in-depth investigation on the heterolysis-solvolysis reaction mechanisms of a photoremovable protecting group, 3 ',5 ' dimethoxybenzoin (DMB) chloride, has been accomplished. With the aid of transient absorption and time-resolved resonance Raman spectroscopies, the features of the intermediates that emerged from the photolysis process were directly observed. Elaborate optical and theoretical studies on DMB chloride have suggested a long-lived alpha-keto cation intermediate (0.9 ms) exists as a key intermediate, unlike the radical intermediates that are typically generated in such photocyclization reactions. After undergoing nucleophilic addition and isomerization, the intermediate species eventually leads to the formation of the final product(s).
Persistent Identifierhttp://hdl.handle.net/10722/333945
ISSN
2023 Impact Factor: 2.8
2023 SCImago Journal Rankings: 0.760
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorLi, YC-
dc.contributor.authorZhang, QD-
dc.contributor.authorLo, KC-
dc.contributor.authorYan, ZP-
dc.contributor.authorPhillips, DL-
dc.contributor.authorTang, WJ-
dc.contributor.authorDu, LL-
dc.date.accessioned2023-10-10T03:14:47Z-
dc.date.available2023-10-10T03:14:47Z-
dc.date.issued2023-02-13-
dc.identifier.citationJournal of Physical Chemistry B (Soft Condensed Matter and Biophysical Chemistry), 2023, v. 127, n. 7, p. 1645-1651-
dc.identifier.issn1520-6106-
dc.identifier.urihttp://hdl.handle.net/10722/333945-
dc.description.abstractPhotoremovable protecting groups are of great importance due to their remote control over the liberation of diverse reactive species temporally and spatially, including biologically active compounds and functional groups. Here, an in-depth investigation on the heterolysis-solvolysis reaction mechanisms of a photoremovable protecting group, 3 ',5 ' dimethoxybenzoin (DMB) chloride, has been accomplished. With the aid of transient absorption and time-resolved resonance Raman spectroscopies, the features of the intermediates that emerged from the photolysis process were directly observed. Elaborate optical and theoretical studies on DMB chloride have suggested a long-lived alpha-keto cation intermediate (0.9 ms) exists as a key intermediate, unlike the radical intermediates that are typically generated in such photocyclization reactions. After undergoing nucleophilic addition and isomerization, the intermediate species eventually leads to the formation of the final product(s).-
dc.languageeng-
dc.publisherAmerican Chemical Society-
dc.relation.ispartofJournal of Physical Chemistry B (Soft Condensed Matter and Biophysical Chemistry)-
dc.titleTime-Resolved Spectroscopic Study of a Photoinduced Intramolecular Chloride Exchange Reaction of 3 ',5 '-Dimethoxybenzoin Chloride-
dc.typeArticle-
dc.identifier.doi10.1021/acs.jpcb.3c00009-
dc.identifier.pmid36780292-
dc.identifier.scopuseid_2-s2.0-85148354166-
dc.identifier.volume127-
dc.identifier.issue7-
dc.identifier.spage1645-
dc.identifier.epage1651-
dc.identifier.eissn1520-5207-
dc.identifier.isiWOS:000933369300001-
dc.publisher.placeWASHINGTON-
dc.identifier.issnl1520-5207-

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