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Article: Reaction mechanism and stereoselectivity of ruthenium-porphyrin-catalyzed intramolecular amidation of sulfamate ester: A DFT computational study

TitleReaction mechanism and stereoselectivity of ruthenium-porphyrin-catalyzed intramolecular amidation of sulfamate ester: A DFT computational study
Authors
Issue Date2008
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2008, v. 73 n. 2, p. 529-537 How to Cite?
Abstract(Chemical Equation Presented) The reaction mechanism of the ruthenium-porhyrin complex [Ru(por)(CO)]-catalyzed intramolecular C-H bond amidation was examined using density functional theory (DFT) calculations. The metal-nitrene reactive intermediate, Ru(por)(CO)-NSO3R1 (R1 = 1-methylclohexl-methyl) was found to be highly favorable to generate in terms of the free energy profile from the reaction of the starting materials. Ru(por)(CO)-NSO3R1 may exist in both singlet and triplet states since they are close in energy. In each state, six C-H bond amidation reaction pathways were characterized structurally and energetically. The predicted most probable diastereomeric product out of the four possible diasteromeric products examined in the calculations for the amidation reactions agree well with previously reported experimental results. © 2008 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/168284
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorLin, Xen_US
dc.contributor.authorChe, CMen_US
dc.contributor.authorPhillips, DLen_US
dc.date.accessioned2012-10-08T03:17:01Z-
dc.date.available2012-10-08T03:17:01Z-
dc.date.issued2008en_US
dc.identifier.citationJournal Of Organic Chemistry, 2008, v. 73 n. 2, p. 529-537en_US
dc.identifier.issn0022-3263en_US
dc.identifier.urihttp://hdl.handle.net/10722/168284-
dc.description.abstract(Chemical Equation Presented) The reaction mechanism of the ruthenium-porhyrin complex [Ru(por)(CO)]-catalyzed intramolecular C-H bond amidation was examined using density functional theory (DFT) calculations. The metal-nitrene reactive intermediate, Ru(por)(CO)-NSO3R1 (R1 = 1-methylclohexl-methyl) was found to be highly favorable to generate in terms of the free energy profile from the reaction of the starting materials. Ru(por)(CO)-NSO3R1 may exist in both singlet and triplet states since they are close in energy. In each state, six C-H bond amidation reaction pathways were characterized structurally and energetically. The predicted most probable diastereomeric product out of the four possible diasteromeric products examined in the calculations for the amidation reactions agree well with previously reported experimental results. © 2008 American Chemical Society.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jocen_US
dc.relation.ispartofJournal of Organic Chemistryen_US
dc.subject.meshAmides - Chemistryen_US
dc.subject.meshCatalysisen_US
dc.subject.meshComputer Simulationen_US
dc.subject.meshEsters - Chemistryen_US
dc.subject.meshModels, Chemicalen_US
dc.subject.meshMolecular Structureen_US
dc.subject.meshOrganometallic Compounds - Chemistryen_US
dc.subject.meshPorphyrins - Chemistryen_US
dc.subject.meshRuthenium - Chemistryen_US
dc.subject.meshStereoisomerismen_US
dc.subject.meshSulfonic Acids - Chemistryen_US
dc.titleReaction mechanism and stereoselectivity of ruthenium-porphyrin-catalyzed intramolecular amidation of sulfamate ester: A DFT computational studyen_US
dc.typeArticleen_US
dc.identifier.emailChe, CM:cmche@hku.hken_US
dc.identifier.emailPhillips, DL:phillips@hku.hken_US
dc.identifier.authorityChe, CM=rp00670en_US
dc.identifier.authorityPhillips, DL=rp00770en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/jo702011zen_US
dc.identifier.pmid18092803-
dc.identifier.scopuseid_2-s2.0-40949128193en_US
dc.identifier.hkuros147490-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-40949128193&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume73en_US
dc.identifier.issue2en_US
dc.identifier.spage529en_US
dc.identifier.epage537en_US
dc.identifier.isiWOS:000252325200024-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridLin, X=35205535200en_US
dc.identifier.scopusauthoridChe, CM=7102442791en_US
dc.identifier.scopusauthoridPhillips, DL=7404519365en_US

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