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- Publisher Website: 10.1021/jo702011z
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- PMID: 18092803
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Article: Reaction mechanism and stereoselectivity of ruthenium-porphyrin-catalyzed intramolecular amidation of sulfamate ester: A DFT computational study
Title | Reaction mechanism and stereoselectivity of ruthenium-porphyrin-catalyzed intramolecular amidation of sulfamate ester: A DFT computational study |
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Authors | |
Issue Date | 2008 |
Publisher | American 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 Identifier | http://hdl.handle.net/10722/168284 |
ISSN | 2023 Impact Factor: 3.3 2023 SCImago Journal Rankings: 0.724 |
ISI Accession Number ID | |
References |
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Lin, X | en_US |
dc.contributor.author | Che, CM | en_US |
dc.contributor.author | Phillips, DL | en_US |
dc.date.accessioned | 2012-10-08T03:17:01Z | - |
dc.date.available | 2012-10-08T03:17:01Z | - |
dc.date.issued | 2008 | en_US |
dc.identifier.citation | Journal Of Organic Chemistry, 2008, v. 73 n. 2, p. 529-537 | en_US |
dc.identifier.issn | 0022-3263 | en_US |
dc.identifier.uri | http://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.language | eng | en_US |
dc.publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc | en_US |
dc.relation.ispartof | Journal of Organic Chemistry | en_US |
dc.subject.mesh | Amides - Chemistry | en_US |
dc.subject.mesh | Catalysis | en_US |
dc.subject.mesh | Computer Simulation | en_US |
dc.subject.mesh | Esters - Chemistry | en_US |
dc.subject.mesh | Models, Chemical | en_US |
dc.subject.mesh | Molecular Structure | en_US |
dc.subject.mesh | Organometallic Compounds - Chemistry | en_US |
dc.subject.mesh | Porphyrins - Chemistry | en_US |
dc.subject.mesh | Ruthenium - Chemistry | en_US |
dc.subject.mesh | Stereoisomerism | en_US |
dc.subject.mesh | Sulfonic Acids - Chemistry | en_US |
dc.title | Reaction mechanism and stereoselectivity of ruthenium-porphyrin-catalyzed intramolecular amidation of sulfamate ester: A DFT computational study | en_US |
dc.type | Article | en_US |
dc.identifier.email | Che, CM:cmche@hku.hk | en_US |
dc.identifier.email | Phillips, DL:phillips@hku.hk | en_US |
dc.identifier.authority | Che, CM=rp00670 | en_US |
dc.identifier.authority | Phillips, DL=rp00770 | en_US |
dc.description.nature | link_to_subscribed_fulltext | en_US |
dc.identifier.doi | 10.1021/jo702011z | en_US |
dc.identifier.pmid | 18092803 | - |
dc.identifier.scopus | eid_2-s2.0-40949128193 | en_US |
dc.identifier.hkuros | 147490 | - |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-40949128193&selection=ref&src=s&origin=recordpage | en_US |
dc.identifier.volume | 73 | en_US |
dc.identifier.issue | 2 | en_US |
dc.identifier.spage | 529 | en_US |
dc.identifier.epage | 537 | en_US |
dc.identifier.isi | WOS:000252325200024 | - |
dc.publisher.place | United States | en_US |
dc.identifier.scopusauthorid | Lin, X=35205535200 | en_US |
dc.identifier.scopusauthorid | Che, CM=7102442791 | en_US |
dc.identifier.scopusauthorid | Phillips, DL=7404519365 | en_US |
dc.identifier.issnl | 0022-3263 | - |