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Article: Modeling SN2 reactions in methanol solution by ab initio calculation of nucleophile solvent-substrate clusters

TitleModeling SN2 reactions in methanol solution by ab initio calculation of nucleophile solvent-substrate clusters
Authors
Issue Date2005
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2005, v. 70 n. 23, p. 9279-9287 How to Cite?
AbstractAb initio calculations were used to study the S N2 reactions of the CH 3OCH 2I molecule with a methoxide ion (CH 3O -) and a methanol molecule by systematically building up the reaction system with explicit incorporation of the methanol solvent molecules. For the reaction of CH 3OCH 2I with a methoxide ion, the explicit incorporation of the methanol molecules to better solvate the methoxide ion led to an increase in the barrier to reaction. For the reaction of CH 3OCH 2I with a methanol molecule, the explicit incorporation of the methanol molecules led to a decrease in the barrier to reaction because of an inclination of this reaction to proceed with the nucleophilic displacements accompanied by proton transfer through the H-bonding chain. The H-bonding chain served as both acid and base catalysts for the displacement reaction. A ca. 10 15-fold acceleration of the methanol tetramer incorporated S N2 reaction was predicted relative to the corresponding methanol monomer reaction. The properties of the reactions examined are discussed briefly. © 2005 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/167968
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.authorZhao, Cen_US
dc.contributor.authorPhillips, DLen_US
dc.date.accessioned2012-10-08T03:13:32Z-
dc.date.available2012-10-08T03:13:32Z-
dc.date.issued2005en_US
dc.identifier.citationJournal Of Organic Chemistry, 2005, v. 70 n. 23, p. 9279-9287en_US
dc.identifier.issn0022-3263en_US
dc.identifier.urihttp://hdl.handle.net/10722/167968-
dc.description.abstractAb initio calculations were used to study the S N2 reactions of the CH 3OCH 2I molecule with a methoxide ion (CH 3O -) and a methanol molecule by systematically building up the reaction system with explicit incorporation of the methanol solvent molecules. For the reaction of CH 3OCH 2I with a methoxide ion, the explicit incorporation of the methanol molecules to better solvate the methoxide ion led to an increase in the barrier to reaction. For the reaction of CH 3OCH 2I with a methanol molecule, the explicit incorporation of the methanol molecules led to a decrease in the barrier to reaction because of an inclination of this reaction to proceed with the nucleophilic displacements accompanied by proton transfer through the H-bonding chain. The H-bonding chain served as both acid and base catalysts for the displacement reaction. A ca. 10 15-fold acceleration of the methanol tetramer incorporated S N2 reaction was predicted relative to the corresponding methanol monomer reaction. The properties of the reactions examined are discussed briefly. © 2005 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.titleModeling SN2 reactions in methanol solution by ab initio calculation of nucleophile solvent-substrate clustersen_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.doi10.1021/jo051280+en_US
dc.identifier.pmid16268600-
dc.identifier.scopuseid_2-s2.0-27744591618en_US
dc.identifier.hkuros117008-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-27744591618&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume70en_US
dc.identifier.issue23en_US
dc.identifier.spage9279en_US
dc.identifier.epage9287en_US
dc.identifier.isiWOS:000233209400023-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridLin, X=35205535200en_US
dc.identifier.scopusauthoridZhao, C=7403563836en_US
dc.identifier.scopusauthoridPhillips, DL=7404519365en_US

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