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Article: Density functional theory study of water-assisted deprotonation of the C8 intermediate in the reaction of the 2-fluorenylnitrenium ion with guanosine to form a C8 adduct

TitleDensity functional theory study of water-assisted deprotonation of the C8 intermediate in the reaction of the 2-fluorenylnitrenium ion with guanosine to form a C8 adduct
Authors
KeywordsCatalysis
Density functional theory
Deprotonation
Guanosine
Nitrenium ion
Water
Issue Date2008
PublisherElsevier BV. The Journal's web site is located at http://www.elsevier.com/locate/theochem
Citation
Journal Of Molecular Structure: Theochem, 2008, v. 848 n. 1-3, p. 119-127 How to Cite?
AbstractA density functional theory study of the deprotonation reaction of the "C8 intermediate (8-(2-fluorenylamino)-guanosine cation)", which is the intermediate of reaction of 2-fluorenylnitrenium ion with guanosine, to produce the C8 adduct final product is described. The barrier to reaction is high in the gas phase and becomes substantially lower when explicit hydrogen bonding of water molecules is considered. This is consistent with the experimentally observed decay of the "C8 intermediate" on the millisecond time scale. Bulk solvent effects caused only moderate changes in the barrier to reaction in the deprotonation reaction systems that include water molecules. Thus, the hydrogen bonding of the water molecules appears to account for most of the differences between the gas phase and aqueous solution barriers for the deprotonation reaction of the C8 intermediate to form the C8 adduct product. These results suggest that a water-assisted deprotonation mechanism transforms the "C8 intermediate" into the C8 adduct final product in the reactions of arylnitrenium ions with guanine derivatives in aqueous environments. © 2007 Elsevier B.V. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/69495
ISSN
2012 Impact Factor: 1.371
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorGuo, Zen_HK
dc.contributor.authorLin, Xen_HK
dc.contributor.authorZhao, Cen_HK
dc.contributor.authorPhillips, DLen_HK
dc.date.accessioned2010-09-06T06:14:11Z-
dc.date.available2010-09-06T06:14:11Z-
dc.date.issued2008en_HK
dc.identifier.citationJournal Of Molecular Structure: Theochem, 2008, v. 848 n. 1-3, p. 119-127en_HK
dc.identifier.issn0166-1280en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69495-
dc.description.abstractA density functional theory study of the deprotonation reaction of the "C8 intermediate (8-(2-fluorenylamino)-guanosine cation)", which is the intermediate of reaction of 2-fluorenylnitrenium ion with guanosine, to produce the C8 adduct final product is described. The barrier to reaction is high in the gas phase and becomes substantially lower when explicit hydrogen bonding of water molecules is considered. This is consistent with the experimentally observed decay of the "C8 intermediate" on the millisecond time scale. Bulk solvent effects caused only moderate changes in the barrier to reaction in the deprotonation reaction systems that include water molecules. Thus, the hydrogen bonding of the water molecules appears to account for most of the differences between the gas phase and aqueous solution barriers for the deprotonation reaction of the C8 intermediate to form the C8 adduct product. These results suggest that a water-assisted deprotonation mechanism transforms the "C8 intermediate" into the C8 adduct final product in the reactions of arylnitrenium ions with guanine derivatives in aqueous environments. © 2007 Elsevier B.V. All rights reserved.en_HK
dc.languageengen_HK
dc.publisherElsevier BV. The Journal's web site is located at http://www.elsevier.com/locate/theochemen_HK
dc.relation.ispartofJournal of Molecular Structure: THEOCHEMen_HK
dc.rightsJournal of Molecular Structure: THEOCHEM. Copyright © Elsevier BV.en_HK
dc.subjectCatalysisen_HK
dc.subjectDensity functional theoryen_HK
dc.subjectDeprotonationen_HK
dc.subjectGuanosineen_HK
dc.subjectNitrenium ionen_HK
dc.subjectWateren_HK
dc.titleDensity functional theory study of water-assisted deprotonation of the C8 intermediate in the reaction of the 2-fluorenylnitrenium ion with guanosine to form a C8 adducten_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0166-1280&volume=848&spage=119&epage=127&date=2008&atitle=Density+Functional+Theory+Study+of+Water-assisted+Deprotonation+of+the+C8+Intermediate+in+the+Reaction+of+the+2-Fluorenylnitrenium+Ion+with+Guanosine+to+form+a+C8+Adducten_HK
dc.identifier.emailPhillips, DL:phillips@hku.hken_HK
dc.identifier.authorityPhillips, DL=rp00770en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/j.theochem.2007.09.017en_HK
dc.identifier.scopuseid_2-s2.0-37349110818en_HK
dc.identifier.hkuros151576en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-37349110818&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume848en_HK
dc.identifier.issue1-3en_HK
dc.identifier.spage119en_HK
dc.identifier.epage127en_HK
dc.identifier.isiWOS:000253132400016-
dc.publisher.placeNetherlandsen_HK
dc.identifier.scopusauthoridGuo, Z=36554069300en_HK
dc.identifier.scopusauthoridLin, X=35205535200en_HK
dc.identifier.scopusauthoridZhao, C=7403563836en_HK
dc.identifier.scopusauthoridPhillips, DL=7404519365en_HK

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