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A DFT Study on the Mechanism of the Annulation Reaction of Trichloronitroethylene with Aniline in the Synthesis of Quinoxalinone-N-oxides

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dc.contributor.authorERDEM, SAFİYE
dc.contributor.authorsOzpinar, Gul A.; Erdem, Safiye S.; Meyer, Christian; Kaufmann, Dieter E.
dc.date.accessioned2022-03-12T17:38:10Z
dc.date.available2022-03-12T17:38:10Z
dc.date.issued2009
dc.description.abstractThe new annulation reaction of trichloronitroethylene with aniline results in the formation of a quinoxalinone-N-oxide derivative. The mechanism of this one-pot annulation reaction between trichloronitroethylene (TCNiE) and anilines has been extensively investigated with B3LYP/6-31+G** methodology. Five different paths (1-5) were proposed and modeled by using this method. These paths were compared in terms of the activation energies of their rate-determining steps and in regard to the experimental findings. Paths 3 and 5, proceeding via four-membered heterocyclic rings, were found to be the most plausible paths with activation energies of 32 and 29 kcal/mol for the rate-determining steps, respectively. The effects of substituent, solvent, temperature, and computational method on these steps were also investigated. The results showed that path 5 is the most plausible mechanism for the annulation reaction of trichloronitroethylene with aniline.
dc.identifier.doi10.1021/jo9003629
dc.identifier.issn0022-3263
dc.identifier.pubmed19558178
dc.identifier.urihttps://hdl.handle.net/11424/229455
dc.identifier.wosWOS:000267432700009
dc.language.isoeng
dc.publisherAMER CHEMICAL SOC
dc.relation.ispartofJOURNAL OF ORGANIC CHEMISTRY
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectDENSITY-FUNCTIONAL THERMOCHEMISTRY
dc.subjectTRANSITION-STATE GEOMETRIES
dc.subjectPOLYHALOGENATED NITROBUTADIENES
dc.subjectADJUSTABLE-PARAMETERS
dc.subjectACTIVATION-ENERGIES
dc.subjectBIOLOGICAL-ACTIVITY
dc.subjectBARRIER HEIGHTS
dc.subjectEXACT-EXCHANGE
dc.subjectDERIVATIVES
dc.subjectCHEMISTRY
dc.titleA DFT Study on the Mechanism of the Annulation Reaction of Trichloronitroethylene with Aniline in the Synthesis of Quinoxalinone-N-oxides
dc.typearticle
dspace.entity.typePublication
local.avesis.id051a1bc7-9175-4eb4-bac1-570d56ca43d6
local.import.packageSS17
local.indexed.atWOS
local.indexed.atSCOPUS
local.indexed.atPUBMED
local.journal.numberofpages13
oaire.citation.endPage4739
oaire.citation.issue13
oaire.citation.startPage4727
oaire.citation.titleJOURNAL OF ORGANIC CHEMISTRY
oaire.citation.volume74
relation.isAuthorOfPublication99f2f09c-7e48-402f-9bb9-ccdd73c27ec2
relation.isAuthorOfPublication.latestForDiscovery99f2f09c-7e48-402f-9bb9-ccdd73c27ec2

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