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dc.creatorVitnik, Vesna
dc.creatorVitnik, Željko
dc.creatorJuranić, Ivan
dc.date.accessioned2019-01-30T17:33:18Z
dc.date.available2019-01-30T17:33:18Z
dc.date.issued2012
dc.identifier.issn1610-2940
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/1135
dc.description.abstractThe extensive computation study was done to elucidate the mechanism of formation dibromoepoxide from cyclohexanone and bromoform. In this reaction, the formation of dihaloepoxide 2 is postulated as a key step that determines the distribution and stereochemistry of products. Two mechanistic paths of reaction were investigated: the addition of dibromocarbene to carbonyl group of ketone, and the addition of tribromomethyl carbanion to the same (C=O) group. The mechanisms for the addition reactions of dibromocarbenes and tribromomethyl carbanions with cyclohexanone have been investigated using ab initio HF/6-311++G** and MP2/6-311+G* level of theory. Solvent effects on these reactions have been explored by calculations which included a continuum polarizable conductor model (CPCM) for the solvent (H2O). The calculations showed that both mechanisms are possible and are exothermic, but have markedly different activation energies.en
dc.publisherSpringer, New York
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172035/RS//
dc.relationHigh-Performance Computing Infrastructure for South East Europe's Research Communities European proj
dc.rightsrestrictedAccess
dc.sourceJournal of Molecular Modeling
dc.subjectAb initio calculationsen
dc.subjectDibromocarbeneen
dc.subjectDihaloepoxidesen
dc.subjectReaction mechanismsen
dc.subjectTribromomethyl carbanionen
dc.titleCarbenic vs. ionic mechanistic pathway in reaction of cyclohexanone with bromoformen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractВитник, Весна; Јураниц, Иван О.; Витник, Жељко;
dc.citation.volume18
dc.citation.issue10
dc.citation.spage4721
dc.citation.epage4728
dc.citation.other18(10): 4721-4728
dc.citation.rankM21
dc.identifier.pmid22660943
dc.identifier.doi10.1007/s00894-012-1468-2
dc.identifier.rcubConv_2869
dc.identifier.scopus2-s2.0-84870560097
dc.identifier.wos000309862000015
dc.type.versionpublishedVersion


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