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Carbenic vs. ionic mechanistic pathway in reaction of cyclohexanone with bromoform
dc.creator | Vitnik, Vesna | |
dc.creator | Vitnik, Željko | |
dc.creator | Juranić, Ivan | |
dc.date.accessioned | 2019-01-30T17:33:18Z | |
dc.date.available | 2019-01-30T17:33:18Z | |
dc.date.issued | 2012 | |
dc.identifier.issn | 1610-2940 | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/1135 | |
dc.description.abstract | The 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.publisher | Springer, New York | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172035/RS// | |
dc.relation | High-Performance Computing Infrastructure for South East Europe's Research Communities European proj | |
dc.rights | restrictedAccess | |
dc.source | Journal of Molecular Modeling | |
dc.subject | Ab initio calculations | en |
dc.subject | Dibromocarbene | en |
dc.subject | Dihaloepoxides | en |
dc.subject | Reaction mechanisms | en |
dc.subject | Tribromomethyl carbanion | en |
dc.title | Carbenic vs. ionic mechanistic pathway in reaction of cyclohexanone with bromoform | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Витник, Весна; Јураниц, Иван О.; Витник, Жељко; | |
dc.citation.volume | 18 | |
dc.citation.issue | 10 | |
dc.citation.spage | 4721 | |
dc.citation.epage | 4728 | |
dc.citation.other | 18(10): 4721-4728 | |
dc.citation.rank | M21 | |
dc.identifier.pmid | 22660943 | |
dc.identifier.doi | 10.1007/s00894-012-1468-2 | |
dc.identifier.scopus | 2-s2.0-84870560097 | |
dc.identifier.wos | 000309862000015 | |
dc.type.version | publishedVersion |