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dc.creatorMarkovic, Violeta
dc.creatorMarković, Svetlana
dc.creatorJanicijevic, Ana
dc.creatorRodić, Marko V.
dc.creatorLeovac, Vukadin
dc.creatorTodorović, Nina
dc.creatorTrifunović, Snežana
dc.creatorJoksovic, Milan D.
dc.date.accessioned2019-01-30T17:35:10Z
dc.date.available2019-01-30T17:35:10Z
dc.date.issued2013
dc.identifier.issn1040-0400
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/1225
dc.description.abstractA study on the synthesis and mechanistical aspects of formation of 3-methyl-5-oxo-3-pyrazolin-1-carboxamide (MOPC) starting from S-methylisothiosemicarbazide hydrogen iodide and methyl acetoacetate was performed. In the alkaline aqueous solution, the intermediate methyl acetoacetate S-methylisothiosemicarbazone undergoes substitution of CH3S- anion by hydroxide anion, cyclization, carbanion formation, and elimination of methanol, thus yielding corresponding Na-enolate salt of pyrazol-5-one derivative. The structure of the compound obtained after protonation of the formed enolate salt was determined by means of spectroscopic techniques and single-crystal X-ray diffraction analysis. The mechanism of conversion of methyl acetoacetate S-methylisothiosemicarbazone into MOPC was investigated by means of the B3LYP functional, and it was found that the reaction is thermodynamically controlled.en
dc.publisherSpringer/Plenum Publishers, New York
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172016/RS//
dc.rightsrestrictedAccess
dc.sourceStructural Chemistry
dc.subjectPyrazoloneen
dc.subjectReaction mechanismen
dc.subjectDFTen
dc.subjectThermodynamic and kinetic controlen
dc.titleMechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetateen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractРодић, Марко В.; Марковиц, Виолета; Леовац, Вукадин М.; Јаницијевиц, Aна; Тодоровић, Нина; Марковић, Светлана; Јоксовиц, Милан Д.; Трифуновиц, Снезана;
dc.citation.volume24
dc.citation.issue6
dc.citation.spage2127
dc.citation.epage2136
dc.citation.other24(6): 2127-2136
dc.citation.rankM22
dc.identifier.doi10.1007/s11224-013-0223-3
dc.identifier.rcubConv_3080
dc.identifier.scopus2-s2.0-84889098809
dc.identifier.wos000328326800034
dc.type.versionpublishedVersion


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