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dc.creatorMarković, Violeta
dc.creatorMarković, Svetlana
dc.creatorJanićijević, Ana
dc.creatorRodić, Marko
dc.creatorLeovac, Vukadin M.
dc.creatorTodorović, Nina
dc.creatorTrifunović, Snežana S.
dc.creatorJoksović, Milan D.
dc.date.accessioned2018-11-22T00:24:46Z
dc.date.available2018-11-22T00:24:46Z
dc.date.issued2013
dc.identifier.issn1040-0400
dc.identifier.urihttps://cherry.chem.bg.ac.rs/handle/123456789/1455
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.abstractМарковиц, Светлана; Тодоровиц, Нина; Јоксовиц, Милан Д.; Родиц, Марко В.; Трифуновић, Снежана; Леовац, Вукадин М.; Јаницијевиц, Aна; Марковиц, Виолета;
dc.citation.volume24
dc.citation.issue6
dc.citation.spage2127
dc.citation.epage2136
dc.identifier.wos000328326800034
dc.identifier.doi10.1007/s11224-013-0223-3
dc.citation.other24(6): 2127-2136
dc.citation.rankM22
dc.description.otherSupplementary material: [http://cherry.chem.bg.ac.rs/handle/123456789/3505]
dc.type.versionpublishedVersionen
dc.identifier.scopus2-s2.0-84889098809
dc.identifier.rcubKon_2575


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