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Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate
dc.creator | Markovic, Violeta | |
dc.creator | Marković, Svetlana | |
dc.creator | Janicijevic, Ana | |
dc.creator | Rodić, Marko V. | |
dc.creator | Leovac, Vukadin | |
dc.creator | Todorović, Nina | |
dc.creator | Trifunović, Snežana | |
dc.creator | Joksovic, Milan D. | |
dc.date.accessioned | 2019-01-30T17:35:10Z | |
dc.date.available | 2019-01-30T17:35:10Z | |
dc.date.issued | 2013 | |
dc.identifier.issn | 1040-0400 | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/1225 | |
dc.description.abstract | A 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.publisher | Springer/Plenum Publishers, New York | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172016/RS// | |
dc.rights | restrictedAccess | |
dc.source | Structural Chemistry | |
dc.subject | Pyrazolone | en |
dc.subject | Reaction mechanism | en |
dc.subject | DFT | en |
dc.subject | Thermodynamic and kinetic control | en |
dc.title | Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Родић, Марко В.; Марковиц, Виолета; Леовац, Вукадин М.; Јаницијевиц, Aна; Тодоровић, Нина; Марковић, Светлана; Јоксовиц, Милан Д.; Трифуновиц, Снезана; | |
dc.citation.volume | 24 | |
dc.citation.issue | 6 | |
dc.citation.spage | 2127 | |
dc.citation.epage | 2136 | |
dc.citation.other | 24(6): 2127-2136 | |
dc.citation.rank | M22 | |
dc.identifier.doi | 10.1007/s11224-013-0223-3 | |
dc.identifier.scopus | 2-s2.0-84889098809 | |
dc.identifier.wos | 000328326800034 | |
dc.type.version | publishedVersion |