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Title: Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate
Authors: Marković, Violeta
Markovic, Svetlana
Janicijevic A.
Rodic, Marko
Leovac V.
Todorovic N.
Trifunović, Snežana
Joksović, Milan
Issue Date: 2013
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 CH 3S- 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. © 2013 Springer Science+Business Media New York.
Type: article
DOI: 10.1007/s11224-013-0223-3
ISSN: 1040-0400
SCOPUS: 2-s2.0-84889098809
Appears in Collections:Faculty of Science, Kragujevac

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