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Kinetics and Mechanism of the Cyclisation of Methyl-(2-cyano-4,6-dinitrophenylsulfanyl) acetate Producing Methyl-3-amino-5,7-dinitro-benzo[b]thiophene-2-carboxylate
Authors: Pešková Markéta | Hanusek Jiří | Macháček Vladimír
Year: 2004
Type of publication: článek v odborném periodiku
Name of source: Chemical Papers
Publisher name: Springer
Page from-to: 133-138
Titles:
Language Name Abstract Keywords
cze Kinetika a mechanismus cyklizace methyl-(2-kyan-4,6-dinitrofenylsulfanyl)acetatu poskytující methyl-3-amino-5,7-dinitro-benzo[b]thiophene-2-karboxylát Bazicky katalyzovaná cyklizace methyl-(2-kyan-4,6-dinitrofenylsulfanyl)acetátu poskytuje methyl-3-amino-5,7-dinitrobenzo[b]thiofen-2-karboxylát. To znamená, že vytvořený karbaniont přednostně atakuje kyan skupinu a nikoliv nitro skupinu. Kinetika této cyklizace byla studována v methanolických terciárních aminových pufrech a byl navržen mechanismus. Reakce je předmětem obecné bázické katalýzy. Zjištěná hodnota Bronstedova koeficientu beta = 0.9 ? 0.1 indikuje pozdní tranzitní stav rychlost určujícího proton-transferu.
eng Kinetics and Mechanism of the Cyclisation of Methyl-(2-cyano-4,6-dinitrophenylsulfanyl) acetate Producing Methyl-3-amino-5,7-dinitro-benzo[b]thiophene-2-carboxylate Base-catalysed ring closure of methyl-(2-cyano-4,6-dinitrophenylsulfanyl) acetate produces methyl-3-amino-5,7-dinitrobenzo[b]thiophene-2-carboxylate. This means that the carbanion initially formed attacks cyano group and not nitro group. The kinetics of this cyclisation reaction has been studied in methanolic buffers of tert-amine/tert-ammonium chloride, and the reaction mechanism was suggested. The reaction is subject to general base catalysis. The found value of the Brřnsted coefficient is beta = 0.9 ? 0.1, which indicates a late transition state of the rate-limiting proton transfer. Kinetics, mechanism methyl-(2-cyano-4,6-dinitrophenylsulfanyl) acetate, methyl-3-amino-5,7-dinitro-benzo[b]thiophene-2-carboxylate,

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