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
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F04%3A00001955" target="_blank" >RIV/00216275:25310/04:00001955 - isvavai.cz</a>
Result on the web
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DOI - Digital Object Identifier
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Alternative languages
Result language
angličtina
Original language name
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
Original language description
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 ofthis 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.
Czech name
Kinetika a mechanismus cyklizace methyl-(2-kyan-4,6-dinitrofenylsulfanyl)acetatu poskytující methyl-3-amino-5,7-dinitro-benzo[b]thiophene-2-karboxylát
Czech description
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.
Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
<a href="/en/project/GA203%2F01%2F0227" target="_blank" >GA203/01/0227: Intramolecular nucleophilic substitution. Extraordinary steric acceleration in a reaction of carbanion with electrophilic centre</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2004
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Chemical Papers
ISSN
0366-6352
e-ISSN
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Volume of the periodical
58
Issue of the periodical within the volume
2
Country of publishing house
SK - SLOVAKIA
Number of pages
6
Pages from-to
133-138
UT code for WoS article
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EID of the result in the Scopus database
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