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Titolo:
Mechanism of ring opening reaction of 4-benzylidene-2-methyl-5-oxazolone. Part I. Reaction with n-butylamine
Autore:
Betlakowska, B; Banecki, B; Lankiewicz, L; Wiczk, W;
Indirizzi:
Univ Gdansk, Fac Chem, PL-80952 Gdansk, Poland Univ Gdansk Gdansk PolandPL-80952 sk, Fac Chem, PL-80952 Gdansk, Poland Univ Gdansk, Intercollegiate Fac Biotechnol, PL-80822 Gdansk, Poland Univ Gdansk Gdansk Poland PL-80822 c Biotechnol, PL-80822 Gdansk, Poland Med Acad Gdansk, PL-80822 Gdansk, Poland Med Acad Gdansk Gdansk Poland PL-80822 d Gdansk, PL-80822 Gdansk, Poland
Titolo Testata:
POLISH JOURNAL OF CHEMISTRY
fascicolo: 3, volume: 75, anno: 2001,
pagine: 401 - 410
SICI:
0137-5083(200103)75:3<401:MORORO>2.0.ZU;2-Q
Fonte:
ISI
Lingua:
ENG
Soggetto:
PEPTIDE-SYNTHESIS; REACTION SYSTEMS; DISTINGUISHABILITY; IDENTIFIABILITY; BOND;
Keywords:
4-benzylidene-2-methyl-5-oxazolone; n-butylamine; stopped-flow; reaction mechanism; dehydropeptides; kinetics; activation parameters;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
22
Recensione:
Indirizzi per estratti:
Indirizzo: Wiczk, W Univ Gdansk, Fac Chem, Sobieskiego 18, PL-80952 Gdansk, Poland Univ Gdansk Sobieskiego 18 Gdansk Poland PL-80952 Gdansk, Poland
Citazione:
B. Betlakowska et al., "Mechanism of ring opening reaction of 4-benzylidene-2-methyl-5-oxazolone. Part I. Reaction with n-butylamine", POL J CHEM, 75(3), 2001, pp. 401-410

Abstract

The reaction between 4-benzylidene-2-methyl-5-oxazolone (Ox, c = 5.25 x 10(-5) M) with n-butylamine (nBuA, c = 0.026 to 1.66 M) in acetonitrile was studied by UV-Vis spectroscopy using steady-state and stopped-flow apparatus. The amine to Ox molar ratio higher than 500 allows to apply pseudo-first order approximation, whose rate constants depend on amine concentration according to a parabolic equation: k(obs) = 4.63 +/- 0.02 x C-nBuA(2), indicating a complex reaction mechanism. On the other hand, singular value decomposition (SVD) analysis, as well as global analysis of the data obtained fromstopped-flow measurements support a simple A --> B reaction model. Nonlinear dependence of the pseudo-first order rate constant on amine concentration can be explained, assuming that the oxazolone ring opening reaction by n-butylamine in acetonitrile proceeds as parallel reactions: A + B --> C and A+2B --> C. Based on our experimental results and theoretical calculations of the oxazolone ring opening reaction, a mechanism of the reaction between4-benzylidene-2-methyl-5-oxazolone and n-butylamine is proposed.

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Documento generato il 04/12/20 alle ore 16:18:51