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Statements

Subject Item
n2:RIV%2F00216275%3A25310%2F05%3A00003027%21RIV08-MSM-25310___
rdf:type
skos:Concept n14:Vysledek
dcterms:description
The kinetics and mechanism of the acid-catalysed hydrolysis of substituted 4-alkyl-4-methyl-2-aryt-4,5-dihydro-1, 3-oxazol-5-ones to the corresponding 2-alkyl-2-benzoylaminopropanoic acids were studied. The Taft correlation of rate constants of the acid-catalysed hydrolysis with alkyl substitution at the 4-position of the 1,3-oxazol-5-one ring is non-linear. In the Hammett correlation, the value of rho to decreases with increasing steric demand of the alkyl substituent. With the 4-isopropyl and tert-butyl derivatives, rho = -0.63 and -0.32, respectively. The protonated 4-isopropyl and tert-butyl derivatives undergo nucleophilic attack by water at the carbonyl carbon atom at the 5-position of the 1,3-oxazol-5-one ring to the extents of ca 70% and 60%, respectively. Another reaction path consists in nucleophilic attack by water at the 2-position of the 1,3-oxazol-5-one ring. The reaction kinetics of aminolyses of substituted 4-isopropyl-4-methyl-2-phenyl-1,3-oxazol-5(4H)-ones (1a, 1b, 1f) giving substit Byla studována kinetika a mechanismus kysele katalyzované hydrolýzy substituovaných 4-alkyl-4-methyl-2-aryl-4,5-dihydro-1,3-oxazol-5-onů na odpovídající 2-alkyl-2-benzoylaminopropanové kyseliny. Taftova korelace rychlostních konstant kysele katalyzované hydrolýzy v závislosti na alkylsubstituci v poloze 4- 1,3-oxazol-5-onového cyklu je nelineární. U Hammettovy korelace dochází v závislosti na rostoucí sterické náročnosti alkylsubstituentu k snižování hodnoty konstanty. U 4-isopropylderivátů je rho = ?0.63 a u t-butylderivátů ?0.32. Protonované 4-isopropyl deriváty jsou nukleofilně atakovány vodou na karbonylovém uhlíku v poloze 5- 1,3-oxazol-5-onového cyklu cca z 70% a t-butylderiváty cca z 60%. Druhou reakční cestou je nukleofilní atak vody na iminový atom uhlíku v poloze 2- 1,3-oxazol-5-onového cyklu. Kinetika aminolýz 4-isopropyl-4-methyl-2-fenyl-1,3-oxazol-5(4H)-onu, 4-isopropyl-2-(4-metoxyfenyl)-4-methyl-1,3-oxazol-5(4H)-onu a 4-isopropyl-4-methyl-2-(4-nitrofenyl)-1,3-oxazol-5(4H)-onu na N-{1, The kinetics and mechanism of the acid-catalysed hydrolysis of substituted 4-alkyl-4-methyl-2-aryt-4,5-dihydro-1, 3-oxazol-5-ones to the corresponding 2-alkyl-2-benzoylaminopropanoic acids were studied. The Taft correlation of rate constants of the acid-catalysed hydrolysis with alkyl substitution at the 4-position of the 1,3-oxazol-5-one ring is non-linear. In the Hammett correlation, the value of rho to decreases with increasing steric demand of the alkyl substituent. With the 4-isopropyl and tert-butyl derivatives, rho = -0.63 and -0.32, respectively. The protonated 4-isopropyl and tert-butyl derivatives undergo nucleophilic attack by water at the carbonyl carbon atom at the 5-position of the 1,3-oxazol-5-one ring to the extents of ca 70% and 60%, respectively. Another reaction path consists in nucleophilic attack by water at the 2-position of the 1,3-oxazol-5-one ring. The reaction kinetics of aminolyses of substituted 4-isopropyl-4-methyl-2-phenyl-1,3-oxazol-5(4H)-ones (1a, 1b, 1f) giving substit
dcterms:title
Steric and electronic substituent effects in hydrolysis and aminolysis of 4-alkyl-4-methyl-2-aryl-4,5-dihydro-1,3-oxazol-5-ones Sterické a elektronické substituční vlivy při hydrolýze a aminolýze 4-alkyl-4-methyl-2-aryl-4,5-dihydro-1,3-oxazol-5-onů Steric and electronic substituent effects in hydrolysis and aminolysis of 4-alkyl-4-methyl-2-aryl-4,5-dihydro-1,3-oxazol-5-ones
skos:prefLabel
Sterické a elektronické substituční vlivy při hydrolýze a aminolýze 4-alkyl-4-methyl-2-aryl-4,5-dihydro-1,3-oxazol-5-onů Steric and electronic substituent effects in hydrolysis and aminolysis of 4-alkyl-4-methyl-2-aryl-4,5-dihydro-1,3-oxazol-5-ones Steric and electronic substituent effects in hydrolysis and aminolysis of 4-alkyl-4-methyl-2-aryl-4,5-dihydro-1,3-oxazol-5-ones
skos:notation
RIV/00216275:25310/05:00003027!RIV08-MSM-25310___
n5:strany
743-750
n5:aktivita
n16:Z
n5:aktivity
Z(MSM0021627501)
n5:cisloPeriodika
8
n5:dodaniDat
n8:2008
n5:domaciTvurceVysledku
n6:1357727 n6:4978684
n5:druhVysledku
n18:J
n5:duvernostUdaju
n15:S
n5:entitaPredkladatele
n11:predkladatel
n5:idSjednocenehoVysledku
544701
n5:idVysledku
RIV/00216275:25310/05:00003027
n5:jazykVysledku
n10:eng
n5:klicovaSlova
hydrolysis; aminolysis; substituent effects; azlactones
n5:klicoveSlovo
n9:aminolysis n9:substituent%20effects n9:azlactones n9:hydrolysis
n5:kodStatuVydavatele
GB - Spojené království Velké Británie a Severního Irska
n5:kontrolniKodProRIV
[8F122C68F14C]
n5:nazevZdroje
Journal of Physical Organic Chemistry
n5:obor
n13:CC
n5:pocetDomacichTvurcuVysledku
2
n5:pocetTvurcuVysledku
4
n5:rokUplatneniVysledku
n8:2005
n5:svazekPeriodika
18
n5:tvurceVysledku
Skála, Pavel Keder, Roman Hanusek, Jiří Sedlák, Miloš
n5:zamer
n17:MSM0021627501
s:issn
0894-3230
s:numberOfPages
8
n12:organizacniJednotka
25310