About: Influence of Cu(II) Ions on the Mechanism of the Ring Transformation of S-(2-Oxotetrahydrofuran-3-yl)-N-(4-methoxyphenyl)isothiouronium Bromide

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About: Influence of Cu(II) Ions on the Mechanism of the Ring Transformation of S-(2-Oxotetrahydrofuran-3-yl)-N-(4-methoxyphenyl)isothiouronium Bromide Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	The effect of additional Cu(II) ions on the rate of transformation of S-(2-oxotetrahydrofuran-3-yl)-N-(4-methoxyphenyl)isothiouronium bromide (1) into 5-(2-hydroxyethyl)-2-[(4-methoxyphenyl)imino]-1,3-thiazolidin-4-one (2) has been studied in aqueous buffer solutions. The reaction acceleration in acetate buffers is caused by the formation of a relatively weakly bonded complex (Kc = 600 L center dot mol1) of substrate with copper(II) acetate in which the Cu(II) ion acts as a Lewis acid coordinating the carbonyl oxygen and facilitating the intramolecular attack, leading to the formation of intermediate T +/-. The formation of the complex of copper(II) acetate with free isothiourea in the fast preequilibrium (Kc) is followed by the rate-limiting transformation (kCu) of this complex. At the high concentrations of the acetate anions, the reaction is retarded by the competitive reaction of these ions with copper(II) acetate to give an unreactive complex [Cu(OAc)4]2. The influence of Cu(II) ions on the stability of reaction intermediates and the leaving group ability of the alkoxide-leaving group compared to the Cu(II)-uncatalyzed reaction is also discussed. The effect of additional Cu(II) ions on the rate of transformation of S-(2-oxotetrahydrofuran-3-yl)-N-(4-methoxyphenyl)isothiouronium bromide (1) into 5-(2-hydroxyethyl)-2-[(4-methoxyphenyl)imino]-1,3-thiazolidin-4-one (2) has been studied in aqueous buffer solutions. The reaction acceleration in acetate buffers is caused by the formation of a relatively weakly bonded complex (Kc = 600 L center dot mol1) of substrate with copper(II) acetate in which the Cu(II) ion acts as a Lewis acid coordinating the carbonyl oxygen and facilitating the intramolecular attack, leading to the formation of intermediate T +/-. The formation of the complex of copper(II) acetate with free isothiourea in the fast preequilibrium (Kc) is followed by the rate-limiting transformation (kCu) of this complex. At the high concentrations of the acetate anions, the reaction is retarded by the competitive reaction of these ions with copper(II) acetate to give an unreactive complex [Cu(OAc)4]2. The influence of Cu(II) ions on the stability of reaction intermediates and the leaving group ability of the alkoxide-leaving group compared to the Cu(II)-uncatalyzed reaction is also discussed. (en)
Title	Influence of Cu(II) Ions on the Mechanism of the Ring Transformation of S-(2-Oxotetrahydrofuran-3-yl)-N-(4-methoxyphenyl)isothiouronium Bromide Influence of Cu(II) Ions on the Mechanism of the Ring Transformation of S-(2-Oxotetrahydrofuran-3-yl)-N-(4-methoxyphenyl)isothiouronium Bromide (en)
skos:prefLabel	Influence of Cu(II) Ions on the Mechanism of the Ring Transformation of S-(2-Oxotetrahydrofuran-3-yl)-N-(4-methoxyphenyl)isothiouronium Bromide Influence of Cu(II) Ions on the Mechanism of the Ring Transformation of S-(2-Oxotetrahydrofuran-3-yl)-N-(4-methoxyphenyl)isothiouronium Bromide (en)
skos:notation	RIV/00216275:25310/13:39896103!RIV14-MSM-25310___
http://linked.open...avai/riv/aktivita	P
http://linked.open...avai/riv/aktivity	P(EE2.3.30.0021)
http://linked.open...iv/cisloPeriodika	4
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Sedlák, Miloš Hanusek, Jiří Váňa, Jiří
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Pardubice / Fakulta chemicko-technologická
http://linked.open...dnocenehoVysledku	79715
http://linked.open...ai/riv/idVysledku	RIV/00216275:25310/13:39896103
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	models; ligands; kinetics; methanolysis; esters; hydrolysis; acid-catalysis; catalyzed reactions; copper(ii) complexes; metal-ions (en)
http://linked.open.../riv/klicoveSlovo	methanolysis esters kinetics ligands models acid-catalysis catalyzed reactions copper(ii) complexes hydrolysis metal-ions
http://linked.open...odStatuVydavatele	US - Spojené státy americké
http://linked.open...ontrolniKodProRIV	[EE76EBDBA74B]
http://linked.open...i/riv/nazevZdroje	INTERNATIONAL JOURNAL OF CHEMICAL KINETICS
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	3 (xsd:int)
http://linked.open...cetTvurcuVysledku	3 (xsd:int)
http://linked.open...vavai/riv/projekt	Strenthening of Research and Development Teams at the University of Pardubice
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	45
http://linked.open...iv/tvurceVysledku	Váňa, Jiří Sedlák, Miloš Hanusek, Jiří
http://linked.open...ain/vavai/riv/wos	000315352700005
issn	0538-8066
number of pages	8 (xsd:int)
http://bibframe.org/vocab/doi	10.1002/kin.20761
http://localhost/t...ganizacniJednotka	25310

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