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Statements

Subject Item
n2:RIV%2F61388955%3A_____%2F08%3A00320339%21RIV09-AV0-61388955
rdf:type
skos:Concept n14:Vysledek
dcterms:description
In the frame of studies of molecules with two redox centers, two isomeric monooximes derived from aryl-alkyl 1,2-diketones were electrochemically investigated. Whereas 1-phenyl-2-oxo-1-oximinopropane is reduced in acidic media according to the mechanism typical for oximes, that means by fou electrons yielding aminoketone, which is further reduced bielectronically under splitting of ammonia, its isomer 1-phenyl-1-oxo-2-oximinopropane is reduced to the stable 1-hydroxy-2-aminoolefine (enol form) and this corresponds to the reduction mechanism of benzil. It is surprising that the unsymmetric molecule behaves like the symmetric one. Basing on the electrochemical data and their correlation with quantum chemical calculations it was possible to explain this phenomenon. In the frame of studies of molecules with two redox centers, two isomeric monooximes derived from aryl-alkyl 1,2-diketones were electrochemically investigated. Whereas 1-phenyl-2-oxo-1-oximinopropane is reduced in acidic media according to the mechanism typical for oximes, that means by fou electrons yielding aminoketone, which is further reduced bielectronically under splitting of ammonia, its isomer 1-phenyl-1-oxo-2-oximinopropane is reduced to the stable 1-hydroxy-2-aminoolefine (enol form) and this corresponds to the reduction mechanism of benzil. It is surprising that the unsymmetric molecule behaves like the symmetric one. Basing on the electrochemical data and their correlation with quantum chemical calculations it was possible to explain this phenomenon. V rámci studia molekul se dvěma redox centry byly studovány dva izomérní mnooximy odvozené od aryl alkyl-1,2-diketonu. Zatímco 1-fenyl-2-oxo-1-oximinopropan se v kyselém prostředí redukuje mechanismem typickým pro oximy, tedy čtyřmi elektrony na aminoketon, který pak v druhém kroku ztrácí reduktivně aminoskupinu, jeho izomér 1-fenyl-1-oxo-2-oximinopropan se redukuje na dále neredukovatelný 1-hydroxy-2-aminoolefin (enol forma), což je analogické redukci benzilu. Zde je zvláště překvapivé, že nesymetrická molekula se redukuje mechanismem typickým pro molekuly symetrické. Na základě elektrochemických dat a jejich korelace s kvantovými výpočty se podařilo důvod tohoto jevu vysvětlit.
dcterms:title
Intramolecular electronic interactions in two types of dicarbonyl compounds and their derivatives – an electrochemical and quantum chemical study Intramolecular electronic interactions in two types of dicarbonyl compounds and their derivatives – an electrochemical and quantum chemical study Intramolekulární elektronová interakce dvou typů dikarbonylových slouočenin a jejich derivátů – elektrochemická a kvantově chemická studie
skos:prefLabel
Intramolecular electronic interactions in two types of dicarbonyl compounds and their derivatives – an electrochemical and quantum chemical study Intramolecular electronic interactions in two types of dicarbonyl compounds and their derivatives – an electrochemical and quantum chemical study Intramolekulární elektronová interakce dvou typů dikarbonylových slouočenin a jejich derivátů – elektrochemická a kvantově chemická studie
skos:notation
RIV/61388955:_____/08:00320339!RIV09-AV0-61388955
n3:aktivita
n5:Z n5:P
n3:aktivity
P(1P05ME785), Z(AV0Z40400503)
n3:dodaniDat
n6:2009
n3:domaciTvurceVysledku
n15:6701434 n15:4441613
n3:druhVysledku
n19:D
n3:duvernostUdaju
n10:S
n3:entitaPredkladatele
n18:predkladatel
n3:idSjednocenehoVysledku
373081
n3:idVysledku
RIV/61388955:_____/08:00320339
n3:jazykVysledku
n17:eng
n3:klicovaSlova
intramolecular electronic interaction; dicarbonyl compounds; electrochemistry
n3:klicoveSlovo
n8:dicarbonyl%20compounds n8:intramolecular%20electronic%20interaction n8:electrochemistry
n3:kontrolniKodProRIV
[8FDAE974FD1F]
n3:mistoKonaniAkce
Prague
n3:mistoVydani
Olomouc
n3:nazevZdroje
Chemické listy
n3:obor
n11:CG
n3:pocetDomacichTvurcuVysledku
2
n3:pocetTvurcuVysledku
4
n3:projekt
n13:1P05ME785
n3:rokUplatneniVysledku
n6:2008
n3:tvurceVysledku
Zuman, P. Celik, H. Ludvík, Jiří Jirkovský, Jaromír
n3:typAkce
n12:WRD
n3:zahajeniAkce
2008-06-16+02:00
n3:zamer
n20:AV0Z40400503
s:issn
0009-2770
s:numberOfPages
2
n16:hasPublisher
Česká společnost chemická