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Configurational isomerization of push-pull thiazoliclinone derivatives controlled by intermolecular and-intramolecular RAHB: H-1 NMR dynamic investigation of concentration and temperature effects
dc.creator | Marković, R. | |
dc.creator | Shirazi, A | |
dc.creator | Džambaski, Z. | |
dc.creator | Baranac-Stojanović, Marija | |
dc.creator | Minić, Dragica M. | |
dc.date.accessioned | 2018-11-22T00:06:41Z | |
dc.date.available | 2018-11-22T00:06:41Z | |
dc.date.issued | 2004 | |
dc.identifier.issn | 0894-3230 | |
dc.identifier.uri | https://cherry.chem.bg.ac.rs/handle/123456789/567 | |
dc.description.abstract | H-1 NMR spectroscopy was used to investigate hydrogen bonding in the structurally related (Z)- and (E)-5-substituted-2-alkylidene-4-oxothiazolidines in polar and apolar solvents. The equilibrated mixtures of these typical push-pull alkenes consist of the intramolecularly H-bonded E-isomer and intermolecularly H-bonded Z-isomer in varying proportions which depend on the solvent polarity. For a representative of the series, (E)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-1-phenylethanone (1), the lack of a concentration and temperature dependence of the large chemical NH shift (delta 12.06ppm) in CDCl3 indicates strong intramolecular resonance-assisted hydrogen-bond formation (RAHB). The upfield chemical shifts of the NH proton of the (Z)-1 isomer as a function of temperature increase and the large 1H NMR Deltadelta/DeltaT value (-11.82ppbdegreesC(-1), Z/E=60:40, or -10.33ppbdegreesC(-1), Z/E = 20: 80) in CDCl3 are explained in terms of a decrease in intermolecular H-bonding resulting in a greater amount of free or unassociated Z-isomer. Copyright (C) 2004 John Wiley Sons, Ltd. | en |
dc.publisher | John Wiley & Sons Ltd, Chichester | |
dc.rights | restrictedAccess | |
dc.source | Journal of Physical Organic Chemistry | |
dc.subject | push-pull alkenes | en |
dc.subject | Z/E isomerization | en |
dc.subject | hydrogen bonding | en |
dc.subject | temperature effect | en |
dc.subject | H-1 NMR spectroscopy | en |
dc.title | Configurational isomerization of push-pull thiazoliclinone derivatives controlled by intermolecular and-intramolecular RAHB: H-1 NMR dynamic investigation of concentration and temperature effects | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Схирази, A; Марковиц, Р; Баранац-Стојановић, Марија; Миниц, Д; Дзамбаски, З; | |
dc.citation.volume | 17 | |
dc.citation.issue | 2 | |
dc.citation.spage | 118 | |
dc.citation.epage | 123 | |
dc.identifier.wos | 000188820800005 | |
dc.identifier.doi | 10.1002/poc.700 | |
dc.citation.other | 17(2): 118-123 | |
dc.citation.rank | M23 | |
dc.type.version | publishedVersion | en |
dc.identifier.scopus | 2-s2.0-0442280598 |