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dc.creatorMarkovic, R
dc.creatorShirazi, A
dc.creatorDzambaski, Z
dc.creatorBaranac-Stojanović, Marija
dc.creatorMinić, Dragica M.
dc.date.accessioned2018-11-22T00:06:41Z
dc.date.available2018-11-22T00:06:41Z
dc.date.issued2004
dc.identifier.issn0894-3230
dc.identifier.urihttp://cherry.chem.bg.ac.rs/handle/123456789/567
dc.description.abstractH-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.publisherJohn Wiley & Sons Ltd, Chichester
dc.rightsrestrictedAccess
dc.sourceJournal of Physical Organic Chemistry
dc.subjectpush-pull alkenesen
dc.subjectZ/E isomerizationen
dc.subjecthydrogen bondingen
dc.subjecttemperature effecten
dc.subjectH-1 NMR spectroscopyen
dc.titleConfigurational isomerization of push-pull thiazoliclinone derivatives controlled by intermolecular and-intramolecular RAHB: H-1 NMR dynamic investigation of concentration and temperature effectsen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractСхирази, A; Марковиц, Р; Баранац-Стојановић, Марија; Миниц, Д; Дзамбаски, З;
dc.citation.volume17
dc.citation.issue2
dc.citation.spage118
dc.citation.epage123
dc.identifier.wos000188820800005
dc.identifier.doi10.1002/poc.700
dc.citation.other17(2): 118-123
dc.citation.rankM23
dc.type.versionpublishedVersionen
dc.identifier.scopus2-s2.0-0442280598
dc.identifier.rcubKon_1566


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