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Conformation of eight-membered benzoannulated lactams by combined NMR and DFT studies

Conformation of eight-membered benzoannulated lactams ...

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dc.contributor.author Witosińska, Agnieszka pl
dc.contributor.author Musielak, Bogdan [SAP14008194] pl
dc.contributor.author Serda, Paweł [SAP11010084] pl
dc.contributor.author Owińska, Maria pl
dc.contributor.author Rys, Barbara [SAP11006643] pl
dc.date.accessioned 2015-03-12T07:44:27Z
dc.date.available 2015-03-12T07:44:27Z
dc.date.issued 2012 pl
dc.identifier.issn 0022-3263 pl
dc.identifier.uri http://ruj.uj.edu.pl/xmlui/handle/item/3743
dc.language eng pl
dc.title Conformation of eight-membered benzoannulated lactams by combined NMR and DFT studies pl
dc.type JournalArticle pl
dc.description.physical 9784-9794 pl
dc.abstract.en The title compounds were synthesized, and their structure and conformational behavior in solution (NMR and DFT), in the gas phase (DFT), and, for some of them, in the solid state (X-ray) were investigated. The variable -temperature NMR spectra were employed to determine the conformational equilibria and the activation energy of the conformational changes of the eight-membered ring. The coalescence e ff ects are assigned to racemization of the chiral ground- state conformation with a ring inversion barrier in the range of 38 − 100 kJ mol − 1 depending on the relative setting of the two strong conformational constraints: benzoannulation and the amide function. The second conformational process, interconversion between two di ff erent conformers, in the molecules of benzo[ c ]azocin-3-one, benzo[ d ]azocin-2-one, and benzo[ d ]azocin-4-one was observed. The natures of the conformers observed in solution were elucidated by analysis of experimental and calculated NMR data. The present results are discussed in conjunction with previous experimental and theoretical data on ( Z , Z )-cyclooctadienes and their benzo analogues. pl
dc.description.volume 77 pl
dc.description.number 21 pl
dc.identifier.doi 10.1021/jo301859h pl
dc.identifier.eissn 1520-6904 pl
dc.title.journal The Journal of Organic Chemistry pl
dc.language.container eng pl
dc.affiliation Wydział Chemii : Zakład Krystalochemii i Krystalofizyki pl
dc.affiliation Wydział Chemii : Zakład Chemii Organicznej pl
dc.subtype Article pl
dc.rights.original bez licencji pl
.pointsMNiSW [2012 A]: 35


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