Conformational Study Of (8α,8′β)-bis(substituted Phenyl)-lignano-9,9'-lactones By Means Of Combined Computational, Database Mining, Nmr, And Chemometric Approaches

dc.creatorKiralj R.
dc.creatorFerreira M.M.C.
dc.creatorDonate P.M.
dc.creatorDa Silva R.
dc.creatorAlbuquerque S.
dc.date2007
dc.date2015-06-30T18:49:26Z
dc.date2015-11-26T14:36:58Z
dc.date2015-06-30T18:49:26Z
dc.date2015-11-26T14:36:58Z
dc.date.accessioned2018-03-28T21:41:06Z
dc.date.available2018-03-28T21:41:06Z
dc.identifier
dc.identifierJournal Of Physical Chemistry A. , v. 111, n. 28, p. 6316 - 6333, 2007.
dc.identifier10895639
dc.identifier10.1021/jp066746m
dc.identifierhttp://www.scopus.com/inward/record.url?eid=2-s2.0-34547499035&partnerID=40&md5=99d3568a2836c46e7751771a53ce6bbd
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/104952
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/104952
dc.identifier2-s2.0-34547499035
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1248959
dc.descriptionβ-(3,4-Methylenedioxybenzyl)-γ-butyrolactone (MDBL) and (-)-hinokinin (HK) were obtained by partial synthesis and characterized by 1H NMR and computational methods (conformational analysis, molecular modeling, structural data mining and chemometrics). Three conformers were detected for MDBL and nine were found for HK. The energy differences are around 1 and 2 kcal mol-1 and rotation barriers are less than 3 and 5 kcal mol-1 for MDBL and HK conformers, respectively. The geometries of these conformers, obtained from semiempirical PM3 and density functional theory (DFT) B3LYP 6-3IG** calculations agree satisfactorily with 1H NMR data (vicinal proton-proton coupling constants) and structures retrieved from the Cambridge Structural Database (torsion angles). DFT combined with some variants of the Haasnoot-de Leeuuw-Altona equations gives the best predictions for the coupling constants. The molecular conformation of MDBL, of HK, and of related systems depends not only on intramolecular interactions but also on crystal packing forces and solvent-solute interactions, in particular hydrogen bonds and polar interactions. Hydration favors more stable HK conformers, which can be important for their behavior in chemical and biological systems. © 2007 American Chemical Society.
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dc.relationJournal of Physical Chemistry A
dc.rightsfechado
dc.sourceScopus
dc.titleConformational Study Of (8α,8′β)-bis(substituted Phenyl)-lignano-9,9'-lactones By Means Of Combined Computational, Database Mining, Nmr, And Chemometric Approaches
dc.typeArtículos de revistas


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