About: Solution and Solid-State Effects on NMR Chemical Shifts in Sesquiterpene Lactones: NMR, X-ray, and Theoretical Methods

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Description	Selected guaianolide type sesquiterpene lactones were studied combining solution and solid-state NMR spectroscopy with theoretical calculations of the chemical shifts in both environments and with the X-ray data. The experimental H-1 and C-13 chemical shifts in solution were successfully reproduced by theoretical calculations (with the GIAO method and DFT B3LYP 6-31++G) after geometry optimization (DFT B3LYP 6-31 G) in vacuum. The GIPAW method was used for calculations of solid-state C-13 chemical shifts. The studied cases involved two polymorphs of helenalin, two pseudopolymorphs of 6 alpha-hydroxydihydro-aromaticin and two cases of multiple asymmetric units in crystals: one in which the symmetry independent molecules were connected by a series of hydrogen bonds (geigerinin) and the other in which the symmetry independent molecules, deprived of any specific intermolecular interactions, differed in the conformation of the side chain (badkhysin). Geometrically different molecules present in the crystal lattices could, be easily distinguished in the solid-state NMR spectra. Moreover, the experimental differences in the C-13 chemical shifts corresponding to nuclei in different polymorphs or in geometrically different molecules were nicely reproduced with the GIPAW calculations. Selected guaianolide type sesquiterpene lactones were studied combining solution and solid-state NMR spectroscopy with theoretical calculations of the chemical shifts in both environments and with the X-ray data. The experimental H-1 and C-13 chemical shifts in solution were successfully reproduced by theoretical calculations (with the GIAO method and DFT B3LYP 6-31++G) after geometry optimization (DFT B3LYP 6-31 G) in vacuum. The GIPAW method was used for calculations of solid-state C-13 chemical shifts. The studied cases involved two polymorphs of helenalin, two pseudopolymorphs of 6 alpha-hydroxydihydro-aromaticin and two cases of multiple asymmetric units in crystals: one in which the symmetry independent molecules were connected by a series of hydrogen bonds (geigerinin) and the other in which the symmetry independent molecules, deprived of any specific intermolecular interactions, differed in the conformation of the side chain (badkhysin). Geometrically different molecules present in the crystal lattices could, be easily distinguished in the solid-state NMR spectra. Moreover, the experimental differences in the C-13 chemical shifts corresponding to nuclei in different polymorphs or in geometrically different molecules were nicely reproduced with the GIPAW calculations. (en)
Title	Solution and Solid-State Effects on NMR Chemical Shifts in Sesquiterpene Lactones: NMR, X-ray, and Theoretical Methods Solution and Solid-State Effects on NMR Chemical Shifts in Sesquiterpene Lactones: NMR, X-ray, and Theoretical Methods (en)
skos:prefLabel	Solution and Solid-State Effects on NMR Chemical Shifts in Sesquiterpene Lactones: NMR, X-ray, and Theoretical Methods Solution and Solid-State Effects on NMR Chemical Shifts in Sesquiterpene Lactones: NMR, X-ray, and Theoretical Methods (en)
skos:notation	RIV/61388963:_____/12:00375520!RIV12-AV0-61388963
http://linked.open...avai/riv/aktivita	P Z
http://linked.open...avai/riv/aktivity	P(GA203/09/1919), P(KJB400550903), Z(AV0Z40550506)
http://linked.open...iv/cisloPeriodika	1
http://linked.open...vai/riv/dodaniDat	2012
http://linked.open...aciTvurceVysledku	Buděšínský, Miloš Dračínský, Martin
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	169134
http://linked.open...ai/riv/idVysledku	RIV/61388963:_____/12:00375520
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	crystal-structures spectroscopy; crystallography; quantum; pseudopotentials (en)
http://linked.open.../riv/klicoveSlovo	quantum crystallography pseudopotentials crystal-structures spectroscopy
http://linked.open...odStatuVydavatele	US - Spojené státy americké
http://linked.open...ontrolniKodProRIV	[EF0CC99719B2]
http://linked.open...i/riv/nazevZdroje	Journal of Physical Chemistry A
http://linked.open...in/vavai/riv/obor	CF
http://linked.open...ichTvurcuVysledku	2 (xsd:int)
http://linked.open...cetTvurcuVysledku	4 (xsd:int)
http://linked.open...vavai/riv/projekt	Development of methods for configuration determination at chiral sulfur, nitrogen or phosphorus atom using NMR spectroscopy and ab initio calculations Study of isotopic exchange of hydrogen in the position 5 of pyrimidine derivatives and synthesis of pyrimidines with biological activity labeled with tritium.
http://linked.open...UplatneniVysledku	2012
http://linked.open...v/svazekPeriodika	116
http://linked.open...iv/tvurceVysledku	Buděšínský, Miloš Dračínský, Martin Rychlewska, U. Warzajtis, B.
http://linked.open...ain/vavai/riv/wos	000298978000072
http://linked.open...n/vavai/riv/zamer	Regulace biologických procesů: Chemické modulátory vybraných systémů významných pro medicínu a zemědělství
issn	1089-5639
number of pages	9 (xsd:int)
http://bibframe.org/vocab/doi	10.1021/jp209408b

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