Conformation of the galactose ring adopted in solution and in crystalline form as determined by experimental and DFT 1H NMR and single-crystal X-ray analysis

MU Roslund, KD Klika, RL Lehtila, P Tahtinen, R Sillanpaa, Reko Leino

    Tutkimustuotos: LehtiartikkeliArtikkeliTieteellinenvertaisarvioitu

    49 Sitaatiot (Scopus)

    Abstrakti

    The solution-state conformations of various galactose derivatives were determined by comparison of the experimental H-1-H-1 vicinal coupling constants to those calculated using density functional theory (DFT) at the B3LYP/cc-pVTZ//B3LYP/6-31G(d,p) level of theory. The agreement between the experimental and calculated vicinal coupling constants for 1,2:3,4-di-O-isopropylidene- alpha-D-galactopyranose was good, thereby confirming an S-0(2) skew conformation for it and its derivatives on the basis of their similar observed couplings. Single-crystal X-ray analysis of 1,2:3,4-di-O-isopropylidene-6-O-(3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-beta-D-glucopyranoyl)-alpha-D-galacto-pyranose and 1,2,3,4,6-penta-O-acetyl-alpha-D-galactopyranose provided S-0(2) and C-4(1), conformations, respectively, for the galactose ring in the solid state. The solid-state structures proved to be suitable starting structures for further DFT structure refinement or for immediate calculation of the coupling constants.
    AlkuperäiskieliEi tiedossa
    Sivut18–25
    Sivumäärä8
    JulkaisuJournal of Organic Chemistry
    Vuosikerta69
    Numero1
    DOI - pysyväislinkit
    TilaJulkaistu - 2004
    OKM-julkaisutyyppiA1 Julkaistu artikkeli, soviteltu

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