These tools will no longer be maintained as of December 31, 2024. Archived website can be found here. PubMed4Hh GitHub repository can be found here. Contact NLM Customer Service if you have questions.


Pubmed for Handhelds

PUBMED FOR HANDHELDS

Search MEDLINE/PubMed

  • Title: Disordered hydrogen bonding in N-(1-deoxy-beta-D-fructopyranos-1-yl)-N-allylaniline.
    Author: Mossine VV, Barnes CL, Mawhinney TP.
    Journal: Carbohydr Res; 2009 May 12; 344(7):948-51. PubMed ID: 19345935.
    Abstract:
    We report on a (13)C NMR and a single-crystal X-ray diffraction study of N-(1-deoxy-beta-D-fructopyranos-1-yl)-N-allylaniline (D-fructose-N-allylaniline). In solution, an equilibrium of alpha-pyranose, beta-pyranose, alpha-furanose, beta-furanose, and acyclic keto tautomers of the carbohydrate was detected in the following respective proportions: 2.2%, 47.4%, 4.5%, 33.6%, and 12.3%. In the crystalline state, the compound exists exclusively as the beta-pyranose form, in the normal (2)C(5) chair conformation. Bond lengths and valence angles compare well with the average values from a number of beta-fructopyranose derivatives. The structure displays two unusual features for this class of compounds. First, the molecule assumes an eclipsed conformation around the C1-C2 bond, apparently stabilized by an intramolecular O2-H...N hydrogen bond. Second, the O3, O4, and O5 hydroxyl groups are involved in an intermolecular hydrogen bonding, which forms 12-membered homodromic cycles. In the cycles, each determined hydrogen atom site is half occupied, possibly due to the ...H-O...H-O...right harpoon over left harpoon...O-H...O-H... flip-flop type disorder.
    [Abstract] [Full Text] [Related] [New Search]