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  • Structural studies on sulfonylbicyclo[n.2.0]alkan-1-ols

    Author(s)
    Healy, PC
    Loughlin, WA
    McCleary, MA
    Pierens, GK
    Rowen, CC
    Griffith University Author(s)
    Healy, Peter C.
    Loughlin, Wendy A.
    Year published
    2002
    Metadata
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    Abstract
    The structures of a series of sulfonylbicyclo[n.2.0]alkan-1-ols (n = 3-6) 1-6 were determined by single-crystal x-ray diffraction. A survey of the Cambridge Structural Database and Monte Carlo conformational searches using MacroModel were performed. Compounds 1, 3 and 4 show intramolecular hydrogen bonding. Compound 2 is stabilized by three-centered bifurcated intra- and intermolecular hydrogen bonds between the hydroxyl proton and the sulfone oxygens. Compounds 5 and 6 are stabilized by intermolecular hydrogen bonds formed between the trans 1-hydroxy and sulfonyl moieties. In compounds 1-6, the degree of cyclotorsion of the ...
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    The structures of a series of sulfonylbicyclo[n.2.0]alkan-1-ols (n = 3-6) 1-6 were determined by single-crystal x-ray diffraction. A survey of the Cambridge Structural Database and Monte Carlo conformational searches using MacroModel were performed. Compounds 1, 3 and 4 show intramolecular hydrogen bonding. Compound 2 is stabilized by three-centered bifurcated intra- and intermolecular hydrogen bonds between the hydroxyl proton and the sulfone oxygens. Compounds 5 and 6 are stabilized by intermolecular hydrogen bonds formed between the trans 1-hydroxy and sulfonyl moieties. In compounds 1-6, the degree of cyclotorsion of the four- five-, six-, seven- and eight-membered rings adjacent to the bond between the bridgehead atoms C1 and C4 is reflected in the magnitude about the exterior angles about C1 (C2 - C1 - Cx) and C4 (C3 - C4 - C5). The six-membered ring systems of 2, 5 and 6 showed noteworthy increases in the C5 - C4 - C1 - Cx and C3 - C4 - C1 - C2 torsion angles, and this was attributed to the conformational constraints of the pseudo-chair conformation of the six-membered ring. Similar conformational structure effects were observed in the modeled structures 1a-6a to those observed for the x-ray structures 1-6.
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    Journal Title
    Journal of Physical Organic Chemistry
    Volume
    15
    Publisher URI
    https://onlinelibrary.wiley.com/doi/10.1002/poc.542
    DOI
    https://doi.org/10.1002/poc.542
    Copyright Statement
    © 2002 John Wiley & Sons, Ltd. Self-archiving of the author-manuscript version is not yet supported by this publisher. Please refer to the journal link for access to the definitive, published version or contact the author for more information.
    Subject
    Organic chemistry
    Physical chemistry
    Theoretical and computational chemistry
    Publication URI
    http://hdl.handle.net/10072/7030
    Collection
    • Journal articles

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