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  • Molecular recognition in proton-transfer compounds of brucine with achiral substituted salicylic acid analogues

    Author(s)
    Smith, Graham
    Wermuth, Urs D
    Healy, Peter C
    White, Jonathan M
    Griffith University Author(s)
    Healy, Peter C.
    Wermuth, Urs D.
    Year published
    2006
    Metadata
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    Abstract
    The 1:1 proton-transfer brucinium compounds from the reaction of the alkaloid brucine with 5-nitrosalicylic acid, 3,5-dinitrosalicylic acid, and 5-sulfosalicylic acid, namely anhydrous brucinium 5-nitrosalicylate (1), brucinium 3,5-dinitrosalicylate monohydrate (2), and brucinium 5-sulfosalicylate trihydrate (3) have been prepared and their crystal structures determined by X-ray crystallography. All structures further demonstrate the selectivity of brucine for meta-substituted benzoic acids and comprise three-dimensional hydrogen-bonded framework polymers. Two of the compounds (1 and 3) have the previously described undulating ...
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    The 1:1 proton-transfer brucinium compounds from the reaction of the alkaloid brucine with 5-nitrosalicylic acid, 3,5-dinitrosalicylic acid, and 5-sulfosalicylic acid, namely anhydrous brucinium 5-nitrosalicylate (1), brucinium 3,5-dinitrosalicylate monohydrate (2), and brucinium 5-sulfosalicylate trihydrate (3) have been prepared and their crystal structures determined by X-ray crystallography. All structures further demonstrate the selectivity of brucine for meta-substituted benzoic acids and comprise three-dimensional hydrogen-bonded framework polymers. Two of the compounds (1 and 3) have the previously described undulating brucine sheet host-substructures which incorporate interstitially hydrogen-bonded salicylate anion guest species and additionally in 3 the water molecules of solvation. The structure of 2 differs in having a three-centre brucinium-salicylate anion bidentate N+-H緷O(carboxyl) hydrogen-bonding association linking the species through interstitial associations involving also the water molecules of solvation. A review of the crystallographic structural literature on strychnine and brucine is also given.
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    Journal Title
    Australian Journal of Chemistry
    Volume
    59
    Issue
    5
    DOI
    https://doi.org/10.1071/CH06074
    Subject
    Chemical sciences
    Publication URI
    http://hdl.handle.net/10072/14337
    Collection
    • Journal articles

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