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  • The 1:1 proton-transfer compounds of 4-(phenyldiazenyl)aniline (aniline yellow) with 3-nitrophthalic, 4-nitrophthalic and 5-nitroisophthalic acids

    Author(s)
    Smith, Graham
    Wermuth, Urs D
    Young, David J
    White, Jonathan M
    Griffith University Author(s)
    Wermuth, Urs D.
    Young, David
    Year published
    2008
    Metadata
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    Abstract
    The structures of the anhydrous 1:1 proton-transfer compounds of the dye precursor aniline yellow [4-(phenyldiazenyl)aniline], namely isomeric 4-(phenyldiazenyl)anilinium 2-carboxy-6-nitrobenzoate, C12H12N3+烸H4NO6-, (I), and 4-(phenyldiazenyl)anilinium 2-carboxy-4-nitrobenzoate, C12H12N3+烸H4NO6-, (II), and 4-(phenyldiazenyl)anilinium 3-carboxy-5-nitrobenzoate monohydrate, C12H12N3+烸H4NO6-爲O, (III), have been determined at 130 K. In (I) the cation has longitudinal rotational disorder. All three compounds have substructures comprising backbones formed through strong head-to-tail carboxyl-carboxylate hydrogen-bond interactions ...
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    The structures of the anhydrous 1:1 proton-transfer compounds of the dye precursor aniline yellow [4-(phenyldiazenyl)aniline], namely isomeric 4-(phenyldiazenyl)anilinium 2-carboxy-6-nitrobenzoate, C12H12N3+烸H4NO6-, (I), and 4-(phenyldiazenyl)anilinium 2-carboxy-4-nitrobenzoate, C12H12N3+烸H4NO6-, (II), and 4-(phenyldiazenyl)anilinium 3-carboxy-5-nitrobenzoate monohydrate, C12H12N3+烸H4NO6-爲O, (III), have been determined at 130 K. In (I) the cation has longitudinal rotational disorder. All three compounds have substructures comprising backbones formed through strong head-to-tail carboxyl-carboxylate hydrogen-bond interactions [graph set C(7) in (I) and (II), and C(8) in (III)]. Two-dimensional sheet structures are formed in all three compounds by the incorporation of the 4-(phenyldiazenyl)anilinium cations into the substructures, including, in the cases of (I) and (II), infinite H-N-H to carboxylate O-C-O group interactions [graph set C(6)], and in the case of (III), bridging through the water molecule of solvation. The peripheral alternating aromatic ring residues of both cations and anions give only weakly [pi]-interactive step features which lie between the sheets.
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    Journal Title
    Acta Crystallographica Section C: Crystal Structure Communications
    Volume
    C64
    Issue
    3
    DOI
    https://doi.org/10.1107/S0108270108001595
    Subject
    Inorganic chemistry
    Physical chemistry
    Other chemical sciences
    Publication URI
    http://hdl.handle.net/10072/26743
    Collection
    • Journal articles

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