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

G Smith; U D Wermuth; David James Young; J M White

doi:10.1107/S0108270108001595

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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

Journal article

Peer reviewed

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

G Smith, U D Wermuth, David James Young and J M White

Acta Crystallographica Section C: Crystal Structure Communications, Vol.64(3), pp.123-127

2008

DOI: https://doi.org/10.1107/S0108270108001595

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Abstract

rotational disorders

sheet structures

crystal defects

hydrogen bonds

isomers

nitrogen compounds

organic acids

proton transfer

rotation

The structures of the anhydrous 1:1 proton-transfer compounds of the dye precursor aniline yellow [4-(phenyl-diazenyl)-aniline], namely isomeric 4-(phenyl-diazenyl)-anilin-ium 2-carb-oxy-6-nitro-benzoate, C12H12N3 +.C8H4NO6 -, (I), and 4-(phenyl-diazenyl)-anilinium 2-carb-oxy-4-nitro-benzoate, C12H12N3 +.C8H4NO6 -, (II), and 4-(phenyl-diazenyl)-anilinium 3-carb-oxy-5-nitro-benzoate monohydrate, C12H12N3 +.C8H4-NO6 -.H2O, (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-carboxyl-ate hydrogen-bond inter-actions [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-(phenyl-diazenyl)-anilinium cations into the substructures, including, in the cases of (I) and (II), infinite H - N - H to carboxyl-ate O - C - O group inter-actions [graph set C(6)], and in the case of (III), bridging through the water mol-ecule of solvation. The peripheral alternating aromatic ring residues of both cations and anions give only weakly π-inter-active step features which lie between the sheets. © 2008 International Union of Crystallography.

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Title: The 1:1 proton-transfer compounds of 4-(phenyldiazenyl)aniline (aniline yellow) with 3-nitrophthalic, 4-nitrophthalic and 5-nitroisophthalic acids
Authors: G Smith (Author) - Queensland University of Technology
U D Wermuth (Author) - Queensland University of Technology
David James Young (Author) - Griffith University
J M White (Author) - University of Melbourne
Publication details: Acta Crystallographica Section C: Crystal Structure Communications, Vol.64(3), pp.123-127
Publisher: Wiley-Blackwell Publishing Inc.
Date published: 2008
DOI: 10.1107/S0108270108001595
ISSN: 0108-2701
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99450079202621
Output Type: Journal article

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Collaboration types: Domestic collaboration
Web Of Science research areas: Chemistry, Multidisciplinary; Crystallography

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