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

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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
Author Smith, Graham; Wermuth, Urs; Young, David; White, Jonathan M.
Journal Name Acta Crystallographica Section C: Crystal Structure Communications
Year Published 2008
Place of publication Denmark
Publisher Wiley-Blackwell
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+·C8H4NO6-, (I), and 4-(phenyldiazenyl)anilinium 2-carboxy-4-nitrobenzoate, C12H12N3+·C8H4NO6-, (II), and 4-(phenyldiazenyl)anilinium 3-carboxy-5-nitrobenzoate monohydrate, C12H12N3+·C8H4NO6-·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-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.
Peer Reviewed Yes
Published Yes
Alternative URI http://onlinelibrary.wiley.com/doi/10.1107/S0108270108001595/abstract
Volume C64
Issue Number 3
Page from o123
Page to o127
ISSN 0108-2701
Date Accessioned 2009-04-16
Date Available 2011-06-09T22:41:18Z
Language en_AU
Faculty Faculty of Science, Environment, Engineering and Technology
Subject PRE2009-Structural Chemistry
URI http://hdl.handle.net/10072/26743
Publication Type Journal Articles (Refereed Article)
Publication Type Code c1

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