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

Content Provider	Semantic Scholar
Author	Smith, Graham Wermuth, Urs D. Young, David James White, Jonathan M.
Copyright Year	2008
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, C(12)H(12)N(3)(+) x C(8)H(4)NO(6)(-), (I), and 4-(phenyldiazenyl)anilinium 2-carboxy-4-nitrobenzoate, C(12)H(12)N(3)(+) x C(8)H(4)NO(6)(-), (II), and 4-(phenyldiazenyl)anilinium 3-carboxy-5-nitrobenzoate monohydrate, C(12)H(12)N(3)(+) x C(8)H(4)NO(6)(-) x H(2)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.
Starting Page	326
Ending Page	340
Page Count	15
File Format	PDF HTM / HTML
DOI	10.1107/S0108270108001595
Alternate Webpage(s)	https://journals.iucr.org/c/issues/2008/03/00/gz3114/gz3114.pdf
PubMed reference number	18322335
Alternate Webpage(s)	https://doi.org/10.1107/S0108270108001595
Journal	Medline
Volume Number	64
Part	3
Journal	Acta crystallographica. Section C, Crystal structure communications
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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