Journal article
Proton transfer versus nontransfer in compounds of the diazo-dye precursor 4-(phenyl-diazenyl)aniline (aniline yellow) with strong organic acids: The 5-sulfosalicylate and the dichroic benzene-sulfonate salts, and the 1:2 adduct with 3,5-dinitro-benzoic acid
G Smith, UD Wermuth, DJ Young, JM White
Acta Crystallographica Section C Crystal Structure Communications | WILEY-BLACKWELL | Published : 2009
Abstract
The structures of two 1:1 proton-transfer red-black dye compounds formed by reaction of aniline yellow [4-(phenyl-diazenyl)aniline] with 5-sulfosalicylic acid and benzene-sulfonic acid, and a 1:2 nontransfer adduct compound with 3,5-dinitro-benzoic acid have been determined at either 130 or 200 K. The compounds are 2-(4-aminophenyl)-1-phenylhydra-zin-1-ium 3-carboxy-4- hydroxybenzenesulfonate methanol solvate, C12H12N 3 +·C7H5O6S -·CH3OH, (I), 2-(4-aminophenyl)-1-phenylhydrazin-1- ium 4-(phenyldiazenyl)anilinium bis(benzenesulfonate), 2C12H 12N3 +·2C6H5O 3S-, (II), and 4-(phenyl-diazenyl)aniline-3,5-dinitro- benzoic acid (1/2), C12H11N3·2C 7H4N2O6, (III). In compound (I), the diazenyl rather..
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Funding Acknowledgements
The authors acknowledge financial support from the Australian Research Council, the School of Physical and Chemical Sciences, Queensland University of Technology, the School of Biomolecular and Physical Sciences, Griffith University, and the School of Chemistry, University of Melbourne.