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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
Journal article   Peer reviewed

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, U D Wermuth, David James Young and J M White
Acta Crystallographica Section C: Crystal Structure Communications, Vol.65(10), pp.543-548
2009
DOI: https://doi.org/10.1107/S0108270109036622
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https://doi.org/10.1107/S0108270109036622View
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Abstract

5-sulfosalicylic acid asymmetric unit benzoic acid homodimers hydrogen bondings one-dimensional chains protonated red-black ribbon structures sulfonic acid three-dimensional frameworks aniline atoms benzene binding sites complexation
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 than the aniline group of aniline yellow is protonated, and this group subsequently takes part in a primary hydrogen-bonding inter-action with a sulfonate O-atom acceptor, producing overall a three-dimensional framework structure. A feature of the hydrogen bonding in (I) is a peripheral edge-on cation-anion association also involving aromatic C - H⋯O hydrogen bonds, giving a conjoint R 1 2(6)R 1 2(7)R 2 1(4) motif. In the dichroic crystals of (II), one of the two aniline yellow species in the asymmetric unit is diazenyl-group protonated, while in the other the aniline group is protonated. Both of these groups form hydrogen bonds with sulfonate O-atom acceptors and these, together with other associations, give a one-dimensional chain structure. In compound (III), rather than proton transfer, there is preferential formation of a classic R 2 2(8) cyclic head-to-head hydrogen-bonded car-box-ylic acid homodimer between the two 3,5-dinitro-benzoic acid mol-ecules, which, in association with the aniline yellow mol-ecule that is disordered across a crystallographic inversion centre, results in an overall two-dimensional ribbon structure. This work has shown the correlation between structure and observed colour in crystalline aniline yellow compounds, illustrated graphically in the dichroic benzene-sulfonate compound. © 2009 International Union of Crystallography.

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