Phenyl-ring rotational disorder in the two-dimensional hydrogen-bonded structure of the 1:1 proton-transfer salt of the diazo-dye precursor 4-(phenyl-diazenyl)aniline (aniline yellow) with l-tartaric acid

G Smith; U D Wermuth; David James Young

doi:10.1107/S0108270110020597

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Phenyl-ring rotational disorder in the two-dimensional hydrogen-bonded structure of the 1:1 proton-transfer salt of the diazo-dye precursor 4-(phenyl-diazenyl)aniline (aniline yellow) with l-tartaric acid

Journal article

Peer reviewed

Phenyl-ring rotational disorder in the two-dimensional hydrogen-bonded structure of the 1:1 proton-transfer salt of the diazo-dye precursor 4-(phenyl-diazenyl)aniline (aniline yellow) with l-tartaric acid

G Smith, U D Wermuth and David James Young

Acta Crystallographica Section C: Crystal Structure Communications, Vol.66(7), pp.345-348

2010

DOI: https://doi.org/10.1107/S0108270110020597

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Abstract

assembly process

asymmetric unit

bonded sheets

graph set

hydrogen-bonded structures

l-tartaric acids

phenyl rings

proton-transfer compounds

ring centroid

rotational disorder

acids

aniline

azo dyes

carboxylation

hydrogen

negative ions

In the structure of the 1:1 proton-transfer compound from the reaction of l-tartaric acid with the azo-dye precursor aniline yellow [4-(phenyl - diazenyl)aniline], namely 4-(phenyl-di-az-enyl)-anilinium (2R,3R)-3-carb-oxy-2, 3-dihy-droxy-propano-ate, C12H12N3 +.C4H5O6 -, the asymmetric unit contains two independent 4-(phenyl-diazenyl)-anilinium cations and two hydrogen l-tartrate anions. The structure is unusual in that all four phenyl rings of the two cations have identical rotational disorder with equal occupancy of the conformations. The two hydrogen l-tartrate anions form independent but similar chains through head-to-tail carboxyl-carboxyl-ate O - Hâ‹¯O hydrogen bonds [graph set C(7)], which are then extended into a two-dimensional hydrogen-bonded sheet structure through hy-droxy O - Hâ‹¯O hydrogen-bonded links. The anilinium groups of the 4-(phenyl-diazenyl)-anilinium cations are incorporated into the sheets and also provide inter-nal hydrogen-bonded extensions, while their aromatic tails are layered in the structure without significant association except for weak π-π inter-actions [minimum ring centroid separation = 3.844 (3) Ã…]. The hydrogen l-tartrate residues of both anions exhibit the common short intra-molecular hy-droxy-carboxylate O - Hâ‹¯O hydogen bonds. This work provides a solution to the unusual disorder problem inherent in the structure of this salt, as well as giving another example of the utility of the hydrogen tartrate anion in the generation of sheet substructures in mol-ecular assembly processes. © 2010 International Union of Crystallography.

Details

Title: Phenyl-ring rotational disorder in the two-dimensional hydrogen-bonded structure of the 1:1 proton-transfer salt of the diazo-dye precursor 4-(phenyl-diazenyl)aniline (aniline yellow) with l-tartaric acid
Authors: G Smith (Author) - Queensland University of Technology
U D Wermuth (Author) - Queensland University of Technology
David James Young (Author) - Griffith University
Publication details: Acta Crystallographica Section C: Crystal Structure Communications, Vol.66(7), pp.345-348
Publisher: Wiley-Blackwell Publishing Inc.
Date published: 2010
DOI: 10.1107/S0108270110020597
ISSN: 0108-2701
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99450094502621
Output Type: Journal article

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

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