Zigzag hydrogen-bonded sheets in the structure of<i>p</i>-phenylazoaniline hydrochloride

Mahmoudkhani, Amir; Langer, Vratislav

doi:10.1107/s1600536801012971

Cited by 3 publications

(4 citation statements)

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“…For structural data on N-picryl-substituted anilines, see: Forlani et al (1992); Pan et al (2007); Smith et al (2007); Braun et al (2008); . For diazenyl-protonated salts of aniline yellow, see: Mahmoudkhani & Langer (2001); Smith et al ( , 2011.…”

Section: Related Literaturementioning

confidence: 99%

2,4,6-Trinitro-N-[4-(phenyldiazenyl)phenyl]aniline

Smith

Wermuth

2011

Acta Cryst E

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The title compound, C18H12N6O6, was prepared from the reaction of 4-(phenyldiazenyl)aniline (aniline yellow) with picrylsulfonic acid. The dihedral angle formed by the two benzene rings of the diphenyldiazenyl ring system is 6.55 (13)° and that formed by the rings of the picrate–aniline ring system is 48.76 (12)°. The molecule contains an intramolecular aniline–nitro N—H⋯O hydrogen bond.

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Section: Related Literaturementioning

confidence: 99%

2,4,6-Trinitro-N-[4-(phenyldiazenyl)phenyl]aniline

Smith

Wermuth

2011

Acta Cryst E

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“…For the diazo-dye precursor aniline yellow [4-(phenyldiazenyl)aniline], see: O'Neil (2001). For structural data on diazenylprotonated salts of aniline yellow, see: Yatsenko et al (2000); Mahmoudkhani & Langer (2001a); Smith et al (2009). For amine-protonated salts of aniline yellow, see: Mahmoudkhani & Langer (2001b); Smith et al (2008).…”

Section: Related Literaturementioning

confidence: 99%

“…The diazo-dye precursor 4-(phenyldiazenyl)aniline (aniline yellow) (O′Neil, 2001) has been found to react with strong acids to form salts through protonation of the diazenyl group rather than the amine group of the molecule, e.g with the hydrochloride (Yatsenko et al, 2000;Mahmoudkhani & Langer, 2001a), and with 5-sulfosalicylic acid (Smith et al, 2009). With benzenesulfonic acid (Smith et al, 2009), the structure of the dichroic salt showed the 1:1 presence of both the diazenyl-and the amine-protonated forms.…”

Section: S1 Commentmentioning

confidence: 99%

2-(4-Aminophenyl)-1-phenyldiazenium 2,4,6-trinitrophenolate

2011

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In the title salt, C12H12N3 +·C6H2N3O7 −, the diazenyl group of the 4-(phenyldiazenyl)aniline molecule is protonated and forms a hydrogen bond with the phenolate O-atom acceptor of the picrate anion. Structure extension occurs through two symmetrical inter-ion three-centre amine N—H⋯O,O′nitro hydrogen-bonding associations [graph set R 1 2(4)], giving a convoluted two-dimensional network structure.

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“…the 5-sulfosalicylate salt, while in the structure of the unusual dichroic red to red-black salt with benzenesulfonic acid (Smith et al, 2009) both aniline-and diazenylprotonated species co-exist. The distinctive colour allows qualitative recognition of the nature of the salt which, in the case of the hydrochloride, is purple-black with a metallic sheen (Yatsenko et al, 2000;Mahmoudkhani & Langer, 2001a).…”

Section: Commentmentioning

confidence: 99%

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

2010

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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-(phenyldiazenyl)aniline], namely 4-(phenyldiazenyl)anilinium (2R,3R)-3-carboxy-2,3-dihydroxypropanoate, C(12)H(12)N(3)(+) x C(4)H(5)O(6)(-), the asymmetric unit contains two independent 4-(phenyldiazenyl)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-carboxylate O-H...O hydrogen bonds [graph set C(7)], which are then extended into a two-dimensional hydrogen-bonded sheet structure through hydroxy O-H...O hydrogen-bonded links. The anilinium groups of the 4-(phenyldiazenyl)anilinium cations are incorporated into the sheets and also provide internal hydrogen-bonded extensions, while their aromatic tails are layered in the structure without significant association except for weak pi-pi interactions [minimum ring centroid separation = 3.844 (3) A]. The hydrogen L-tartrate residues of both anions exhibit the common short intramolecular hydroxy-carboxylate O-H...O hydrogen 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 molecular assembly processes.

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Zigzag hydrogen-bonded sheets in the structure ofp-phenylazoaniline hydrochloride

Abstract: Key indicatorsSingle-crystal X-ray study T = 297 K Mean '(C±C) = 0.003 A Ê R factor = 0.052 wR factor = 0.150 Data-to-parameter ratio = 11.9For details of how these key indicators were automatically derived from the article, see

Cited by 3 publications

References 1 publication

2,4,6-Trinitro-N-[4-(phenyldiazenyl)phenyl]aniline

2,4,6-Trinitro-N-[4-(phenyldiazenyl)phenyl]aniline

2-(4-Aminophenyl)-1-phenyldiazenium 2,4,6-trinitrophenolate

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

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