1-[(<i>E</i>)-2-(5-<i>tert</i>-Butyl-2-hydroxyphenyl)diazen-1-yl]naphthalen-2-ol

Bougueria, Hassiba; Mili, Ali; Benosmane, Ali; Bouchoul, Abd el kader; Bouaoud, Salah-Eddine

doi:10.1107/s1600536814001731

Cited by 5 publications

(3 citation statements)

References 9 publications

(15 reference statements)

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“…1); this is common when there is a OH group in the ortho-position corresponding to the azo group. Bond lengths and angles are within normal ranges and are comparable to those observed in related structures (Bougueria et al, 2014;Chetioui et al, 2013a). The conformational differences between molecules A and B are highlighted in an overlay diagram shown in Fig.…”

Section: Structural Commentarysupporting

confidence: 79%

Crystal structure and Hirshfeld surface analysis of 1-[(E)-2-(5-chloro-2-hydroxyphenyl)hydrazin-1-ylidene]naphthalen-2(1H)-one

Bougueria¹,

Chetioui²,

Bensegueni³

et al. 2021

Acta Cryst E

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The title compound, C16H11ClN2O2, was obtained by diazotization of 2-amino-4-chlorophenol followed by a coupling reaction with β-naphthol. There are two molecules (A and B) in the asymmetric unit. The crystal structure features only one type of intermolecular interaction, that is strong hydrogen bonds involving the hydroxyl group. The naphthol and phenol fragments attached to the C=N—N— moiety exhibit an s-trans conformation. In addition, those fragments are almost coplanar, subtending a dihedral angle of 13.11 (2)° in molecule A and 10.35 (2)° in molecule B. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (32.1%), C...H/H...C (23.1%), Cl...H/H...Cl (15.2%), O...H/H...O (12.8%) and C...C (9%) contacts.

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Section: Structural Commentarysupporting

confidence: 79%

Crystal structure and Hirshfeld surface analysis of 1-[(E)-2-(5-chloro-2-hydroxyphenyl)hydrazin-1-ylidene]naphthalen-2(1H)-one

Bougueria¹,

Chetioui²,

Bensegueni³

et al. 2021

Acta Cryst E

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“…In the case of 1-phenylazo-2-naphthol derivatives, a strong hydrogen bond enhanced by resonance is established, inducing the azo (OH) ! hydrazo (NH) tautomeric displacement (Benosmane et al, 2015;Bougueria et al, 2014). This is directly connected with the presence of at least one protic donor group in conjugation to the azo bridge (2-naphthol) (Antonov, 2016).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 1-[(E)-2-(3-nitrophenyl)diazen-1-yl]naphthalen-2-ol

et al. 2023

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The title compound, C16H11N3O3, belongs to the family of azo dyes. In the light of a single-crystal X-ray study, it is evident that of the tautomeric forms (azo–hydrazone), the hydrazone form is the predominant form in the solid state, namely, (1E)-1-[2-(3-nitrophenyl)hydrazin-1-ylidene]-1,2-dihydronaphthalen-2-one. The naphthol and benzene fragments attached to the –N=N– moiety adopt the s-trans conformation. Furthermore, the molecules are nearly coplanar, subtending a dihedral angle of 2.63 (5)°. An intramolecular N—H...O hydrogen bond occurs. There are only two types of intermolecular interactions in the crystal structure: strong hydrogen-bonding C—H...O interactions and π–π stacking interactions. The importance of C—H...O interactions in the molecular packing is reflected by the relatively high contributions (28.5%) made by O...H/H...O contacts to the Hirshfeld surface.

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“…There are three published examples of molecules containing the 2,2 0 -dihydroxyazobenzene core (Bougueria et al, 2014;Evangelio et al, 2008;Schilde et al, 1994) and all of these are significantly less delocalized than 1Á2CHCl 3 .…”

Section: Database Surveymentioning

confidence: 99%

(E)-6,6′-(Diazene-1,2-diyl)bis(1,10-phenanthrolin-5-ol) trichloromethane disolvate: a superconjugated ligand

Ahmed¹,

Devereux²,

McKee³

et al. 2019

Acta Cryst E

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Phenanthroline ligands are important metal-binding molecules which have been extensively researched for applications in both material science and medicinal chemistry. Azobenzene and its derivatives have received significant attention because of their ability to be reversibly switched between the E and Z forms and so could have applications in optical memory and logic devices or as molecular machines. Herein we report the formation and crystal structure of a highly unusual novel diazo-diphenanthroline compound, C24H14N6O2·2CHCl3.

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1-[(E)-2-(5-tert-Butyl-2-hydroxyphenyl)diazen-1-yl]naphthalen-2-ol

Cited by 5 publications

References 9 publications

Crystal structure and Hirshfeld surface analysis of 1-[(E)-2-(5-chloro-2-hydroxyphenyl)hydrazin-1-ylidene]naphthalen-2(1H)-one

Crystal structure and Hirshfeld surface analysis of 1-[(E)-2-(5-chloro-2-hydroxyphenyl)hydrazin-1-ylidene]naphthalen-2(1H)-one

Crystal structure and Hirshfeld surface analysis of 1-[(E)-2-(3-nitrophenyl)diazen-1-yl]naphthalen-2-ol

(E)-6,6′-(Diazene-1,2-diyl)bis(1,10-phenanthrolin-5-ol) trichloromethane disolvate: a superconjugated ligand

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