Crystal structure of 1,1′-{(dodecane-1,12-diyl)bis[(azaniumylylidene)methanylylidene]}bis(naphthalen-2-olate)

Ouari, Kamel; Merzougui, Moufida; Bendia, Sabrina; Bailly, Corinne

doi:10.1107/s2056989015007938

Cited by 3 publications

(1 citation statement)

References 20 publications

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“…observed in the keto form, in the enol form or in enol/keto mixtures [7,8]. Another form of the Schiff base compounds is also their zwitterionic form [9][10][11][12]. Zwitterions of Schiff bases have an ionic intramolecular hydrogen bond (N + -H• • •O -) and their N + -H bond lengths are longer than the standard interatomic separations observed in neutral N-H bonds (0.87 Å).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, X-ray crystallography, computational studies and catecholase activity of new zwitterionic Schiff base derivatives

Boulemche

Anak

Djedouani

et al. 2019

Journal of Molecular Structure

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Three new Schiff bases compounds (L1-L2-L3) were synthesized by a condensation reaction in 1:1 molar ratios of dehydroacetic acid (3-acetyl-6-methyl-2H-pyran-2,4(3H)-dione) and 4-fluoro/4chloro/4-bromo aniline in ethanol, the products were obtained in excellent yields. Their structures were characterized by spectroscopic techniques (FT-IR and 1H-NMR) and single-crystal X-ray diffraction. The three compounds display zwitterionic forms, with cationic iminium and anionic enolate groups.The aromatic ring and dehydroacetic acid ring are in a trans position with respect to the C=N bond. Calculations in the framework of the density-functional theory (DFT) were carried out to determine the optimized structures and electronic properties as the HOMO-LUMO energy gap.Hirshfeld surface analysis was used to support the packed crystal lattice 3D network intermolecular forces. The NH form is found to be more stable than OH form. On the other hand, the in situ generated copper (II) complexes were examined for their catalytic activities and were found to catalyze the oxidation reaction of catechol to o-quinone under atmospheric dioxygen. The present study reveals that the rate of oxidation depends on the nature of the substituents in the phenyl ring, the counter anion and the concentration of ligand. The combination L1(Cu(CH3COO)2) gives the highest rate.

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Section: Introductionmentioning

confidence: 99%

Synthesis, X-ray crystallography, computational studies and catecholase activity of new zwitterionic Schiff base derivatives

Boulemche

Anak

Djedouani

et al. 2019

Journal of Molecular Structure

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Crystal structure of 1,1′-{(pentane-1,5-diyl)bis[(azaniumylylidene)methanylylidene]}bis(naphthalen-2-olate)

Ouari¹,

Merzougui²,

Karmazin³

2015

Acta Cryst E

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1,1′-{(1E,1′E)-[Octane-1,8-diylbis(azanylylidene)]bis(methanylylidene)}bis(naphthalen-2-ol) in the zwitterionic form

2017

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The title compound, C30H32O2N2, is formed from two units ofortho-hydroxynaphthaldehyde bridged with 1,8-diaminooctane. In the solid state, it exists as a double zwitterion. The N atoms are protonated and the C—O−bonds lengths are 1.265 (2) Å, with intramolecular N—H...O hydrogen bonds formingS(6) ring motifs. The molecule has twofold rotational symmetry, with the twofold axis bisecting the central –CH2—CH2– bond of the bridging octane chain. In the crystal, molecules are linked by N—H...O hydrogen bonds, forming chains propagating along the [-201] direction. The chains are linkedviaC—H...O hydrogen bonds, forming a supramolecular three-dimensional framework structure.

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Crystal structure of 1,1′-{(dodecane-1,12-diyl)bis[(azaniumylylidene)methanylylidene]}bis(naphthalen-2-olate)

Cited by 3 publications

References 20 publications

Synthesis, X-ray crystallography, computational studies and catecholase activity of new zwitterionic Schiff base derivatives

Synthesis, X-ray crystallography, computational studies and catecholase activity of new zwitterionic Schiff base derivatives

Crystal structure of 1,1′-{(pentane-1,5-diyl)bis[(azaniumylylidene)methanylylidene]}bis(naphthalen-2-olate)

1,1′-{(1E,1′E)-[Octane-1,8-diylbis(azanylylidene)]bis(methanylylidene)}bis(naphthalen-2-ol) in the zwitterionic form

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