Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-(4-methoxyphenyl)-3-cyano-2-pyridone dyes: Hydrazone-azo tautomeric analysis

Alimmari, Adel S.; Božić, Bojan; Mijin, Dušan Ž.; Marinković, Aleksandar D.; Valentić, Nataša V.; Ušćumlić, Gordana S.

doi:10.1016/j.arabjc.2013.10.001

Cited by 29 publications

(16 citation statements)

References 22 publications

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“…ACCEPTED MANUSCRIPT 4 4 two tautomeric forms was determined for the solid substance, as well as for highly concentrated solutions, whereas only the hydrazone tautomer is present in diluted solutions [9,10]. It is anticipated that the formation of inter-and intra-molecular hydrogen bonds strongly influence these equilibria [11].…”

Section: Accepted Manuscriptmentioning

confidence: 99%

On the roles of close shell interactions in the structure of acyl-substituted hydrazones: An experimental and theoretical approach

Saeed

Arshad

Bolte

et al. 2016

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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The 2-(phenyl-hydrazono)-succinic acid dimethyl ester compound was synthesized by reacting phenylhydrazine with dimethylacetylene dicarboxylate at room temperature and characterized by elemental analysis, infrared, Raman, (1)H and (13)C NMR spectroscopies and mass spectrometry. Its solid state structure was determined by X-ray diffraction methods. The X-ray structure determination corroborates that the molecule is present in the crystal as the hydrazone tautomer, probably favored by a strong intramolecular N-H···O=C hydrogen bond occurring between the carbonyl (-C=O) and the hydrazone -C=N-NH- groups. A substantial fragment of the molecular skeleton is planar due to an extended π-bonding delocalization. The topological analysis of the electron densities (Atom in Molecule, AIM) allows characterization of intramolecular N-H···O interaction, that can be classified as a resonant assisted hydrogen bond (RAHB). Moreover, the Natural Bond Orbital population analysis confirms that a strong hyperconjugative lpO1→σ*(N2-H) remote interaction between the C2=O1 and N2-H groups takes place. Periodic system electron density and topological analysis have been applied to characterize the intermolecular interactions in the crystal. Weak intermolecular interactions determine the crystal packing, and the prevalence of non-directional dispersive contributions are inferred on topological grounds. The IR spectrum of the crystalline compound was investigated by means of density functional theory calculations carried out with periodic boundary conditions on the crystal, showing excellent agreement between theory and the experiments. The vibrational assignment is complemented with the analysis of the Raman spectrum.

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Section: Accepted Manuscriptmentioning

confidence: 99%

On the roles of close shell interactions in the structure of acyl-substituted hydrazones: An experimental and theoretical approach

Saeed

Arshad

Bolte

et al. 2016

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…Generally, a solvatochromic material can be defined as a chemical substance able to alter its color in solvents of different polarities due to a variation in its absorption or emission spectra in each solvent. ere is a variety of solvatochromic dyes that have been discovered recently, such as pyridinium, merocyanine, and stilbazolium dyes [9][10][11][12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Solvatochromic Performance, pH Sensing, Dyeing Ability, and Antimicrobial Activity of Novel Hydrazone Dyestuffs

Khattab

Allam

Othman

et al. 2019

Journal of Chemistry

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New tricyanofuran intramolecular charge transfer dyes comprising the hydrazone group were prepared and fully characterized in order to study their possible solvatochromism, dyeing ability, and antimicrobial activity. e preparation of the hydrazone dyes was achieved in relatively good yields starting from different aromatic amines. e hydrazone functional group was presented via the azo-coupling reaction of the tricyanofuran compound by the properly substituted diazonium chloride. Chemical structures of the prepared hydrazones were confirmed via nuclear magnetic resonance spectroscopy ( 1 H-and 13 C-NMR), Fourier-transform infrared spectroscopy (FT-IR), and elemental analysis (C, H, and N). e UV-visible absorption spectra of the produced sensor colorants displayed interesting solvatochromism in solvents with a different polarity, which was found to be affected by the substituents bonded to the aromatic hydrazone moiety. e pH molecular switching was investigated through tuning the intramolecular charge transfer stimulated by the reversible deprotonation/protonation process in acetonitrile solution showing color change from yellow to purple. e produced disperse dyestuffs were employed for dyeing polyester fibers to introduce acceptable color strength and colorfastness properties. Moreover, the dyes verified a weak to moderate antimicrobial activity against some selected pathogens, including S. aureus, E. coli, and Candida albicans.

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“…More than 50% colorants with the azo group are most widely employed in areas of dyeing such as that of textile fibers and in coloration of various materials. Their applications in advanced organic synthesis and biological and medical fields are well recognized [1][2][3]. Antibacterial activity of azo compounds and their metal chelates have also been reported [4].…”

Section: Introductionmentioning

confidence: 99%

DFT Study for the Spectroscopic and Structural Analysis of p-Dimethylaminoazobenzene

Ali

Mansha

Asim

et al. 2018

Journal of Spectroscopy

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The study under consideration represents the computational calculations of Azo-based direct dye named p-(dimethylamino)azobenzene (DMAB) under the effect of solvents with different relative permittivities. A density functional theory (DFT) method at the B3LYP level with 6-311G++ was applied for the spectroscopic and structural analysis of the title compound. Calculations of geometric parameters (bond orders, bond lengths, and dihedral angles), electron densities, thermodynamic parameters, and orbital energies were performed for the title compound. Mulliken population analysis (MPA) as well as natural population analysis (NPA) was also performed at the B3LYP level with different solvents for finding solvent effects. In order to predict the reactivity of DMAB, molecular electrostatic potential (MESP) calculations were carried out for it. For vibrational analysis, the infrared (IR) spectra were computed for the title compound at the B3LYP/6-311G++ level in the gas phase and in different solvents with good agreement to the experimental FT-IR spectrum. The different modes of vibrations were assigned using potential energy distribution (PED). The computed Raman spectra also showed appreciable agreement with the experimental recorded Raman spectrum. The electronic absorption spectra of the title compound have been computed employing DFT/B3LYP with the 6-311G++ basis set in the gas phase and in four different solvents, that is, DMSO, ethanol, acetonitrile, and water which were compared with the experimental spectra with appreciable agreement. NBO analysis was carried out for understanding the intramolecular and intermolecular bonding of the compound and the density transfer from completely filled to unfilled orbital was found. The HOMO-LUMO energies were determined for analyzing the mechanism of intramolecular charge transfer.

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Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-(4-methoxyphenyl)-3-cyano-2-pyridone dyes: Hydrazone-azo tautomeric analysis

Cited by 29 publications

References 22 publications

On the roles of close shell interactions in the structure of acyl-substituted hydrazones: An experimental and theoretical approach

On the roles of close shell interactions in the structure of acyl-substituted hydrazones: An experimental and theoretical approach

Synthesis, Solvatochromic Performance, pH Sensing, Dyeing Ability, and Antimicrobial Activity of Novel Hydrazone Dyestuffs

DFT Study for the Spectroscopic and Structural Analysis of p-Dimethylaminoazobenzene

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