Synthesis, structure and study of azo-hydrazone tautomeric equilibrium of 1,3-dimethyl-5-(arylazo)-6-amino-uracil derivatives

Debnath, Diptanu; Roy, Subhadip; Li, Bing Han; Lin, Chia Her; Misra, Tarun Kumar

doi:10.1016/j.saa.2014.12.027

Cited by 50 publications

(8 citation statements)

References 51 publications

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“…The synthesized dye (L) exhibited decreasing in intensity of π-π * transition at pH = 10 compared to parent azo and arising a new band at 550 nm which is due to ICT from OH (donor) to pyridine ring (accepter) during the azo functional (bridge) that meaning that the electronic transition involves the overall electronic system of the azo dye (L) ligand [19]. The spectrum of hydrazone form of (L) dye at pH = 2 appears little bit red shift and increasing in intensity for ππ * transition compared to parent azo form which is in agreement with the literatures [20][21][22][23]. These dramatic changes candidates this ligand a good example on the analytical indicators of acid-base like methyl orange which is azo dye.…”

Section: Resultssupporting

confidence: 89%

Synthesis, characterization, structure determination from powder X-ray diffraction data, and biological activity of azo dye of 3-aminopyridine and its complexes of Ni(II) and Cu(II)

Mohammed¹

2021

Bull. Chem. Soc. Eth.

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In the present work azo dye ligand of 3-aminopyridine (L) and its complexes of NiII and CuII were synthesized, characterized and evaluated for antibacterial and antifungal activities in vitro. The L ligand was synthesized by reacting diazonium ion of 3-aminopyridine with 1-naphthole in presence of sodium acetate. The ligand (L) and its complexes were characterized by elemental analysis (CHN), magnetic susceptibility, molar conductivity, UV-Vis spectra, and infrared technique. The (L) azo dye exhibited high sensing for the pH changes. The color of L dye changed from red in basic medium to yellow color in acidic medium. The data of CHN, UV-Vis and magnetic susceptibility indicate that the complexes [Ni(L)2Cl2] and [Cu(L)2Cl2] are tetrahedral. The complexes of Ni(II) and Cu(II) exhibited potent activity against growth of Staphylococcus aureus and Escherichia Coli as well as against Penicillium Sp. And Aspergillus niger. Under visible irradiation (395 nm), the (L) azo dye of pyridine exhibited a significant change in the spectra under irradiation. KEY WORDS: Pyridine, Photoisomerization, Pyridylazo, Biological activity, pH sensor Bull. Chem. Soc. Ethiop. 2020, 34(3), 523-532. DOI: https://dx.doi.org/10.4314/bcse.v34i3.8

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Section: Resultssupporting

confidence: 89%

Synthesis, characterization, structure determination from powder X-ray diffraction data, and biological activity of azo dye of 3-aminopyridine and its complexes of Ni(II) and Cu(II)

Mohammed¹

2021

Bull. Chem. Soc. Eth.

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“…Tautormeric equilibria of azo-hydrazone compounds was reported very recently, the azoenamine tautomer being the predominant form in the solid state, whereas the hydrazone-imine form is the preferred form in solution [7]. Structural properties of salicylhydrazone and aroylhydrazones derived from nicotinic acid hydrazide have been studied [8], the co-existence of…”

Section: Introductionmentioning

confidence: 99%

“…It was postulated that the large value of second order hyperpolarizability displayed by this kind of molecules is associated with an Internal Charge Transfer (ICT) process between electron-donor to electron-acceptor groups, facilitated by an extended conjugated  system. In this direction, a family of phenylhydrazono compounds containing the curcumin group was prepared and its structural and electronic properties were determined, showing that the frontier orbital energies are dependent on the electron-donor or electron-withdrawing nature of the substituent groups [6].Tautormeric equilibria of azo-hydrazone compounds was reported very recently, the azoenamine tautomer being the predominant form in the solid state, whereas the hydrazone-imine form is the preferred form in solution [7]. Structural properties of salicylhydrazone and aroylhydrazones derived from nicotinic acid hydrazide have been studied [8], the co-existence of…”

mentioning

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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“…[37] Generally, the relative intensities of these bands are strongly correlated to their equilibrium, which they are greatly influenced by the slight change in conditions (i. e. temperature, solvent and pH), due to the small free energy difference between them. [38] The side groups play also an important role at the tautomeric equilibrium via their electronic effects and intermolecular interactions (i. e. hydrogen bonding). Chen et al reported that the azo tautomer appeared at lower wavelength on contrary to the hydrazo tautomer.…”

Section: Uv-visible Absorption Spectra For the Synthesized Dyes (3-14)mentioning

confidence: 99%

Synthesis and In Vitro Evaluation of Anti‐Leukemic Potency of Some Novel Azo‐Naphthol Dyes Conjugated with Metal Nanoparticles as Photosensitizers for Photodynamic Therapy

et al. 2020

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Synthesis of some new mono azo organic compounds, based on 1‐arylazo‐2‐naphthol nucleus is performed by diazo‐coupling strategy of β‐naphthol with different 1ry aromatic amines. Interestingly, the monoazo products undergo functionalized reactions to obtain the target azo naphthol derivatives (3–14). The synthesized dyes are conjugated with gold and/ or silver nanoparticles by electrostatic interaction. Photodynamic therapeutic efficiencies of the synthesized naphthol azo dyes and their conjugates have been evaluated against promyelocytic leukemia cell lines (HL‐60) in dark and light conditions. Dye‐Nanometal conjugates act as photosensitizers (PSs) exhibiting an enhancement of the optical properties as well as in photodynamic therapeutic efficiencies in variable degrees depending on dye structure.

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Synthesis, structure and study of azo-hydrazone tautomeric equilibrium of 1,3-dimethyl-5-(arylazo)-6-amino-uracil derivatives

Cited by 50 publications

References 51 publications

Synthesis, characterization, structure determination from powder X-ray diffraction data, and biological activity of azo dye of 3-aminopyridine and its complexes of Ni(II) and Cu(II)

Synthesis, characterization, structure determination from powder X-ray diffraction data, and biological activity of azo dye of 3-aminopyridine and its complexes of Ni(II) and Cu(II)

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

Synthesis and In Vitro Evaluation of Anti‐Leukemic Potency of Some Novel Azo‐Naphthol Dyes Conjugated with Metal Nanoparticles as Photosensitizers for Photodynamic Therapy

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