Some polyhydroxy azo–azomethine derivatives of salicylaldehyde: Synthesis, characterization, spectroscopic, molecular structure and antimicrobial activity studies

Odabaşoğlu, Mustafa; Albayrak, Çiğdem; Özkanca, Reşit; Aykan, Fatma Zehra; Lonecke, Peter

doi:10.1016/j.molstruc.2006.11.025

Cited by 117 publications

(57 citation statements)

References 23 publications

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“…Besides the C17-C21-O23-C24, C16-C20-O22-C23, C19-C21-O23-C24 and C18-C20-O22-C23 planes are inclined by 69.0º, 68.40º, -117.7º and -117.81º in the skeleton from the molecular plane of the both compounds, respectively. The structural parameters obtained from computed methods are in good agreement with the literature values [18].…”

Section: Spectral Measurementssupporting

confidence: 86%

“…The carbonyl stretching vibrations are expected in the region between 1715 -1680 cm -1 [18,24,25]. In our case, two C=O stretching bands were observed in both experimental FT-IR and FT-Raman spectra.…”

Section: C=o Vibrations Of Fpmc and Cfpmcsupporting

confidence: 56%

“…Besides, from the above results compared to the C-C bond lengths of benzene (1) ring was found to be significantly small within 0.01-0.02 Å for CFPMC than that of FPMC due to chlorine atom in C1 carbon of CFPMC and the C-C bond lengths of with carbonate attached benzene ring is increases in both compounds (C16-C19/C15-C18) due to carbonate group attachment. The bond length values of C4-N12/C4-N11 (1.42/1.42/1.43 Å), N13-C14/N12-C13 (1.42/1.42/1.43 Å) are found to coincide with related compounds [18].…”

Section: Spectral Measurementsmentioning

confidence: 78%

“…In the first step, 2-hydroxy-5-(phenyldiazenyl)benzaldehyde (HPDB) and 5-((4-chlorophenyl)diazenyl)-2-hydroxybenzaldehyde (CPDB) have been synthesized according to the procedure as mentioned in literature [18] and the second step reaction, the reaction between HPDB and methyl chloroformate were carried out in different solvents in order to study about the feasibility of the reaction. Optimization of reaction conditions is shown in Table 1 and DCM/K 2 CO 3 yielded the product quantitatively (Entry 4).…”

Section: Synthesis Of Fpmc and Cfpmcmentioning

confidence: 99%

“…6631+G(d, p). The calculated structural parameters have been compared with the crystal structure of azo compounds available in the literature [18,24]. The calculated structural parameters of FPMC and CFPMC are depicted in Tables 8 and 9, respectively.…”

Section: Spectral Measurementsmentioning

confidence: 99%

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Synthesis, Spectroscopic Investigation and Computational Studies of 2-Formyl-4-(Phenyldiazenyl)Phenyl Methyl Carbonate and 4-((4-Chlorophenyl)Diazenyl)-2-Formylphenyl Methyl Carbonate

Arokiasamy

Manikandan

Thanikachalam

et al. 2016

ILCPA

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ABSTRACT. Two new compounds namely 2-formyl-4-(phenyldiazenyl)phenyl methyl carbonate (FPMC) and 4-((4-chlorophenyl) diazenyl)-2-formylphenyl methyl carbonate (CFPMC) have been synthesized and have characterized using FT-IR, FT-Raman, 1 H and 13 C NMR techniques. Computational optimization studies have been carried out using Hatree-Fock (HF) and Density Functional Theory (DFT-B3LYP) methods with 6-31+G(d, p) basis set of Gaussian 09W software. The stable configuration of the title compounds were achieved theoretically by potential energy surface scan analysis. The complete vibrational assignments were performed on the basis of total energy distribution (TED) and natural bonding orbital (NBO) have been studied. Various parameters such as E HOMO , E LUMO , total energy, dipole moment, polarizability, first order hyperpolarizability, zero-point vibrational energy as well as thermal properties were analyzed and reported for the title compounds.

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Section: Spectral Measurementssupporting

confidence: 86%

Section: C=o Vibrations Of Fpmc and Cfpmcsupporting

confidence: 56%

Section: Spectral Measurementsmentioning

confidence: 78%

Section: Synthesis Of Fpmc and Cfpmcmentioning

confidence: 99%

Section: Spectral Measurementsmentioning

confidence: 99%

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Synthesis, Spectroscopic Investigation and Computational Studies of 2-Formyl-4-(Phenyldiazenyl)Phenyl Methyl Carbonate and 4-((4-Chlorophenyl)Diazenyl)-2-Formylphenyl Methyl Carbonate

Arokiasamy

Manikandan

Thanikachalam

et al. 2016

ILCPA

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A novel azo‐azomethine benzoxazole‐based ligand and its transition metal (II), (III), (IV) complexes: Synthesis, characterization, theoretical studies, biological evaluation, and catalytic application

Bakr

Atteya

Al‐Hefnawy

et al. 2023

Applied Organom Chemis

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This work describes the synthesis of a novel multiple dentation azo-Schiff base dye 2- ((3-((5-chlorobenzo[d]oxazol-2-yl)diazenyl)-4-hydroxybenzylidene) amino)pyridin-3-ol (H 2 L) based mixed heterocyclic bnzoxazole and pyridine moieties in facile two successive steps approach. Firstly is the synthesis of start azo dye 3- ((5-chlorobenzo[d]oxazol-2-yl)diazenyl)-4-hydroxybenzaldehyde (CBOAHB) followed by condensation with 3-hydroxy 2-amino pyridine. It's novel binuclear Ni (II), Cu (II), Ru (III), and Zr (IV) 2:1 metal-to-ligand stoichiometric complexes were synthesized and characterized via various spectroscopic and analytical techniques. The data showed the paramagnetic Ni 2+ complex has tetrahedral geometry, while the Cu 2+ , Ru 3+ , and diamagnetic Zr 4+ complexes have octahedral geometrical structures. Data of the crystallinity, morphology, and average particle size showed that Cu 2+ and Ru 3+ complexes were formed at the nanoscale. The geometrical structures according to 3D molecular modeling are in good agreement with those proposed by the experiments. The azo start CBOAHB, H 2 L, and its metal complexes have been examined for their biological and catalytic features. The Zr 4+ complex manifested higher antibacterial activity against Staphylococcus aureus (S. aureus), the ligand H 2 L exhibited higher antibacterial activity against Escherichia coli (E. coli), and the Ni 2+ complex showed higher antifungal activity against Candida albicans (C. Albicans). The anticancer activity was evaluated against human hepatocellular carcinoma (HepG-2), colorectal carcinoma (HCT-116), and human breast carcinoma (MCF-7). The ligand H 2 L has very strong cytotoxicity toward HepG-2 cells, Ni (II) complex has the strongest cytotoxicity against HCT-116 cells and Zr (VI) has the strongest cytotoxicity against MCF-7 cells. The findings of antioxidant activity are in perfect accord with those obtained from anticancer. The heterogeneous catalytic activity was examined for the reduction of Direct Blue 14 dye. Ru (III) complex and Cu (II) complex achieved the highest catalytic activity with the highest degradation % and within a very short time did not exceed 3 min.

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Schiff Bases from TRIS and ortho‐Hydroxyarenecarbaldehydes: Structures and Tautomeric Equilibria in the Solid State and in Solution

Martínez¹,

Авалос²,

Babiano³

et al. 2011

Eur J Org Chem

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Three Schiff bases generated by conventional condensation of a simple aminopolyol (TRIS) and 5‐bromo‐ and 5‐iodosalicylaldehyde, and 2‐hydroxy‐1‐naphthaldehyde, have been fully characterized, both in solution and in the solid state. This study provides a complete analysis of imine–enamine equilibria, and sheds light onto the mechanism of hydrogen transfer, which has been controversial in the literature. Low‐temperature X‐ray diffraction accompanied by electron‐density maps have further been complemented by theoretical studies at the B3LYP/6‐31G* and M06‐2X/6‐311++G** levels. To ascertain the influence of crystal packing on tautomeric stability, the lattice has also been simulated by computation. This protocol involves the assessment of a supramolecular cluster around a core tautomer possessing either imine or enamine structures. Such an analysis, in full agreement with solid‐state data, reveals the greater stability of zwitterionic structures for the salicyl derivatives. In contrast, these substances show preferential imine forms in solution, whereas the naphthyl‐based compound exhibits a prevalent keto‐enamine structure in all cases.

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Some polyhydroxy azo–azomethine derivatives of salicylaldehyde: Synthesis, characterization, spectroscopic, molecular structure and antimicrobial activity studies

Cited by 117 publications

References 23 publications

Synthesis, Spectroscopic Investigation and Computational Studies of 2-Formyl-4-(Phenyldiazenyl)Phenyl Methyl Carbonate and 4-((4-Chlorophenyl)Diazenyl)-2-Formylphenyl Methyl Carbonate

Synthesis, Spectroscopic Investigation and Computational Studies of 2-Formyl-4-(Phenyldiazenyl)Phenyl Methyl Carbonate and 4-((4-Chlorophenyl)Diazenyl)-2-Formylphenyl Methyl Carbonate

A novel azo‐azomethine benzoxazole‐based ligand and its transition metal (II), (III), (IV) complexes: Synthesis, characterization, theoretical studies, biological evaluation, and catalytic application

Schiff Bases from TRIS and ortho‐Hydroxyarenecarbaldehydes: Structures and Tautomeric Equilibria in the Solid State and in Solution

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