Studies on the synthesis, spectroscopic analysis and DFT calculations on (E)-4,6-dichloro-2-[(2-chlorophenylimino)methyl]-3methoxyphenol as a novel Schiff's base

Yıldırım, Arzu Özek; Yıldırım, M. Hakkı; Kaştaş, Çiğdem Albayrak

doi:10.1016/j.molstruc.2016.02.041

Cited by 18 publications

(4 citation statements)

References 71 publications

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“…The 1,2,3-triazole rings are planar, with maximum deviation from the plane of only 0.0063 Å (N8, N9, N10, C40, C39) and 0.0049 Å (N3, N4, N5, C16, C15). The Schiff base (N6=C37 and N1=C13) average bond length is 1.2855 Å, which is close to the corresponding values previously reported as 1.272 Å [ 30 ], 1.269 Å [ 31 ], and 1.283 Å [ 32 ]. The dihedral angles between planes A (C1/2/3/4/5/6), B (C7/8/9/10/11/12), C (1,2,3-triazole ring; N3, N4, N5, C16, C15), and D (C18/19/20/21/22/23) are 85.320° (A/B), 65.823° (A/C), 71.638° (A/D), 19.929° (B/C), 26.276° (B/D), and 43.343° (C/D).…”

Section: Resultssupporting

confidence: 88%

Quantum Computational Investigation of (E)-1-(4-methoxyphenyl)-5-methyl-N′-(3-phenoxybenzylidene)-1H-1,2,3-triazole-4-carbohydrazide

et al. 2022

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The title compound was synthesized and structurally characterized. Theoretical IR, NMR (with the GIAO technique), UV, and nonlinear optical properties (NLO) in four different solvents were calculated for the compound. The calculated HOMO–LUMO energies using time-dependent (TD) DFT revealed that charge transfer occurs within the molecule, and probable transitions in the four solvents were identified. The in silico absorption, distribution, metabolism, and excretion (ADME) analysis was performed in order to determine some physicochemical, lipophilicity, water solubility, pharmacokinetics, drug-likeness, and medicinal properties of the molecule. Finally, molecular docking calculation was performed, and the results were evaluated in detail.

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Section: Resultssupporting

confidence: 88%

Quantum Computational Investigation of (E)-1-(4-methoxyphenyl)-5-methyl-N′-(3-phenoxybenzylidene)-1H-1,2,3-triazole-4-carbohydrazide

et al. 2022

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“…It is H→L (53%) and H-1→L (41%), respectively. The experimental values coincide with the calculated λmax [36]. The calculated and experimental UV visible spectral values, such as energy, oscillator strength, and λmax for compound 2 are compared in Table 6.…”

Section: Uv-vis Data and Fmo Analysissupporting

confidence: 64%

Comparative study of 4-((4-aminophenyl)diazenyl)-2-((2-phenylhydrazono)methyl)phenol and N-(4-((4-hydroxy-3-((2-phenylhydrazono)methyl)phenyl)diazenyl)phenyl)acetamide - DFT method

Siluvairaj,

Govindasamy,

Govindasamy

et al. 2024

Eur J Chem

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Theoretical calculation of 4-((4-aminophenyl)diazenyl)-2-((2-phenylhydrazono)methyl) phenol (1) and N-(4-((4-hydroxy-3-((2-phenylhydrazono)methyl)phenyl)diazenyl)phenyl) acetamide (2) was studied by DFT/B3LYP/6-311+G(d,p) basis set. The calculated values of geometric structural parameters, Fourier transform infrared spectral data, highest occupied molecular orbital and lowest unoccupied molecular orbital, natural bond orbital, nucleus-independent chemical shifts, Fukui function, polarizability, hyperpolarizability, and UV data of compounds 1 and 2 clearly indicate that substitution of the amino group alters the physical properties of compound 2. The nucleus-independent chemical shift values of the amino-substituted phenyl ring reduces the aromatic character due to the lone pair electron on nitrogen involved in inductive and conjunction effects, as well as due to OH, NH2 and OH, NHCOCH3 in compounds 1 and 2, respectively. The effect of the solvent on different parameters was studied, and it was found that increasing the dielectric constant increased the parameter studied. The stability and planarity of the molecule’s effects on dipole moment, energy, polarizability, and hyperpolarizability were studied extensively.

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“…They are N−H⋅⋅⋅O and O−H⋅⋅⋅N hydrogen bonds in keto‐amine and enol‐imine tautomers, respectively . Various methods were utilized to indicate the existence of the keto–amine and enol–imine tautomerism such as X‐ray crystallography, FT‐IR, UV‐Vis, 13 C‐NMR and 1 H‐NMR methods …”

Section: Introductionmentioning

confidence: 99%

DFT Quantum Chemical Studies on Structural, Nonlinear Optical, Reactivity and Thermodynamic Properties of 4‐Methoxy‐2‐{(E)‐[(thiophen‐2‐yl)ethylimino]methyl}phenol

Tanak

2019

ChemistrySelect

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The molecular structure of 4-Methoxy-2-{(E)-[(thiophen-2-yl) methylimino]methyl}phenol was optimized using the PBEPBE, B3PW91 and B3LYP methods with the 6-311 + + G(d,p) basis set and compared to experimental X-ray data. Density functional computations of the interaction energies, molecular electrostatic potential, and thermodynamic functions have been carried out using the B3LYP method with the 6-311 + + G(d,p) basis set for the title molecule. The chemical reactivity behaviors of the tautomeric forms of the compound were analyzed at the B3LYP/6-311 + + G(d,p) level. Additionally, the solvent effects have been investigated with the integral equation formalism polarizable continuum model. The dipole moment, first hyperpolarizability and linear polarizability values of the tautomeric forms of the compound were computed using the B3LYP/6-311 + + G(d,p) method. The changes of the entropy, enthalpy and Gibbs free energy for the formation reaction of the compound have been predicted in different temperature utilizing the statistical thermodynamical technique. Computational detailsAll quantum chemical computations have been carried out using the Gaussian 09 W program package. [29] The calculated results were visualized by GaussView 5.0. [30] Experimental molecular geometry was utilized as the initial guess for optimization. Geometry optimizations were performed by DFT utilizing the B3LYP, [31] B3PW91 [32] and PBEPBE [33] functionals with the 6-311 + + G(d,p) basis set. Cartesian coordinates of the optimized structures of MTMP have been given in the [a] Prof.

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Studies on the synthesis, spectroscopic analysis and DFT calculations on (E)-4,6-dichloro-2-[(2-chlorophenylimino)methyl]-3methoxyphenol as a novel Schiff's base

Cited by 18 publications

References 71 publications

Quantum Computational Investigation of (E)-1-(4-methoxyphenyl)-5-methyl-N′-(3-phenoxybenzylidene)-1H-1,2,3-triazole-4-carbohydrazide

Quantum Computational Investigation of (E)-1-(4-methoxyphenyl)-5-methyl-N′-(3-phenoxybenzylidene)-1H-1,2,3-triazole-4-carbohydrazide

Comparative study of 4-((4-aminophenyl)diazenyl)-2-((2-phenylhydrazono)methyl)phenol and N-(4-((4-hydroxy-3-((2-phenylhydrazono)methyl)phenyl)diazenyl)phenyl)acetamide - DFT method

DFT Quantum Chemical Studies on Structural, Nonlinear Optical, Reactivity and Thermodynamic Properties of 4‐Methoxy‐2‐{(E)‐[(thiophen‐2‐yl)ethylimino]methyl}phenol

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