Synthesis and Molecular Structure Investigation by DFT and X-Ray Diffraction of ARNO

Benhalima, Nadia; Toubal, Khaled; Chouaih, Abdelkader; Chita, Giuseppe; Maggi, S.; Djafri, Ayada; Hamzaoui, Fodil

doi:10.1007/s10870-011-0165-9

Cited by 18 publications

(9 citation statements)

References 13 publications

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“…All of the bond lengths are within normal ranges. Bond lengths and angles for the 5-(4-nitrobenzylidene)-3-(2-methoxyphenyl) moiety are consistent with those in related structures (Benhalima et al, 2011). As always, the thiazole ring is close to planar (r.m.s.…”

Section: Structural Commentarysupporting

confidence: 85%

Crystal and molecular structure of (2Z,5Z)-3-(2-methoxyphenyl)-2-[(2-methoxyphenyl)imino]-5-(4-nitrobenzylidene)thiazolidin-4-one

et al. 2017

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Section: Structural Commentarysupporting

confidence: 85%

Crystal and molecular structure of (2Z,5Z)-3-(2-methoxyphenyl)-2-[(2-methoxyphenyl)imino]-5-(4-nitrobenzylidene)thiazolidin-4-one

et al. 2017

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“…Recently, the synthesis and X-ray crystal structure of the title compound was published. 11 Based on these studies, and as a continuation of our previous work on thiazolidinone compounds [12][13][14][15] , herein, we report the optimized molecular structure as well as a detailed spectroscopic study on (2Z, 5Z)-3-N(4-methoxy phenyl)-2-N'(4-methoxy phenyl imino)-5-((E)-3-(2-nitrophenyl) allylidene) thiazolidin-4-one (MNTZ) using IR, 1 H and 13 C NMR spectra. The natural bond orbital (NBO) analysis is carried out to interpret intramolecular charge transfer (ICT).…”

Section: Introductionmentioning

confidence: 91%

Molecular Structure, FT-IR, NMR (13C/1H), UV-Vis Spectroscopy and DFT Calculations on (2Z, 5Z)-3-N(4-Methoxy phenyl)-2-N'(4-methoxy phenyl imino)-5-((E)-3-(2-nitrophenyl)allylidene) thiazolidin-4-one

Rahmani¹,

Djafri²,

Chouaih³

et al. 2019

S.Afr.j.chem.

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In this study, some molecular properties of (2Z, 5Z)-3-N(4-methoxy phenyl)-2-N'(4-methoxy phenyl imino)-5-((E)-3-(2-nitrophenyl) allylidene) thiazolidin-4-one (MNTZ) are evaluated using a combination of spectroscopic characterization (FT-IR, 1 H and 13 C NMR chemical shifts) and theoretical calculations. Molecular geometry, vibrational wavenumbers, gauge-independent atomic orbital (GIAO), 1 H and 13 C chemical shift values and NBO analysis are investigated using B3LYP and PBE functionals with the 6-31G(d,p) basis set in the ground state. The calculated geometrical parameters and vibrational spectra are compared to available experimental data and each vibrational frequency is assigned on the basis of potential energy distribution (PED). The electronic transitions are calculated using time-dependent density functional theory (TDDFT). The energy band gap between the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies are obtained by computing the frontier molecular orbitals using the B3LYP/6-31G(d,p) and PBE/6-31G(d,p) levels along with the global reactivity descriptors. Mulliken atomic charges and molecular electrostatic potential (MEP) are simulated using both functionals to find more reactive sites for electrophilic and nucleophilic attack. Finally, the thermodynamic functions (heat capacity, entropy, and enthalpy) from spectroscopic data are obtained and discussed in the range of 100-1000 K.

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“…The positions of the peaks marked with (2) in Fig. 8(a) these long spikes (indicated by (1) in Fig. 8) is characteristic of strong hydrogen bonds.…”

Section: Hirshfeld Surface Analysismentioning

confidence: 98%

“…The bond lengths are consistent with previous phenyl ring-containing studies. 1 In the thiazole moiety formed by C8, C9, C10, N1 and S1 …”

Section: Description Of the Crystal Structurementioning

confidence: 99%

“…Several theoretical and experimental investigations were performed to determine the absolute molecular con?guration of organic compounds containing fivemembered heterocyclic derivatives. [1][2][3] Among these types of compounds, 4-thiazolidinones have been shown to have various significant activities. Furthermore, thiazolidinone derivatives have been developed into useful materials for a variety of applications, such as of biological interest, nonlinear optical field and photovoltaic cells.…”

Section: Introductionmentioning

confidence: 99%

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Crystal Structure, Hirshfeld Surface Analysis and Computational Studies of Thiazolidin-4-one derivative: (Z)-5-(4-Chlorobenzylidene)-3-(2-ethoxyphenyl)-2-thioxothiazolidin-4-one

Khelloul

Toubal²,

Benhalima³

et al. 2016

ACSi

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The title compound (Z)-5-(4-chlorobenzylidene)-3-(2-ethoxyphenyl)-2-thioxothiazolidin-4-one (CBBTZ) was characterized by X-ray single crystal diffraction, 1 H NMR and 13 C NMR spectra. Theoretical investigations were carried out using HF and DFT levels of theory at 6-31G(d,p) basis set. The X-ray structure is compared with that computed. The calculated geometrical parameters are in good agreement with those determined by X-ray diffraction. The dihedral angle between the two benzene rings is 16.89(5)° indicating that the structure is non planar. The molecule exhibits intraand intermolecular contacts of type C-H···O, C-H···S and C-H···Cl. The intercontacts in the crystal structure are explored using Hirshfeld surfaces analysis method.

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Synthesis and Molecular Structure Investigation by DFT and X-Ray Diffraction of ARNO

Cited by 18 publications

References 13 publications

Crystal and molecular structure of (2Z,5Z)-3-(2-methoxyphenyl)-2-[(2-methoxyphenyl)imino]-5-(4-nitrobenzylidene)thiazolidin-4-one

Crystal and molecular structure of (2Z,5Z)-3-(2-methoxyphenyl)-2-[(2-methoxyphenyl)imino]-5-(4-nitrobenzylidene)thiazolidin-4-one

Molecular Structure, FT-IR, NMR (13C/1H), UV-Vis Spectroscopy and DFT Calculations on (2Z, 5Z)-3-N(4-Methoxy phenyl)-2-N'(4-methoxy phenyl imino)-5-((E)-3-(2-nitrophenyl)allylidene) thiazolidin-4-one

Crystal Structure, Hirshfeld Surface Analysis and Computational Studies of Thiazolidin-4-one derivative: (Z)-5-(4-Chlorobenzylidene)-3-(2-ethoxyphenyl)-2-thioxothiazolidin-4-one

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