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, Nawel; Toubal, Khaled; Benhalima, Nadia; Rahmani, Rachida; Chouaih, Abdelkader; Djafri, Ayada; Hamzaoui, Fodil

doi:10.17344/acsi.2016.2362

Cited by 20 publications

(9 citation statements)

References 24 publications

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“…Bond angles C6-N2-C1, C2-N1-C4 and C1-N1-C4 are also near 120° (119.56°, 121.08° and 116.72°, respectively). 26 The bond angles centered on C1 are all between 109° and 129°. The C1 atom is of sp 2 hybridization type because the total adds up to 360° at B3LYP/6-311G(d,p) level.…”

Section: Structure Descriptionmentioning

confidence: 99%

Synthesis, X-Ray Structure Determination and Related Physical Properties of Thiazolidinone Derivative by DFT Quantum Chemical Method

Megrouss

Baara

Boukabcha

et al. 2019

ACSi

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In this paper we report the synthesis and characterization of the (Z)-3-N-(ethyl)-2-N'-((3-methoxyphenyl)imino)thiazolidine-4-one by means of FT-IR, 1 H and 13 C NMR and by single crystal X-ray diffraction. The experimental determination of the crystal structure of the compound has been achieved using X-ray diffraction data. The important characteristic of the structure is the existence of a dihedral angle formed by the benzene and thiazolidinone rings being equal to 86.0° indicating an absence of π-π stacking as well as that the structure is non planar. In the crystal, the molecules are linked by C-H···O and C-H···N hydrogen bonds, these bonds being responsible for the three-dimensional molecular structure packing. In order to compare the experimental results with those of the theoretical calculation, quantum chemical DFT calculations were carried out using B3LYP/6-311G(d,p) basis set. In this context, the molecular electrostatic potential around the molecule and HOMO-LUMO energy levels were also computed. The dipole moment orientations were determined in order to understand the nature of inter-and intramolecular charge transfer. Finally, the stability of the title compound was confirmed throughout the calculation of the chemical reactivity descriptors.

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Section: Structure Descriptionmentioning

confidence: 99%

Synthesis, X-Ray Structure Determination and Related Physical Properties of Thiazolidinone Derivative by DFT Quantum Chemical Method

Megrouss

Baara

Boukabcha

et al. 2019

ACSi

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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%

“…Synthesis, solid state structure and spectral data (IR, 1 H NMR, 13 C NMR) of the title compound are reported in our previous work. 11 IR spectra were recorded in KBr pellet on a JASCO FT/IR 4210 Fourier Transform Infrared Spectrometer and the reported wave numbers were given in cm -1 .…”

Section: Experimental and Computational Detailsmentioning

confidence: 99%

“…11 IR spectra were recorded in KBr pellet on a JASCO FT/IR 4210 Fourier Transform Infrared Spectrometer and the reported wave numbers were given in cm -1 . The 1 H NMR and 13 C NMR were recorded on Brüker Ac DPX-200(300 MHz) spectrometer in CDCl 3 as solvent using tetramethylsilane as an internal reference standard.…”

Section: Experimental and Computational Detailsmentioning

confidence: 99%

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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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“…C2=O2 bond distances are also shown to have a typical double bond character with lengths of 1.196(1) Å and 1.201(1) Å, respectively. 24 The C3-C4-C5 angles are 129.90(1)⁰ and 129.62(1)⁰, respectively, being quite large. These angle values and the exocyclic angles of C3 and C5 (Table 2) are in accordance with the repulsive intramolecular interactions between the N1 and H10 atoms, similar to the oxazol-5-one derivatives reported previously.…”

Section: Crystal Structurementioning

confidence: 97%

Spectroscopic, Structural and Density Functional Theory (DFT) Studies of Two Oxazol-5-one Derivatives

Nazlı

Celepci²,

Yakalı³

et al. 2018

ACSi

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In this study, two oxazol-5-one derivatives, C 20 H 20 N 2 O 2 (1) and C 21 H 22 N 2 O 2 (2), were synthesized by getting condensed p-N,N-diethylaminobenzaldehyde with two presented hippuric acid derivatives and in further studies they were analysed spectrochemically. Molecular and crystal structures of the compounds were determined by single-crystal X-ray diffraction and the results revealed that the molecular packing of the crystal structures were stabilized by weak intraand intermolecular interactions also with C-O•••π, C-H•••π and π•••π stacking interactions. Computational studies were also performed using DFT method at B3LYP/6-311G(d,p) level of theory. Vibrational modes and chemical shifts were calculated and compared with the experimental data. In addition, frontier molecular orbitals and molecular electrostatic potential surfaces were simulated. The calculated results show that the optimized geometries can well reproduce the crystal structure. Purpose of this study was to survey the effects of the reactants, which were condensed with each other to produce oxazol-5-one, upon the characteristic properties and crystal forms of the final oxazol-5-one.

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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

Cited by 20 publications

References 24 publications

Synthesis, X-Ray Structure Determination and Related Physical Properties of Thiazolidinone Derivative by DFT Quantum Chemical Method

Synthesis, X-Ray Structure Determination and Related Physical Properties of Thiazolidinone Derivative by DFT Quantum Chemical Method

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

Spectroscopic, Structural and Density Functional Theory (DFT) Studies of Two Oxazol-5-one Derivatives

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