Synthesis, molecular and solid state structure of 5-(5-nitro furan-2-ylmethylen), 3- N -(2-methoxy phenyl), 2- N ′-(2-methoxyphenyl) imino thiazolidin-4-one: X-ray powder diffraction and DFT studies

Rahmani, Rachida; Djafri, Ahmed; Chouaih, Abdelkader; Djafri, Ayada; Hamzaoui, Fodil; Rizzi, Rosanna; Altomare, Angela

doi:10.1016/j.molstruc.2017.04.091

Cited by 14 publications

(2 citation statements)

References 26 publications

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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: 90%

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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Section: Introductionmentioning

confidence: 90%

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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“…Firstly, we will consider the case of 5-(5-nitro furan-2-ylmethylen), 3-N-(2-methoxy phenyl), 2-N'-(2-methoxyphenyl) imino thiazolidin-4-one compound [9] with chemical formula C 22 H 17 O 6 N 3 S. X-ray diffraction data, shown in Figure 3, were collected at room temperature (293 K) by using an automated Rigaku RINT2500 laboratory diffractometer (50 KV, 200 mA), equipped with an asymmetric Johansson Ge(111) crystal to select the monochromatic CuKa1 radiation (λ = 1.54056 Å). The silicon strip Rigaku D/teX Ultra detector was used.…”

Section: Solving Structures In the Reciprocal Space By Expo: Case Stumentioning

confidence: 99%

Solving a Structure in the Reciprocal Space, Real Space and Both by Using the EXPO Software

et al. 2019

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The solution of crystal structures from X-ray powder diffraction data has undergone an intense development in the last 25 years. Overlapping, background estimate, preferred orientation are the main difficulties met in the process of determining the crystal structure from the analysis of the one-dimensional powder diffraction pattern. EXPO is a well known computer program that, designed for solving structures, organic, inorganic, as well as metal-organic by powder diffraction data, employs the two most widely used kinds of solution methods: Direct Methods proceeding in the reciprocal space and Simulated Annealing proceeding in the real space. EXPO allows also to suitably combine these two approaches for validating the structure solution. In this paper, we give examples of structure characterization by EXPO with the aim of suggesting a solution strategy leading towards the application of reciprocal-space methods or real-space methods or both.

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Thiazoles

Chotera-Ouda

Wróblewska

Tokarz

et al. 2022

Comprehensive Heterocyclic Chemistry IV

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Synthesis, molecular and solid state structure of 5-(5-nitro furan-2-ylmethylen), 3- N -(2-methoxy phenyl), 2- N ′-(2-methoxyphenyl) imino thiazolidin-4-one: X-ray powder diffraction and DFT studies

Cited by 14 publications

References 26 publications

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

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

Solving a Structure in the Reciprocal Space, Real Space and Both by Using the EXPO Software

Thiazoles

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