Crystal structure and spectral of new hydrazine-pyran-dione derivative: DFT enol↔hydrazone tautomerization via zwitterionic intermediate, hirshfeld analysis and optical activity studies

Guerraoui, Abdenour; Djedouani, Amel; Jeanneau, Erwann; Boumaza, A.; Alsalme, Ali; Zarrouk, A.; Salih, Kifah S. M.; Warad, Ismail

doi:10.1016/j.molstruc.2020.128728

Cited by 20 publications

(8 citation statements)

References 32 publications

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“…The calculated C–O bond lengths of reactants and products are in good agreement with the earlier reported length of 1.23 Å [ 50 , 51 ]. A similar pattern was observed for N–N bond lengths (N(14)-N(16) (~1.36 Å)) in both L1 and L2 [ 50 , 52 , 53 ]. The N-N bond length (N(14)-N(16) 1.41 Å) of the unsubstituted thio-semicarbazides is suggestive of some double-bond character [ 52 , 53 ].…”

Section: Resultssupporting

confidence: 77%

“…A similar pattern was observed for N–N bond lengths (N(14)-N(16) (~1.36 Å)) in both L1 and L2 [ 50 , 52 , 53 ]. The N-N bond length (N(14)-N(16) 1.41 Å) of the unsubstituted thio-semicarbazides is suggestive of some double-bond character [ 52 , 53 ]. This can be attributed to the presence of terminal aromatic rings, e.g., thiophene, pyrrole attached to the azomethine nitrogen [ 52 , 53 ].…”

Section: Resultssupporting

confidence: 77%

“…The N-N bond length (N(14)-N(16) 1.41 Å) of the unsubstituted thio-semicarbazides is suggestive of some double-bond character [ 52 , 53 ]. This can be attributed to the presence of terminal aromatic rings, e.g., thiophene, pyrrole attached to the azomethine nitrogen [ 52 , 53 ]. As reported earlier, the C-S single bond distance is 1.82 Å [ 52 ] while the double bond is 1.68 Å [ 54 ].…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

et al. 2022

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Polytopic organic ligands with hydrazone moiety are at the forefront of new drug research among many others due to their unique and versatile functionality and ease of strategic ligand design. Quantum chemical calculations of these polyfunctional ligands can be carried out in silico to determine the thermodynamic parameters. In this study two new tritopic dihydrazide ligands, N’2, N’6-bis[(1E)-1-(thiophen-2-yl) ethylidene] pyridine-2, 6-dicarbohydrazide (L1) and N’2, N’6-bis[(1E)-1-(1H-pyrrol-2-yl) ethylidene] pyridine-2, 6-dicarbohydrazide (L2) were successfully prepared by the condensation reaction of pyridine-2, 6-dicarboxylic hydrazide with 2-acetylthiophene and 2-acetylpyrrole. The FT-IR, 1H, and 13C NMR, as well as mass spectra of both L1 and L2, were recorded and analyzed. Quantum chemical calculations were performed at the DFT/B3LYP/cc-pvdz/6-311+ G (d, p) level of theory to study the molecular geometry, vibrational frequencies, and thermodynamic properties including changes of ∆H, ∆S, and ∆G for both the ligands. The optimized vibrational frequency and (1H and 13C) NMR obtained by B3LYP/cc-pvdz/6-311 + G (d, p) showed good agreement with experimental FT-IR and NMR data. Frontier molecular orbital (FMO) calculations were also conducted to find the HOMO, LUMO, and HOMO–LUMO gaps of the two synthesized compounds. To investigate the biological activities of the ligands, L1 and L2 were tested using in vitro bioassays against some Gram-negative and Gram-positive bacteria and fungus strains. In addition, molecular docking was used to study the molecular behavior of L1 and L2 against tyrosinase from Bacillus megaterium. The outcomes revealed that both L1 and L2 can suppress microbial growth of bacteria and fungi with variable potency. The antibacterial activity results demonstrated the compound L2 to be potentially effective against Bacillus megaterium with inhibition zones of 12 mm while the molecular docking study showed the binding energies for L1 and L2 to be −7.7 and −8.8 kcal mol−1, respectively, with tyrosinase from Bacillus megaterium.‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬

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Section: Resultssupporting

confidence: 77%

Section: Resultssupporting

confidence: 77%

Section: Resultsmentioning

confidence: 99%

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Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

et al. 2022

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“…The experimental spectrum of 3-Cl BHB showed two absorption bands, one located at λ max = 299 nm and the other at λ max = 392 nm, which may be attributed to π → π ∗ transition due to a conjugation in an unsaturated system and n → π ∗ excitation of the conjugation between the lone pair of electrons (N) and the others conjugated bond in 3-Cl BHB, respectively [50] . The absence of visible region absorption and the diversity of absorption peaks in the UV band ensure that the material is suitable for optical and photonic applications [51] . Conversely, the calculated spectrum founded through TD-SCF CAM-B3LYP/6-31G (d,p) method for 3-Cl BHB compound showed a good resemblances in the shape and the band positions with the experimental UV-Vis spectrum in DMSO solvent.…”

Section: Resultsmentioning

confidence: 99%

New bis hydrazone: Synthesis, X-ray crystal structure, DFT computations, conformational study and in silico study of the inhibition activity of SARS-CoV-2

Tabbiche

Bouchama

Chafai

et al. 2022

Journal of Molecular Structure

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“…Hydrazones are important compounds which possess remarkable properties such as degree of rigidity, conjugated system and structural versatility. These hydrazone compounds are widely used in organic synthesis, analytical chemistry and medicine (Thota et al, 2018;Kumar & Narasimhan, 2013;Makhlouf et al, 2020;Guerraoui et al, 2020). Aldehydes/ ketones and hydrazines are used to fabricate hydrazine derivative compounds in organic solvents by various methods utilizing acidic catalysts (glacial acetic acid, hydrochloric acid, sulfuric acid) and basic catalysts (trimethylamine or pyridine) (Pandeya et al, 2003;Somani et al, 2010;Loncle et al, 2004).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal growth, characterization and DFT investigation of a nonlinear optically active cuminaldehyde derivative hydrazone

Meenatchi

Siva²,

Meenakshisundaram

et al. 2021

Acta Crystallogr B Struct Sci Cryst Eng Mater

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Single crystals of (E)-N′-(4-isopropylbenzylidene)isonicotinohydrazide monohydrate (IBIHM) were grown from ethanol by the slow evaporation from solution growth technique at room temperature. The structure was elucidated by single-crystal X-ray diffraction analysis and crystallized in the orthorhombic system with noncentrosymmetric space group P212121. Optical studies reveal that the absorption was minimum in the visible region and the band-gap energy was estimated using the Kubelka–Munk algorithm. The functional groups were identified by Fourier transform infrared spectral analysis. A scanning electron microscopy study revealed the surface morphology of the grown crystal. Investigation of the intermolecular interactions, crystal packing using Hirshfeld surface analysis and single-crystal X-ray diffraction confirm that the close contacts were associated with molecular interactions. Fingerprint plots of Hirshfeld surfaces are used to locate and analyze the percentage of hydrogen-bonding interactions. The second-harmonic generation efficiency of the grown specimen was superior to that of the reference material, potassium dihydrogen phosphate. The grown crystals were further characterized by mass spectrometry and elemental analysis. Theoretical studies using density functional theory (DFT) greatly substantiated the experimental observations. Large first-order molecular hyperpolarizability (β) of about ∼70× was observed for IBIHM. The efficiency of IBIHM in terms of nonlinear optical response was verified and the molecule displayed greater chemical stability and reactivity.

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Crystal structure and spectral of new hydrazine-pyran-dione derivative: DFT enol↔hydrazone tautomerization via zwitterionic intermediate, hirshfeld analysis and optical activity studies

Cited by 20 publications

References 32 publications

Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

New bis hydrazone: Synthesis, X-ray crystal structure, DFT computations, conformational study and in silico study of the inhibition activity of SARS-CoV-2

Synthesis, crystal growth, characterization and DFT investigation of a nonlinear optically active cuminaldehyde derivative hydrazone

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