Molecular structure, second- and third-order nonlinear optical properties and DFT studies of a novel non-centrosymmetric chalcone derivative: (2E)-3-(4-fluorophenyl)-1-(4-{[(1E)-(4-fluorophenyl)methylene]amino}phenyl)prop-2-en-1-one

Maidur, Shivaraj R.; Patil, P. S.; Ekbote, Anusha; Chia, Tze Shyang; Quah, Ching Kheng

doi:10.1016/j.saa.2017.05.015

Cited by 85 publications

(16 citation statements)

References 60 publications

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“…We assign carbonyl stretching, vibration in the experimental spectrum at 1656 cm −1 and theoretically at 1650 cm −1 . These values agree with previously reported values of Chalcones derivatives [30,31]. The C-H stretching vibrations of aromatic and vinyl groups were normally seen in the region above 3000 cm −1 [34].…”

Section: Ft-ir Spectrum Analysissupporting

confidence: 92%

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Synthesis, spectroscopic characterization, XRD crystal structure, DFT and antimicrobial study of (2E)-3-(2,6-dichlorophenyl)-1-(4-methoxyphenyl)-prop-2-en-1-one

et al. 2020

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The single crystal of synthesized (2E)-3-(2, 6-dichlorophenyl)-1-(4-methoxyphenyl) prop-2-en-1-one is characterized by FT-IR, UV-visible, 1 H NMR, HRMS techniques. The molecular structure was elucidated by using single-crystal X-ray diffraction technique. The title compound crystallizes in the orthorhombic crystal system of P-2 1 2 1 2 1 space group where the unit cell parameters are a = 6.4704 (4) Å, b = 12.9304 (8) Å, c = 16.7181 (11) Å, α = 90°, β = 90°, γ = 90° and Z = 4. The molecular geometry, vibrational frequencies (FT-IR) of title compound have been calculated using the DFT/(B3LYP) method with 6-311++ G (d, p) basis set and compared with the experimental data which shows good agreement. TD-DFT approach is used to compute the UV-visible spectrum. The HOMO-LUMO energy gap, experimentally (4.1096) and theoretically calculated (4.09096) are nearly same. The chemical reactivity parameters have also been studied. The results obtained from the DFT analysis show good agreement with experimental data. The synthesized compound was also screened for antimicrobial activity and it shows moderate antimicrobial activity.

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Section: Ft-ir Spectrum Analysissupporting

confidence: 92%

“…Experimental sp3 C-O bond length is observed between 1.4246 and 1.3574 Å, calculated ones were detected at 1.367-1.335 Å (B3LYP). The average C-Cl bond lengths of 1.732 Å and found within the expected range all bond lengths and angles are within the normal ranges and compared with previously reported structures of chalcones[29][30][31].…”

supporting

confidence: 80%

Synthesis, spectroscopic characterization, XRD crystal structure, DFT and antimicrobial study of (2E)-3-(2,6-dichlorophenyl)-1-(4-methoxyphenyl)-prop-2-en-1-one

et al. 2020

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“…: 141–143°C (Lit: 156.37°C). [ 36 ] IR (KBr, cm −1 ): 3,043, 2,981, 2,921, 2,878, 1,656, 1,624, 1,581, 1,562, 1,506, 1,414, 1,335, 1,321, 1,291, 1,228, 1,213, 1,159, 1,089, 1,022, 1,008, 987, 889, 830, 815, 783, 672, 649, 535, 512, and 497. 1 H‐NMR (400 MHz, DMSO‐ d 6 ) δ 8.69 (s, 1H), 8.26 (d, J = 8.6 Hz, 2H), 8.09–7.94 (m, 5H), 7.78 (d, J = 15.6 Hz, 1H), 7.47–7.37 (m, 4H), and 7.33 (t, J = 8.9 Hz, 2H).…”

Section: Methodsmentioning

confidence: 99%

“…In this study, we first synthesized 12 new and four known ( 3e , [ 34 ] 5b , [ 35 ] 5d , [ 36 ] and 5e [ 37 ] ) chalcone derivatives containing Schiff bases, which were considered to have a broad biological activity, and performed the characterization of these compounds. To determine the antiepileptic and anticholinergic properties of the synthesized compounds, their inhibitory potentials against carbonic anhydrase I–II isoenzymes and AChE enzymes were investigated in this study.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and biological studies of chalcone derivatives containing Schiff bases: Synthetic derivatives for the treatment of epilepsy and Alzheimer's disease

Koçyiğit

Taslimi

2020

Archiv der Pharmazie

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In this study, first, Schiff base-containing chalcone derivatives were synthesized. The human carbonic anhydrase (hCA) isoenzymes I and II were then purified from human erythrocytes using Sepharose-4B-L-tyrosine-sulfanilamide affinity chromatography. In addition, the inhibitory effects of the newly synthesized compounds on the activities of hCA and acetylcholinesterase (AChE) were investigated in vitro, using the esterase and acetylcholine iodide method. The IC 50 values were determined and the K i values of AChE and hCA activities were calculated from the Lineweaver-Burk graphs determined in this study. The hCA I isoform was inhibited by these chalcone derivatives containing Schiff bases (3a-j and 5a-f) in low nanomolar levels, whose K i values ranged between 141.88 ± 24.10 and 2,234.47 ± 38.11 nM. Against the physiologically dominant isoform hCA II, the compounds demonstrated K i values varying from 199.31 ± 40.45 to 602.79 ± 263.22 nM. Also, these compounds effectively inhibited AChE, with K i values ranging from 20.41 ± 6.04 to 125.94 ± 23.88 nM. According to these results, the newly synthesized molecules were found to be potent inhibitors of these enzymes.

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“…The MEP map provides the useful information regarding the reactive sites, delocalization, charge density, molecular size, shape and more significantly explains the positive, negative and neutral electrostatic potential in connection with different colour grading [17]. It is one of the powerful tools that foretells how the charge transfer interaction and the interaction between various kinds of geometries could take place along with information on electrophilic, nucleophilic reactions and hydrogen bonding interactions.…”

Section: Molecular Electrostatic Potential (Mep)mentioning

confidence: 99%

Evaluation of structural, Hirshfeld surface and density functional theory of novel NLO thienyl chalcone single crystal

et al. 2019

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A novel NLO-active chalcone derivative (E)-1-(5-chlorothiophene-2-yl)-3-(4-dimethylamino) phenyl) prop-2-en-1-one has been synthesized by adopting Claisen-Schmidt condensation reaction method. Using DMF as solvent, single crystals of the compound were grown by solution growth technique. The grown crystals are of diamond-shaped dark red colour in nature, and these crystals are characterized using different experimental methods. NMR and LC-MS spectral methods are used to confirm the molecular structure of the synthesized compound. The observed fluorescence spectrum clearly signifies that the newly grown crystal could be utilized as a new green light-emitting material. The molecular 3-dimensional hirshfeld surface and the corresponding 2-dimensional finger print plot representation quantifying the percentage contribution of each individual atom present in the compound were studied. From the density functional theory, the values of HOMO, LUMO and their energy gap were determined. The values of global chemical reactivity descriptors such as chemical hardness (η), global softness (σ), electrophilicity (ω), ionization potential (I) and chemical potential (μ) have been calculated. The molecular electrostatic potential map identifies the potential sites for electrophilic and nucleophilic attack in the molecule. The NLO parameters such as molecular polarizability (α), dipole moment (μ) and first-order hyperpolarizability (β) were determined using density functional theory.

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Molecular structure, second- and third-order nonlinear optical properties and DFT studies of a novel non-centrosymmetric chalcone derivative: (2E)-3-(4-fluorophenyl)-1-(4-{[(1E)-(4-fluorophenyl)methylene]amino}phenyl)prop-2-en-1-one

Cited by 85 publications

References 60 publications

Synthesis, spectroscopic characterization, XRD crystal structure, DFT and antimicrobial study of (2E)-3-(2,6-dichlorophenyl)-1-(4-methoxyphenyl)-prop-2-en-1-one

Synthesis, spectroscopic characterization, XRD crystal structure, DFT and antimicrobial study of (2E)-3-(2,6-dichlorophenyl)-1-(4-methoxyphenyl)-prop-2-en-1-one

Synthesis, characterization, and biological studies of chalcone derivatives containing Schiff bases: Synthetic derivatives for the treatment of epilepsy and Alzheimer's disease

Evaluation of structural, Hirshfeld surface and density functional theory of novel NLO thienyl chalcone single crystal

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