X-Ray Diffraction and Theoretical Approach to the Molecular Structure of (E)-2-(2-(1,3-dioxoisoindolin-2-yl)-1-(3-phenyl-3-methylcyclobutyl)ethylidene) hydrazine carboxamide

Yilmaz, Betul; Saraçoğlu, Hanife; Çalışkan, Nezihe; Yılmaz, İbrahim; Çukurovalı, Alaaddin

doi:10.1007/s10870-012-0333-6

Cited by 10 publications

(4 citation statements)

References 21 publications

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“…For bond angles, the root mean square error is found 1.361˚ and 1.232˚ for RHF and B3LYP respectively. The correlation coefficient in bond angles by RHF and B3LYP are 0.8966 and 0.9157 respectively, which reveals that the correlation coefficient for bond angles obtained by RHF method are smaller than those determined by B3LYP method as observed in reported research paper [20].…”

Section: Ab-initio and Dft Studiesmentioning

confidence: 54%

Synthesis, Spectroscopic Investigations, Quantum Chemical Studies (<i>Ab-initio</i> & DFT) and Antimicrobial Activities of 3-(3-Chloro-4,5-dimethoxy-phenyl)-1-(4, 5-dimethoxy-2-methyl-Phenyl) prop-2-en-1-one

Patel¹,

Gandhi²,

Barot³

et al. 2013

CSTA

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The chalcones (1,3-diaryl-2-propenones) and their derivatives are important intermediates in organic synthesis and have widespread applications in medicinal industry. The title choloro chalcone derivative, 3-(3-chloro-4,5-dimethoxyphenyl)-1-(4,5-dimethoxy-2-methyl phenyl) prop-2-en-1-one, has been synthesized. It is characterized by FTIR, 1 H NMR, 13 C NMR and single crystal X-ray diffraction. Title compound crystallizes in monoclinic space group C2/c with a = 23.540(11) Å, b = 9.738(4) Å, c = 17.305(7) Å, β = 106.37 (3)˚, V = 3806(3) Å 3 and Z = 8. The mean plane of the two substituted benzene rings is twisted by 66.29 (12)˚ with respect to each other. Ab-initio and density functional Theory (DFT) calculations have been carried out for the title molecule using RHF/6-311G and B3LYP/6-311G basis set respectively. The calculated results show that the predicted geometry can well reproduce structural parameters. In addition, frontier molecular orbitals and Mullikan charge distributions are carried out by using RHF and B3LYP methods. The calculated HOMO and LUMO energies show that charge transfer occurs in the molecule. Numbers of weak but significant interactions like C-H···O, C-H···π and π-π are involved in the stability of the structure. The weak π-π stacked interaction involves the centroids of the methyl phenyl rings with Cg-Cg separation distance of 3.857(2) Å. Synthesized compound has been screened for its antimicrobial activity against different panels of organisms.

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Section: Ab-initio and Dft Studiesmentioning

confidence: 54%

Synthesis, Spectroscopic Investigations, Quantum Chemical Studies (<i>Ab-initio</i> & DFT) and Antimicrobial Activities of 3-(3-Chloro-4,5-dimethoxy-phenyl)-1-(4, 5-dimethoxy-2-methyl-Phenyl) prop-2-en-1-one

Patel¹,

Gandhi²,

Barot³

et al. 2013

CSTA

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“…), respectively. Yılmaz et al . reported values of 1.215 (6)/1.188/1.214 Å for O1‐C1 bond length, 1.383 (6)/1.387/1.405 Å for N4‐C1 one, 1.214 (7)/1.188/1.214 Å for O2‐C8 one, 1.385 (6)/1.386/1.404 Å for N4‐C8 one, 1.487 (7)/1.492/1.494 Å for C1‐C2 one and 1.471 (8)/1.492/1.493 Å for C7‐C8 one (exp./HF/6‐31G(d) level/B3LYP/6‐31G(d) level) in 1,3‐dioxoisoindolin‐2‐yl group of (E)‐2‐(2‐(1,3‐dioxoisoindolin‐2‐yl)‐1‐(3‐phenyl‐3‐methylcyclobutyl)ethylidene) hydrazine carboxamide compound.…”

Section: Resultsmentioning

confidence: 99%

4‐[(1, 3‐Dioxoisoindolin‐2‐yl)methyl]benzenesulfonamide: Full Structural and Spectroscopic Characterization and Molecular Docking with Carbonic Anhydrase II

et al. 2018

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The structural, spectral, electronic, thermodynamic and nonlinear optical features of 4-[(1, 3-dioxoisoindolin-2-yl)methyl] benzenesulfonamide were investigated using experimental and theoretical methods. Experimental characterization was carried out via FT-IR, Raman, carbon-13 and proton NMR chemical shifts and UV-Vis. spectroscopic techniques. The molecular electronic structure computations were done with DFT/B3LYP method using the 6-311 + + G(2d,2p) basis set. VEDA4 software was used to analyze in PED (potential energy distribution) to vibrational profile of computed harmonic frequencies.Hirshfeld surface analysis was performed to determine interactions in crystal packing of the compound. Additionally, the highest occupied molecular orbitals (HOMOs), lowest unoccu-pied molecular orbitals (LUMOs), nonlinear optical (NLO) analysis, molecular electrostatic potential (MEP and ESP) surfaces and thermochemical properties were studied with theoretical computational method. The localization contributions on the defined molecular groups of molecular orbitals in the electronic transitions were investigated. Enzyme-ligand interactions of 4-[(1, 3-dioxoisoindolin-2-yl)methyl]benzenesulfonamide with carbonic anhydrase II were investigated by molecular docking analysis. The experimental and calculated structural and spectroscopic data were compared with each other. The correlation between computed results and experimental records is in a good harmony. Computational proceduresThe structural optimization, vibrational frequencies, 1 H and 13 C NMR chemical shifts, UV-Vis. spectroscopic analysis, HOMO-LUMO studies, molecular electrostatic potential (MEP, ESP and MEP contour) mapping, nonlinear optical features and thermochemical features of the title molecule were investigated with B3LYP functional [12,13] in DFT method at the 6-311 + + G(2d,2p) [a] Dr.

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“…Selected bond lengths and bond angles compared with those of the experimental data are presented in Table 2. [46] The root means square deviation (RMSD) in bond lengths and angles by B3LYP are 0.9891 and 0.9717, respectively. The highest bond length difference is 0.056 Å for the S1-C4 bond, whereas the biggest bond angle deviation occurred in the O1-S1-C4 angle (6.012°) in the B3LYP method.…”

Section: Dft Studiesmentioning

confidence: 99%

“…The observed differences between optimized geometry with those of X-ray data are owing to thermal motion of the atoms, and also due to adopting atomic scattering factors for the spherical (isolated) atom in the X-ray refinement. [46] The root means square deviation (RMSD) in bond lengths and angles by B3LYP are 0.9891 and 0.9717, respectively.…”

Section: Dft Studiesmentioning

confidence: 99%

DNA interaction, cytotoxicity and molecular structure of cobalt complex of 4‐amino‐N‐(6‐chloropyridazin‐3‐yl)benzene sulfonamide in the presence of secondary ligand pyridine

Pandya

Patel

Chaudhary

et al. 2019

Applied Organom Chemis

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Novel cobalt complex of 4-amino-N-(6-chloropyridazin-3-yl)benzene sulfonamide (sulfachloropyridazine) has been synthesized and characterized by elemental analysis, FT-IR spectroscopy and magnetic susceptibility (VSM).Cobalt complex of Sulfachloropyridazine (Co-SCP) crystallized in monoclinic space group P2 1 /n with Z = 4. The structure is solved by direct method and refined to R = 0.099 for 4720 reflections with I ⩾4σ(I). The results of FT-IR spectra suggest the binding of cobalt atom to the sulfonamide ligand which is in agreement with the crystal structure determination. In crystal structure, molecule is linked via, C-H … π, C-Cl … π and π … π intermolecular interactions. The computational studies like the optimization energy and root means square deviation compare with single crystal structure, frontier molecular orbital (Homo-Lumo energy) and binding energy of the Co-SCP has been carried out using DFT/B3LYP level of theory in gaseous phase. Hirshfeld surfaces and the 2D-fingerprint analysis are performed to study the nature of interactions and their measurable contributions towards crystal packing. The interaction of the complex with DNA is investigated using viscosity measurement and absorption titration studies. The result shows the complex bind to DNA with intercalative mode with high DNA-binding constant (K b ). Also, in vivo and in vitro cytotoxic studies are performed using S. pombe cells and brine shrimp lethality bioassay. DNA-cleavage study shows better cleaving ability of the complex.

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X-Ray Diffraction and Theoretical Approach to the Molecular Structure of (E)-2-(2-(1,3-dioxoisoindolin-2-yl)-1-(3-phenyl-3-methylcyclobutyl)ethylidene) hydrazine carboxamide

Cited by 10 publications

References 21 publications

Synthesis, Spectroscopic Investigations, Quantum Chemical Studies (<i>Ab-initio</i> & DFT) and Antimicrobial Activities of 3-(3-Chloro-4,5-dimethoxy-phenyl)-1-(4, 5-dimethoxy-2-methyl-Phenyl) prop-2-en-1-one

Synthesis, Spectroscopic Investigations, Quantum Chemical Studies (<i>Ab-initio</i> & DFT) and Antimicrobial Activities of 3-(3-Chloro-4,5-dimethoxy-phenyl)-1-(4, 5-dimethoxy-2-methyl-Phenyl) prop-2-en-1-one

4‐[(1, 3‐Dioxoisoindolin‐2‐yl)methyl]benzenesulfonamide: Full Structural and Spectroscopic Characterization and Molecular Docking with Carbonic Anhydrase II

DNA interaction, cytotoxicity and molecular structure of cobalt complex of 4‐amino‐N‐(6‐chloropyridazin‐3‐yl)benzene sulfonamide in the presence of secondary ligand pyridine

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X-Ray Diffraction and Theoretical Approach to the Molecular Structure of (E)-2-(2-(1,3-dioxoisoindolin-2-yl)-1-(3-phenyl-3-methylcyclobutyl)ethylidene) hydrazine carboxamide

Cited by 10 publications

References 21 publications

Synthesis, Spectroscopic Investigations, Quantum Chemical Studies (&lt;i&gt;Ab-initio&lt;/i&gt; &amp; DFT) and Antimicrobial Activities of 3-(3-Chloro-4,5-dimethoxy-phenyl)-1-(4, 5-dimethoxy-2-methyl-Phenyl) prop-2-en-1-one

Synthesis, Spectroscopic Investigations, Quantum Chemical Studies (&lt;i&gt;Ab-initio&lt;/i&gt; &amp; DFT) and Antimicrobial Activities of 3-(3-Chloro-4,5-dimethoxy-phenyl)-1-(4, 5-dimethoxy-2-methyl-Phenyl) prop-2-en-1-one

4‐[(1, 3‐Dioxoisoindolin‐2‐yl)methyl]benzenesulfonamide: Full Structural and Spectroscopic Characterization and Molecular Docking with Carbonic Anhydrase II

DNA interaction, cytotoxicity and molecular structure of cobalt complex of 4‐amino‐N‐(6‐chloropyridazin‐3‐yl)benzene sulfonamide in the presence of secondary ligand pyridine

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Product

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Synthesis, Spectroscopic Investigations, Quantum Chemical Studies (<i>Ab-initio</i> & DFT) and Antimicrobial Activities of 3-(3-Chloro-4,5-dimethoxy-phenyl)-1-(4, 5-dimethoxy-2-methyl-Phenyl) prop-2-en-1-one

Synthesis, Spectroscopic Investigations, Quantum Chemical Studies (<i>Ab-initio</i> & DFT) and Antimicrobial Activities of 3-(3-Chloro-4,5-dimethoxy-phenyl)-1-(4, 5-dimethoxy-2-methyl-Phenyl) prop-2-en-1-one