Structural investigation of (2E)-2-(ethoxycarbonyl)-3-[(4-methoxyphenyl)amino]prop-2-enoic acid: X-ray crystal structure, spectroscopy and DFT

Venkatesan, P.; Rajakannan, V.; Venkataramanan, Natarajan Sathiyamoorthy; Ilangovan, Andivelu; Sundius, Tom; Thamotharan, Subbiah

doi:10.1016/j.molstruc.2016.04.090

Cited by 24 publications

(12 citation statements)

References 25 publications

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“…63 The selection of M06-2X and basis set has been made on our earlier studies. [64][65][66][67][68][69] The vibrational frequency was calculated for the optimized geometry in vacuum and solvent phases to determine the energy minima on the potential energy surface and were found to have no negative frequencies. All the solution phase calculations were carried out by using the conductor-like polarizable continuum model (CPCM).…”

Section: Materials and Instrumentsmentioning

confidence: 99%

Solvatochromism and pH effect on the emission of a triphenylimidazole-phenylacrylonitrile derivative: experimental and DFT studies

et al. 2019

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Section: Materials and Instrumentsmentioning

confidence: 99%

Solvatochromism and pH effect on the emission of a triphenylimidazole-phenylacrylonitrile derivative: experimental and DFT studies

et al. 2019

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“…To quantify the energies associated with various intermolecular interactions present in the crystal structure of I, PIXEL calculation [35][36][37] was carried out as reported earlier. [38][39][40][41] Briefly, the distances involving hydrogen atoms are moved to their neutron values (C−H = 1.089 Å and O−H = 0.993 Å) and the resultant geometry used for the calculation. The electron density of the molecule has been obtained at the MP2/6-31G** level of theory using Gaussian 09.…”

Section: Hirshfeld Surface Analysis Pixel Energy Calculation and Crymentioning

confidence: 99%

“…The choice of M05-2X functional was selected based on the previous reports which were able to predict correct binding energies between molecules with weak interactions. 40,41,47 The interaction energy E int was computed for all six motifs at their crystal structure geometry using the supramolecular approach. The E int was corrected for basis set superposition error (BSSE) using the counterpoise method.…”

Section: Computational Detailsmentioning

confidence: 99%

Quantitative analysis of intermolecular interactions in 2,2’-((4-bromophenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one): insights from crystal structure, PIXEL, Hirshfeld surfaces and QTAIM analysis

et al. 2018

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The crystallographic study of 2,2'-((4-bromophenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1one) reveals that the compound crystallizes in the centrosymmetric space group P2 1 /c. In the solid state, the structure of the title compound exhibits two strong intramolecular O−H • • • O hydrogen bonding interactions. Further, molecules of the title compound are self-assembled by weak intermolecular C−H • • • O, π • • • π and H • • • H and C−H • • • Br contacts. Various intermolecular interaction that exist in the crystal structure and their energetics are quantified using PIXEL, DFT and QTAIM analyses. Six different motifs are identified from the PIXEL calculation. Lattice energy calculation suggests that the dispersion energy has the highest contribution for the crystal formation. The relative contributions of various intermolecular contacts in the title compound and its closely related analogs are evaluated using Hirshfeld surface analysis and the decomposed fingerprint plots. The common packing features exist between the title compound and its related analogs are identified. The quantitative molecular electrostatic potential surface diagram depicts the potential binding sites which are in good agreement with the crystal structure of the title compound. The structures of title compound in gas and solvent phases are compared with the experimental structure and reveals that they are superimposed very well. The vibrational modes of the monomer and four most stabilized dimers are characterized using both the experimental and DFT calculations. The UV-Vis spectrum is calculated using time dependent-DFT (TD-DFT) method and compared with experimental spectrum. The results indicate that the calculated energy of absorbance and oscillator strength correlate well with the experimental data.

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“…Furthermore, the time-dependent DFT calculation was carried out in ethanol solvent at the M052X/6-31+G(d) level theory. The choice of the basis set was made based on our previous studies [19,20]. Figure 4 represents the FTIR spectrum of 4-NBA.…”

Section: Single Crystal Xrd and Ftir Spectroscopic Studiesmentioning

confidence: 99%

Linear and nonlinear optical properties of 4-nitrobenzoic acid (4-NBA) single crystals

et al. 2018

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4-Nitrobenzoic acid (4-NBA) single crystals were studied for their linear and nonlinear optical properties. The crystals were grown by slow solvent evaporation method at room temperature. The structure and functional groups were confirmed by X-ray diffraction (XRD) and Fourier transform infrared (FTIR) spectroscopic studies. The 4-NBA crystal has an optical absorption at 263 nm and a wide transparency window for the visible light. Theoretical predictions for the measured optical absorption and charge transfer mechanism in 4-NBA were explained with HOMO and LUMO illustrations. The crystal is found to be birefringent and has produced an optical quality interference pattern. The optic plane of the crystal is observed along 100 direction. The crystal exhibits nonlinear optical effects viz. reverse saturable absorption and selfdefocussing of laser beam. Considerable nonlinear refraction (n 2) and nonlinear absorption (β) coefficients and third-order nonlinear optical susceptibility (χ (3)) were determined using Z-scan technique.

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Structural investigation of (2E)-2-(ethoxycarbonyl)-3-[(4-methoxyphenyl)amino]prop-2-enoic acid: X-ray crystal structure, spectroscopy and DFT

Cited by 24 publications

References 25 publications

Solvatochromism and pH effect on the emission of a triphenylimidazole-phenylacrylonitrile derivative: experimental and DFT studies

Solvatochromism and pH effect on the emission of a triphenylimidazole-phenylacrylonitrile derivative: experimental and DFT studies

Quantitative analysis of intermolecular interactions in 2,2’-((4-bromophenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one): insights from crystal structure, PIXEL, Hirshfeld surfaces and QTAIM analysis

Linear and nonlinear optical properties of 4-nitrobenzoic acid (4-NBA) single crystals

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