Synthesis, vibrational, NMR, quantum chemical and structure-activity relation studies of 2-hydroxy-4-methoxyacetophenone

Arjunan, V.; Devi, L. Ganga; Subbalakshmi, R.; Rani, T.; Mohan, S.

doi:10.1016/j.saa.2014.03.121

Cited by 96 publications

(33 citation statements)

References 64 publications

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“…Theoretically, the calculated band at 3155 cm -1 is assigned as υOH mode [25]. The in-plane OH deformation [26] is expected in the region 1400±40 cm -1 , and the band at 1435 cm -1 , as calculated by DFT, is assigned this mode, which is not pure but contains significant contributions from anthraquinone ring-stretching modes. The in-plane and out-of-plane OH bending vibrations are observed at 1419 cm -1 and 860 cm -1 , respectively, in the IR spectrum [25].The stretching mode of the hydroxyl group with respect to the anthraquinone moiety υ(C 3 -O 61 ) h appears at 1257 cm -1 in the Raman spectrum, and the calculated value is 1259 cm -1 .…”

Section: Ir and Raman Spectramentioning

confidence: 86%

Spectroscopic investigation (FT-IR and FT-Raman), vibrational assignments, HOMO–LUMO analysis and molecular docking study of 1-hydroxy-4,5,8-tris(4-methoxyphenyl) anthraquinone

Renjith¹,

Mary

Varghese

et al. 2015

Journal of Physics and Chemistry of Solids

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Section: Ir and Raman Spectramentioning

confidence: 86%

Spectroscopic investigation (FT-IR and FT-Raman), vibrational assignments, HOMO–LUMO analysis and molecular docking study of 1-hydroxy-4,5,8-tris(4-methoxyphenyl) anthraquinone

Renjith¹,

Mary

Varghese

et al. 2015

Journal of Physics and Chemistry of Solids

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“…The negative (red and yellow) regions of MEP were related to electrophilic reactivity and the positive regions (blue) to nucleophilic reactivity. In fact, a large HOMO-LUMO energy gap implies high molecular stability in the sense of its lower reactivity in different chemical reactions [56,57]. From the MEP it is evident that the negative charge covers the C=O and C=S groups and the positive region is over the hydrogen of the furan ring and over the hydrogen corresponding to the aromatic rings.…”

Section: Computational Detailsmentioning

confidence: 99%

Structural, vibrational and electronic characterization of 1-benzyl-3-furoyl-1-phenylthiourea: an experimental and theoretical study

et al. 2015

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1-benzyl-3-furoyl-1-phenylthiourea is a thiourea derivative synthesized and characterized by means of vibrational spectroscopy (IR and Raman) multinuclear NMR ( 1 H and 13 C) and elemental analysis. The geometrical parameters of this compound obtained from XRD studies were compared with the calculated values [B3LYP/6-311++G(d,p)] showing a good agreement. As determined by XRD analysis performed previously, the title compound exhibits the U-shape conformation with the C=O and C=S double bonds in anticlinal geometry. This conformational feature is mainly dictated by the substitution degree on the thiourea core and the ability of forming and intramolecular N-H···O=C hydrogen bond. The UV-visible absorption spectra of the compound in methanol solution were recorded and analyzed using time dependent density functional theory (TD-DFT). Molecular stability was investigated by applying the natural bond (NBO) analysis. Intermolecular interactions were evaluated by means of AIM approach. The calculated HOMO and LUMO energies show that the charge transfer occurs in the molecule. The molecular electrostatic potential map was calculated by DFT method. Non-linear optical (NLO) behavior of the title compound was investigated by determining of electric dipole moment, polarizability α, and hyperpolarizability β using B3LYP/6-311++G(d,p) approximation.

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“…Furthermore, a large HOMO‐LUMO gap indicates a high molecular stability in the sense of its lower reactivity in chemical reactions …”

Section: Resultsmentioning

confidence: 93%

Theoretical and experimental investigations of complexation with BF₃.Et₂O effects on electronic structures, energies and photophysical properties of Anil and tetraphenyl (hydroxyl) imidazol

Chaabéne

Agren

Allouche

et al. 2019

Applied Organom Chemis

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The novel compounds (E)-2-(((4-hydroxyphenyl)imino)methyl)phenol, Tetraphenyl (hydroxyl) imidazole and their corresponding Boron difluoride complexes were synthesized and characterized by spectroscopic techniques.Density functional theory calculations at B3LYP-D3/6-311++G (d, p) level of theory were performed for the geometric parameters. The MEP surface studies were used to understand the behavior of molecules in terms of charge transfer and to determine how these molecules interact. We used the GIAO and the B3LYP-D3 with a 6-311++ G (d, p) basis set to simulate the ( 1 H-NMR and 19 F-NMR) and the IR spectra, respectively. The corresponding calculated results are in good agreement with the experimental data. The stability of the molecule arising from hyperconjugation interaction and charge delocalization were analyzed using NBO analysis. FMOs revealed the occurrence of charge transfer within the molecule. The complexation using BF 3 .Et 2 O was also found to have remarkable effects on the electrochemical properties of the studied molecules, where (b) and (d) present lower chemical stability, higher reactivity and higher polarizability than (a) and (c), respectively. Moreover, the energy gap of (a) and (c) decreased after complexation using BF 3 .Et 2 O, indicating the reliability of the electrochemical evaluation of LUMO and HOMO energy levels. These values are the factors explaining the possible charge transfer interaction within the molecule. The absorption and emission spectra of the model compound were also simulated and compared to experimental observations in the DMF solvent. The results of DFT calculations supported the structural and spectroscopic data and confirmed the structure modification of frontier molecular orbitals for BF 2 complexes as well as tunable potentials and energy levels.

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Synthesis, vibrational, NMR, quantum chemical and structure-activity relation studies of 2-hydroxy-4-methoxyacetophenone

Cited by 96 publications

References 64 publications

Spectroscopic investigation (FT-IR and FT-Raman), vibrational assignments, HOMO–LUMO analysis and molecular docking study of 1-hydroxy-4,5,8-tris(4-methoxyphenyl) anthraquinone

Spectroscopic investigation (FT-IR and FT-Raman), vibrational assignments, HOMO–LUMO analysis and molecular docking study of 1-hydroxy-4,5,8-tris(4-methoxyphenyl) anthraquinone

Structural, vibrational and electronic characterization of 1-benzyl-3-furoyl-1-phenylthiourea: an experimental and theoretical study

Theoretical and experimental investigations of complexation with BF₃.Et₂O effects on electronic structures, energies and photophysical properties of Anil and tetraphenyl (hydroxyl) imidazol

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Synthesis, vibrational, NMR, quantum chemical and structure-activity relation studies of 2-hydroxy-4-methoxyacetophenone

Cited by 96 publications

References 64 publications

Spectroscopic investigation (FT-IR and FT-Raman), vibrational assignments, HOMO–LUMO analysis and molecular docking study of 1-hydroxy-4,5,8-tris(4-methoxyphenyl) anthraquinone

Spectroscopic investigation (FT-IR and FT-Raman), vibrational assignments, HOMO–LUMO analysis and molecular docking study of 1-hydroxy-4,5,8-tris(4-methoxyphenyl) anthraquinone

Structural, vibrational and electronic characterization of 1-benzyl-3-furoyl-1-phenylthiourea: an experimental and theoretical study

Theoretical and experimental investigations of complexation with BF3.Et2O effects on electronic structures, energies and photophysical properties of Anil and tetraphenyl (hydroxyl) imidazol

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Theoretical and experimental investigations of complexation with BF₃.Et₂O effects on electronic structures, energies and photophysical properties of Anil and tetraphenyl (hydroxyl) imidazol