Molecular structure and computational studies on 2-((2-(4-(3-(2,5-dimethylphenyl)-3-methylcyclobutyl)thiazol-2-yl)hydrazono)methyl)phenol monomer and dimer by DFT calculations

Karakurt, Tuncay; Çukurovalı, Alaaddin; Subasi, N. Tuna; Kani, İbrahim

doi:10.1016/j.molstruc.2016.07.009

Cited by 15 publications

(7 citation statements)

References 61 publications

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“…While the O-H group, which does not contain an intramolecular or intermolecular hydrogen bonding, has a free vibration frequency between 3700 and 3550 cm −1 , this vibration frequency containing hydrogen bonding is observed between 3550 and 3200 cm −1 [37]. In our study, this frequency value was observed at 3293 cm −1 , while it was calculated at 3459 cm −1 for HF level and at 3224 cm −1 for B3LYP level and compares well with the value reported previously as 3436 cm −1 for experimentally and 3406 cm −1 for B3LYP level [38]. Experimental and calculated 1 H and 13 C chemical shift values for the title molecule are given comparatively in Table 6.…”

Section: Spectroscopic Studiessupporting

confidence: 91%

“…The chemical shift values of these atoms are higher than other carbon atoms. Due to deshielding by the electronegative property of the N and S atoms, the chemical shift values of C14, C15 and C16 atoms are greater than the other carbon atoms and were experimentally found to be 165.38, 107.61 and 153.3 ppm, respectively which is consistent with the values reported previously (168.54, 99.58 and 151.07 ppm) [38]. Similarly, the C1 and C12 carbon peaks linked to O1 and O2 atoms were experimentally found to be 157.05 and 160.15 ppm.…”

Section: Spectroscopic Studiessupporting

confidence: 90%

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Syntheses, spectral characterization, single crystal X-ray diffraction and computational in gas and solid phases studies on chloro- acetic acid N′-(2- hydroxy-naphthalen- 1-ylmethylene)- N- [4-(3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-hydrazide

2020

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In this study, the molecular structure of single crystal containing Schiff bases has been characterized by X-ray diffraction, NMR, IR and UV-Vis spectral techniques and compared with similar molecules in the literature. For the purpose of supporting X-ray results, geometric parameters and spectroscopic studies of the title compound were theoretically performed by Hartree-Fock and density functional theory methods. In addition, the title compound's molecular energies, Mulliken-ESP-NPA-Hirshfeld charges, molecular electrostatic potential surface, Frontier orbitals and thermodynamic properties to elucidate intermolecular interactions were calculated. All the calculations in gas and solid phases were carried out using Gaussian 09 and Quantum Espresso programs. It was found that the studies of X-ray are more compatible with the calculations made in the solid phase.

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Section: Spectroscopic Studiessupporting

confidence: 91%

Section: Spectroscopic Studiessupporting

confidence: 90%

Syntheses, spectral characterization, single crystal X-ray diffraction and computational in gas and solid phases studies on chloro- acetic acid N′-(2- hydroxy-naphthalen- 1-ylmethylene)- N- [4-(3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-hydrazide

2020

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“…The bond distance between the carbon atoms are 1.556 Å on average and bond angles formed by the three carbons are 88.66° on average. When these values are compared with the previously reported cyclobutane derivatives [21][22][23][24][25][26][27][28][29][38][39][40][41], it can be seen that there are no considerable differences. The dihedral angles between cyclobutane planes are 24.93 (28)° (C10/C11/C13 -C13/C12/C10) and 24.52 (25)° (C11/C10/C12 -C12/C13/C11).…”

Section: Structural Description Of the Title Compoundmentioning

confidence: 95%

Structure determination, vibrational bands and chemical shift assignments of 3-(4-(3-(2,5-dimethylphenyl)-3-methylcyclobutyl)thiazol-2-yl)-2-(o-tolyl)thiazolidin-4-one: A combined experimental and quantum chemical density-functional theory studies

Şen

2019

Maced. J. Chem. Chem. Eng.

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This paper report is an analysis of the title compound by means of X-ray crystallography, FT-IR, NMR and DFT calculations, in the context of structural and spectral characterization. The crystal and molecular structures of the compound were determined by single-crystal X-ray diffraction (SCXRD). Fourier Transform Infrared (FTIR) spectrum was recorded in the range from 400 cm–1 to 4000 cm–1. The 1H and 13C nuclear magnetic resonance (NMR) spectra were also recorded. DFT calculations were employed to support X-ray molecular geometry and calculate IR and NMR (1H and 13C) spectral bands. The structural (bond lengths, bond angles, torsion angles) and spectral (vibrational modes and chemical shifts) parameters obtained from DFT levels (B3LYP/6-31G(d,p) and B3LYP/6-31G+(d,p)) were compared with experimental findings, and an excellent harmony between the two data was ascertained.

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“…Quantum mechanics are also widely used to investigate the molecules at the molecular level to give useful guidelines in the design of organic NLOphoric materials. [17,[45][46][47][48][49][50][51][52][53][54] In the present work, we have investigated for the first time the effect of functional group isomers and position isomers of azo and azomethine, and their effect on linear and non-linear optical properties. For this purpose, we have selected three reported molecules [55,56] VA-1,VI (1-2) and are synthesized as previously reported by our group in same manner we have synthesized one azo analog VA-2 (see Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Linear and NLO Properties of Functional Group and Position Isomers of Azo and Azomethine: Comparative Photophysical‐Electrochemical Properties, Z‐Scan and DFT Studies

Mishra

Ghanavatkar

Sharma³

et al. 2020

ChemistrySelect

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Functional group and position isomers of azo and azomethine were selected to investigate their effect on linear and NLO properties. The azo and azomethine analogs show absorption maxima in the range 460–500 nm and 375–435 nm respectively. They are emissive in green, orange to the deep red region with a large Stokes shift of 100–200 nm. When we compared azo and azomethine chromophores i. e. functional group isomers, azo chromophore shows a bathochromic shift of 50–103 nm, while in case of position isomers azo and azomethine having larger conjugation effect i. e. VA‐2 and VI‐2 show a more bathochromic shift of 28 nm and 42 nm than the corresponding analogs VA‐1 and VI‐1, which show respectively 466 nm and 379 nm. Band gaps evaluated by electrochemical method and DFT method are correlated with the bathochromic shift in absorption maxima. The dyes are thermally stable (up to 280 °C). Open and closed aperture Z‐scan techniques were used to evaluate the third order non‐linear optical (NLO) parameters ‐ nonlinear absorptive coefficient (β), nonlinear refractive index (η2), and third order non‐linear optical susceptibility (χ (3)). NLO properties were theoretically calculated by using DFT method with six different functionals. Mean absolute error (MAE) and standard deviation (SD) were evaluated to get more insight into theoretical calculation. With the set of calculated data points, MAE and SD calculated to check performance of the DFT functional. Different functionals were used to evaluate vertical excitation values and compared it with experimental absorption maxima.

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Molecular structure and computational studies on 2-((2-(4-(3-(2,5-dimethylphenyl)-3-methylcyclobutyl)thiazol-2-yl)hydrazono)methyl)phenol monomer and dimer by DFT calculations

Cited by 15 publications

References 61 publications

Syntheses, spectral characterization, single crystal X-ray diffraction and computational in gas and solid phases studies on chloro- acetic acid N′-(2- hydroxy-naphthalen- 1-ylmethylene)- N- [4-(3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-hydrazide

Syntheses, spectral characterization, single crystal X-ray diffraction and computational in gas and solid phases studies on chloro- acetic acid N′-(2- hydroxy-naphthalen- 1-ylmethylene)- N- [4-(3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-hydrazide

Structure determination, vibrational bands and chemical shift assignments of 3-(4-(3-(2,5-dimethylphenyl)-3-methylcyclobutyl)thiazol-2-yl)-2-(o-tolyl)thiazolidin-4-one: A combined experimental and quantum chemical density-functional theory studies

Linear and NLO Properties of Functional Group and Position Isomers of Azo and Azomethine: Comparative Photophysical‐Electrochemical Properties, Z‐Scan and DFT Studies

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