Raman, infrared and DFT studies of N′-(adamantan-2-ylidene)benzohydrazide, a potential antibacterial agent

Shundalau, M. B.; Al‐Abdullah, Ebtehal S.; Shabunya-Klyachkovskaya, E. V.; Hlinisty, A.V.; Al‐Deeb, Omar A.; El-Emam, Ali A.; Гапоненко, С. В.

doi:10.1016/j.molstruc.2016.02.092

Cited by 22 publications

(6 citation statements)

References 32 publications

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“…Such errors are supposed to be connected with the presence of heteroatoms in structure and have already occurred earlier and been discussed. 25,27,28 Planar angles follow the same pattern: deviations of calculated angles from experimental ones are not more than 1%. For planar angles, which include nitrogen and oxygen atoms, an error not exceeding 4.6% is observed.…”

Section: Geometric Structurementioning

confidence: 55%

“…21 On the other hand, 1,2,4-triazole derivatives were reported to exhibit diverse biological activities including antifungal, 22 anti-in°ammatory 23 and anticancer activities. 24 In continuation of our ongoing interest in the pharmacological and structural properties of adamantane derivatives, [25][26][27][28] on the basis of experimental (infrared (IR), Raman and Ultraviolet (UV)/Vis spectroscopy) and theoretical (Density Functional Theory (DFT), Time-Dependent Density Functional Theory (TDDFT) and Multi-Reference Perturbation Theory (MRPT) calculations) methods, we report herein the geometric, electronic and spectral characteristics of the title adamantanetriazole hybrid derivative.…”

Section: Introductionmentioning

confidence: 99%

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Spectral and quantum chemical analysis of ethyl 4-[3-(adamantan-1-yl)-4-phenyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazole-1-yl]methylpiperazine-1-carboxylate

Al-Ghulikah

Meniailava

Vysotskaya

et al. 2019

J. Theor. Comput. Chem.

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The Fourier transform infrared and Raman spectra of the adamantane-based compound ethyl 4-[3-(adamantan-1-yl)-4-phenyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl]methylpiperazine-1-carboxylate were recorded in the ranges of 3200–650[Formula: see text]cm[Formula: see text] and 3200–150[Formula: see text]cm[Formula: see text], respectively. The UV/Vis spectrum of solution of the title compound in ethanol was measured in the range of 450–200[Formula: see text]nm. The DFT calculations at the B3LYP/cc-pVDZ and B3LYP/cc-pVTZ levels of the theory were performed to obtain the equilibrium geometric structure and to predict vibrational IR and Raman spectra of the title molecule. The TDDFT calculations at the CAM-B3LYP/cc-pVTZ level of the theory, as well as MRPT calculations at the CASSCF(4,5)/XMCQDPT2 level of the theory were carried out to reproduce the electronic absorption spectrum. The experimental IR, Raman and UV/Vis spectra were interpreted on the basis of results of quantum chemical modeling. Based on Mulliken and Löwdin atomic population analysis, it was established that the compound under study exhibits features of an intramolecular charge transfer.

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Section: Geometric Structurementioning

confidence: 55%

Section: Introductionmentioning

confidence: 99%

Spectral and quantum chemical analysis of ethyl 4-[3-(adamantan-1-yl)-4-phenyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazole-1-yl]methylpiperazine-1-carboxylate

Al-Ghulikah

Meniailava

Vysotskaya

et al. 2019

J. Theor. Comput. Chem.

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“…Frequencies of CH-and CH 2 -stretching vibrations in monosubstituted adamantyl lay in the range 2952-2850 cm -1 [44]. According to the literature [44] and our calculations [20,22], bands at 2943, 2934, 2911, 2907, 2888, and 2953 cm -1 in the IR spectrum and lines at 2941, 2917, 2909, 2889, 2855, and 2847 cm -1 in the Raman spectrum belonged to adamantyl CH and CH 2 stretching vibrations. Adamantyl CH 2 scissoring vibrations were located at 1475-1440 cm -1 [44].…”

mentioning

confidence: 50%

Spectral Analysis of 3-(Adamantan-1-yl)-4-Ethyl-1-[(4-Phenylpiperazin-1-yl) Methyl]-1H-1,2,4-Triazole-5(4H)-Thione

et al. 2018

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Vibrational IR (3200-650 cm -1 ) and Raman spectra (3200-150 cm -1 ) of adamantane-containing 3- (adamantan-1-yl)-4-ethyl-1-[(4-phenylpiperazin-1-yl)methyl]-1H-1,2,4-triazole-5(4H)-thione, which is promising for drug design, were examined. The UV/Vis spectrum (450-200 nm) of the compound in EtOH was measured. Full geometry optimization using density functional theory (DFT) in the B3LYP/cc-pVDZ approximation allowed the equilibrium confi guration of the molecule to be determined and IR and Raman spectra to be calculated. Based on these, the experimental vibrational IR and Raman spectra were interpreted and the biological activity indices were predicted. The UV/Vis spectrum of the title compound was simulated at the time-dependent DFT/CAM-B3LYP/cc-pVDZ level with and without solvent effects and at the ab initio multi-reference perturbation theory XMCQDPT2 level. The UV/Vis spectrum that was simulated using the multi-reference XMCQDPT2 approximation agreed very successfully with the experimental data, in contrast to the single-reference DFT method. This was probably a consequence of intramolecular charge transfer.

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“…The ambient refractive index higher than 1.5 for continuous media is feasible with many polymers. The polymers can also be added on top of metal particles deposited on various substrates including those with high refractive index (e.g., Si, Ge, CdTe, ZnSe) as we recently demonstrated. , A simple estimate of the anti-Stokes/Stokes enhancement for Figure c can be made as follows. A laser wavelength close to 15,000 cm –1 (such as, e.g., 633 nm in He–Ne laser) and a typical Raman shift of 10 3 cm –3 (e.g., CH-bonds in molecules [34]) gives for ω + = 16,000 cm –1 enhancement about 10 3 whereas the same factor for ω – = 14,000 cm –1 measures approx.…”

Section: Results and Discussionmentioning

confidence: 99%

Strong Selective Anti-Stokes Raman Scattering Enhancement in Plasmonics Using Photon Density of States Engineering

2021

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We demonstrate theoretically the possibility to achieve domination of anti-Stokes Raman scattering enhancement over the Stokes one by means of photon local density of states (LDOS) engineering in model plasmonic nanostructures. The theory predicts anti-Stokes over Stokes scattering enhancement domination when both anti-Stokes and Stokes secondary photons energies correspond to the descending long-wave wing of extinction spectra of metal nanoparticles. The photon LDOS effect is proposed as a rationale for anti-Stokes anomalies reported for surface enhanced Raman spectroscopy, and the model of a dimer formed by two nanospheres is found to provide the reasonable agreement with experimental data explaining both promotion and inhibition of anti-Stokes scattering depending on the laser wavelength used. Our consideration means that evaluation of local temperature based on the anti-Stokes/Stokes ratio in Raman scattering for plasmonic structures cannot be performed. The simple models of isolated and coupled spheres and isolated spheroids, though offering strong anti-Stokes/Stokes enhancement asymmetry, do not promise absolute domination of anti-Stokes process versus the Stokes one, which is necessary for laser cooling effects. In a more general context, photon DOS engineering can be purposefully used to highlight anti-Stokes versus Stokes scattering even in the case of inhibited Raman scattering, provided that d(LDOS)/dω ≫ 1 holds, that is, DOS sharply grows with frequency.

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Raman, infrared and DFT studies of N′-(adamantan-2-ylidene)benzohydrazide, a potential antibacterial agent

Cited by 22 publications

References 32 publications

Spectral and quantum chemical analysis of ethyl 4-[3-(adamantan-1-yl)-4-phenyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazole-1-yl]methylpiperazine-1-carboxylate

Spectral and quantum chemical analysis of ethyl 4-[3-(adamantan-1-yl)-4-phenyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazole-1-yl]methylpiperazine-1-carboxylate

Spectral Analysis of 3-(Adamantan-1-yl)-4-Ethyl-1-[(4-Phenylpiperazin-1-yl) Methyl]-1H-1,2,4-Triazole-5(4H)-Thione

Strong Selective Anti-Stokes Raman Scattering Enhancement in Plasmonics Using Photon Density of States Engineering

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