Quantum Computational Investigation of (E)-1-(4-methoxyphenyl)-5-methyl-N′-(3-phenoxybenzylidene)-1H-1,2,3-triazole-4-carbohydrazide

Gökçe, Halil; Şen, Fatih; Sert, Yusuf; Abdel‐Wahab, Bakr F.; Kariuki, Benson M.; El‐Hiti, Gamal A.

doi:10.3390/molecules27072193

Cited by 73 publications

(10 citation statements)

References 72 publications

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“…A residual band at 2090 cm −1 is nevertheless still present for Copo3, indicating an incomplete Cr–salen addition. However, in each case, a peak at 1538 cm −1 appears clearly, characteristic of a triazole-cycle deformation mode [ 31 ]. A new peak at 1622 cm −1 is, moreover, visible, which can be attributed to the υC = N stretching vibration of the salen complex [ 14 ].…”

Section: Resultsmentioning

confidence: 99%

Post-Modification of Copolymers Obtained by ATRP for an Application in Heterogeneous Asymmetric Salen Catalysis

et al. 2022

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Copolymers are valuable supports for obtaining heterogeneous catalysts that allow their recycling and therefore substantial savings, particularly in the field of asymmetric catalysis. This contribution reports the use of two comonomers: Azido-3-propylmethacrylate (AZMA) bearing a reactive azide function was associated with 2-methoxyethyl methacrylate (MEMA), used as a spacer, for the ATRP synthesis of copolymers, and then post-functionalized with a propargyl chromium salen complex. The controlled homopolymerization of MEMA by ATRP was firstly described and proved to be more controlled in molar mass than that of AZMA for conversions up to 63%. The ATRP copolymerization of both monomers made it possible to control the molar masses and the composition, with nevertheless a slight increase in the dispersity (from 1.05 to 1.3) when the incorporation ratio of AZMA increased from 10 to 50 mol%. These copolymers were post-functionalized with chromium salen units by click chemistry and their activity was evaluated in the asymmetric ring opening of cyclohexene oxide with trimethylsilyl azide. At an equal catalytic ratio, a significant increase in enantioselectivity was obtained by using the copolymer containing the largest part of salen units, probably allowing, in this case, the more favorable bimetallic activation of both the engaged nucleophile and electrophile. Moreover, the catalytic polymer was recovered by simple filtration and re-engaged in subsequent catalytic runs, up to seven times, without loss of activity or selectivity.

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Section: Resultsmentioning

confidence: 99%

Post-Modification of Copolymers Obtained by ATRP for an Application in Heterogeneous Asymmetric Salen Catalysis

et al. 2022

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“…Materials that exhibit good NLO property are applied in the construction of light emitting diode (LED), optical memory, frequency switching devices, and biosensors. [ 38,39 ] Herein, NLO property of the investigated compounds were estimated at DFT/B3LYP/6‐311+G(d,p) theory level. First order hyperpolarizability (β total ) which is the primary factor that tells if a particular material reflects good NLO property for optoelectronic application, in conjunction with total dipole moment (μ), linear polarizability (α total ) and anisotropy of the polarizability (∆ α ) of the compounds under study was evaluated with the aid of the following equations.

β_{x} goodbreak= β_{xxx} goodbreak+ β_{xyy} goodbreak+ β_{xzz}

β_{y} goodbreak= β_{yyy} goodbreak+ β_{xxy} goodbreak+ β_{yzz}

β_{z} goodbreak= β_{zzz} goodbreak+ β_{xxz} goodbreak+ β_{yyz}

β_{total} goodbreak= \sqrt{(β_{x}^{2} + β_{y}^{2} + β_{z}^{2})}

μ goodbreak= \sqrt{(μ_{x}^{2} + μ_{y}^{2} + μ_{z}^{2})}

α_{total} goodbreak= \frac{(\propto_{italicxx} + \propto_{italicyy} + \propto_{italiczz})}{3}

∆...

…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization, DFT studies, and molecular modeling of hydrazinelidene‐3‐oxo‐3‐(p‐olyl) propanal derivatives as potential candidate for Hepatitis B and C treatment

Louis,

Egemonye,

Edet

et al. 2022

Vietnam Journal of Chemistry

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Serious liver conditions including cirrhosis, hepatocellular carcinoma, and liver failure can be brought on by hepatitis B and C (HBV and HCV) infection. In our study, compound H_B and H_E were synthesized, spectroscopically, theoretically characterized, and investigated as potential drug for HBV and HCV. The stability of the investigated compounds as well as their Inter‐ and intramolecular interactions were investigated using the density functional theory with the B3LYP/6‐311+G (d, p) basis set. Lower energy gaps for studied compounds indicate compound ds to be reactive. The maximal absorption wavelengths of the substances under investigation were ascertained using the UV absorption spectrum. The optical property of the compounds under investigation was also calculated. Various vibrational modes displayed by functional groups present in the examined compounds were considered. Thereafter, docking was performed to determine the compatibility of compounds in study with selected hepatitis B and C proteins in comparison to recommended drugs Sofosbuvir and lamivudine. The results of molecular docking were based on binding affinity. Compound H_E, with a binding affinity of ‐7.6 kcal/mol has more potential in treating hepatitis than H_B, which has a binding affinity of ‐7.1 kcal/mol and is also a better anti‐hepatic agent than standard drugs sofosbuvir and lamivudine with lower binding affinities. Hence, H_E has the potential to treat HBV and HCV.

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“…Inspired by the above phenomenon, variable-temperature (VT) 1 H-NMR experiments were carried out to determine the percentage changes of the two configurational isomers, which revealed the configurational isomerism phenomenon. As density functional theory (DFT) calculations are widely used to determine NMR assignments for the characterization of complex structures [ 4 , 5 ], we performed DFT calculations to assign the NMR signals of these conformers. To our knowledge, this is the first report of the NMR assignment of configurational isomers of N-nitrosamines.…”

Section: Introductionmentioning

confidence: 99%

NMR Assignments of Six Asymmetrical N-Nitrosamine Isomers Determined in an Active Pharmaceutical Ingredient by DFT Calculations

et al. 2022

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N-nitrosamines, which are well-known pro-mutagens, are found in drugs, pickled food and tobacco. Therefore, controlling their concentrations is very important. When an HPLC, GC or NMR analysis is conducted to investigate certain asymmetrical N-nitrosamines, two sets of signals attributed to the asymmetric N-nitrosamine isomers are usually observed. However, few reports on the NMR assignment of asymmetrical N-nitrosamine isomers have been published. In this study, we investigated the NMR assignments of the Z/E isomers of six asymmetrical N-nitrosamines by means of density functional theory (DFT) calculations. The configuration of the major isomer of asymmetrical N-nitrosamine 3 was the Z-configuration. The configuration of the major isomers of asymmetrical N-nitrosamines 4–7 was the E-configuration. Then, we determined the Z/E ratios of these asymmetrical N-nitrosamines by means of variable temperature (VT) and room temperature (RT) 1H-NMR experiments. The ratios of the Z/E isomer 3 quickly increased beyond 100% in the VT 1H NMR experiments. The ratios of Z/E isomers 4–7 were increased in the range of 10–60% in the VT 1H NMR experiments. The results of this study indicate that identifying the isomers of asymmetrical N-nitrosamine is necessary to control the quality of N-nitrosamines for active pharmaceutical ingredients (APIs).

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Quantum Computational Investigation of (E)-1-(4-methoxyphenyl)-5-methyl-N′-(3-phenoxybenzylidene)-1H-1,2,3-triazole-4-carbohydrazide

Cited by 73 publications

References 72 publications

Post-Modification of Copolymers Obtained by ATRP for an Application in Heterogeneous Asymmetric Salen Catalysis

Post-Modification of Copolymers Obtained by ATRP for an Application in Heterogeneous Asymmetric Salen Catalysis

Synthesis, characterization, DFT studies, and molecular modeling of hydrazinelidene‐3‐oxo‐3‐(p‐olyl) propanal derivatives as potential candidate for Hepatitis B and C treatment

NMR Assignments of Six Asymmetrical N-Nitrosamine Isomers Determined in an Active Pharmaceutical Ingredient by DFT Calculations

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