Spectral investigation, TD-DFT study, Hirshfeld surface analysis, NCI-RDG, HOMO-LUMO, chemical reactivity and NLO properties of 1-(4-fluorobenzyl)-5-bromolindolin-2,3‑dione

Boukabcha, Nourdine; Benmohammed, Abdelmadjid; Belhachemi, Mohammed Hadj Mortada; Goudjil, Meriem; Yahiaoui, Salem; Megrouss, Youcef; Djafri, Ahmed; Khelloul, Nawel; Benyehlou, Zohra Douaa; Djafri, Ayada; Chouaih, Abdelkader

doi:10.1016/j.molstruc.2023.135492

Cited by 37 publications

(6 citation statements)

References 63 publications

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“…Analyzing the E gap values collected in Table 2, it was found that, regardless of the solvent model used, the most reactive monoterpene is thymol, which is characterized by the lowest stability, while menthol will be the least reactive of the group of compounds tested. It was also observed that, depending on the tested monoterpene, E gap (E gap = E LUMO − E HOMO [83,84]) can be used to determine the dependency on the solvent model used. For example, on the basis of the data collected in Figure 1, which visualize the surfaces of the HOMO, the LUMO molecular orbitals with their corresponding energies for different ε for limonene, it can be observed that the HOMO-LUMO energy difference increases with increasing ε and is the largest for water, then acetonitrile, and then methanol.…”

Section: Resultsmentioning

confidence: 99%

“…GCRDs are defined for monoterpene molecules in their singlet ground state with the DFT of Parr, Pearson, and Yang [85]. The ionization potential (I), correlated with -E HOMO , is the minimum energy that is necessary to remove an electron from a monoterpene molecule [84]. In all the cases listed in Table 3, thymol has the lowest ionization potential value, followed by pinene, limonene, and cymene.…”

Section: Gasmentioning

confidence: 99%

“…In turn, menthol has the lowest A value in all the tested solvent models. The electronegativity (X) values, i.e., the measure of the tendency to "attract" electrons [84], is defined as X = 0.5•(I + A) [86][87][88] and increase in series: pinene, limonene, thymol, cymene, and menthol with the highest value. Global hardness (η) according to Parr and Pearson-first-order derivative of the chemical potential with respect to the total number of electrons N, with a constant external potential, or secondorder derivative of energy (also with respect to the number of electrons N, at a constant external potential).…”

Section: Gasmentioning

confidence: 99%

“…The last column of Table 3 applies to µ, which describes the chemical potential; µ = −0.5•(I + A) [90]. Chemical potential shows the sensitivity of the system to changes in electrons, a high µ indicates that the molecule has the properties of a strong electron acceptor, while a low µ characterizes strong electron donors [84]. Of the compounds analyzed, menthol has the lowest µ value; a low µ and high ω for a molecule indicate its good electrophilic nature.…”

Section: Gasmentioning

confidence: 99%

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DFT Studies of the Activity and Reactivity of Limonene in Comparison with Selected Monoterpenes

Rydel-Ciszek

2024

Molecules

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Nowadays, the effective processing of natural monoterpenes that constitute renewable biomass found in post-production waste into products that are starting materials for the synthesis of valuable compounds is a way to ensure independence from non-renewable fossil fuels and can contribute to reducing global carbon dioxide emissions. The presented research aims to determine, based on DFT calculations, the activity and reactivity of limonene, an organic substrate used in previous preparative analyses, in comparison to selected monoterpenes such as cymene, pinene, thymol, and menthol. The influence of the solvent model was also checked, and the bonds most susceptible to reaction were determined in the examined compounds. With regard to EHOMO, it was found that limonene reacts more easily than cymene or menthol but with more difficultly than thymol and pienene. The analysis of the global chemical reactivity descriptors “locates” the reactivity of limonene in the middle of the studied monoterpenes. It was observed that, among the tested compounds, the most reactive compound is thymol, while the least reactive is menthol. The demonstrated results can be a reference point for experimental work carried out using the discussed compounds, to focus research on those with the highest reactivity.

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Section: Resultsmentioning

confidence: 99%

Section: Gasmentioning

confidence: 99%

Section: Gasmentioning

confidence: 99%

Section: Gasmentioning

confidence: 99%

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DFT Studies of the Activity and Reactivity of Limonene in Comparison with Selected Monoterpenes

Rydel-Ciszek

2024

Molecules

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“…This hybrid function represents a Generalized Gradient Approximation (GGA) and, as demonstrated in prior research, provides better agreement with experimental results. Furthermore, B3LYP is widely utilized in molecular simulations of transition metal catalytic systems [ 18 , 19 , 20 ], offering more accurate and reliable results than other methods. After geometry optimizations, energy values were obtained using the same function with the 6-311G basis set.…”

Section: Methodsmentioning

confidence: 99%

Study of the Chemical Activities of Carbon Monoxide, Carbon Dioxide, and Oxygen Traces as Critical Inhibitors of Polypropylene Synthesis

Hernández-Fernández,

Puello-Polo,

Marquez

2024

Polymers

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This study outlines the investigation into how the compounds CO2, CO, and O2 interact with the active center of titanium (Ti) on the surface of MgCl2 and how these interactions impact the productivity of the Ziegler–Natta catalyst, ultimately influencing the thermal stability of the produced polypropylene. The calculations revealed that the adsorption energies of Ti-CO2-CO and O2 were −9.6, −12.5, and −2.32 Kcal/mol, respectively. Using the density functional theory in quantum calculations, the impacts of electronic properties and molecular structure on the adsorption of CO, O2, and CO2 on the Ziegler–Natta catalyst were thoroughly explored. Additionally, the Gibbs free energy and enthalpy of adsorption were examined. It was discovered that strong adsorption and a significant energy release (−16.2 kcal/mol) during CO adsorption could explain why this gas caused the most substantial reductions in the ZN catalyst productivity. These findings are supported by experimental tests showing that carbon monoxide has the most significant impact on the ZN catalyst productivity, followed by carbon dioxide, while oxygen exerts a less pronounced inhibitory effect.

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Red‐emitting 4‐methyl coumarin fused barbituric acid as an electrochemical sensor for catechol detection and probe for latent fingerprints

Yashyanaik,

Venkatesh,

Ereshnaik

et al. 2024

Luminescence

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Herein, we have reported a red‐emitting 4‐methyl coumarin fused barbituric acid azo dye (4‐MCBA) synthesized by conventional method. Density functional theory (DFT) studies of tautomer compounds were done using (B3LYP) with a basis set of 6‐31G(d,p). NLO analysis has shown that tautomer has mean first‐order hyperpolarisabilities (β) value of 1.8188 × 10−30 esu and 1.0470 × 10−30 esu for azo and hydrazone forms, respectively, which is approximately nine and five times greater than the magnitude of urea. 4‐MCBA exhibited two absorption peaks in the range of 290–317 and 379–394 nm, and emission spectra were observed at 536 nm. CV study demonstrated that the modified 4‐MCBA/MGC electrode exhibited excellent electrochemical sensitivity towards the detection of catechol and the detection limit is 9.39 μM under optimum conditions. The 4‐MCBA employed as a fluorescent probe for the visualisation of LFPs on various surfaces exhibited Level‐I to level‐II LFPs, with low background interference.

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Spectral investigation, TD-DFT study, Hirshfeld surface analysis, NCI-RDG, HOMO-LUMO, chemical reactivity and NLO properties of 1-(4-fluorobenzyl)-5-bromolindolin-2,3‑dione

Cited by 37 publications

References 63 publications

DFT Studies of the Activity and Reactivity of Limonene in Comparison with Selected Monoterpenes

DFT Studies of the Activity and Reactivity of Limonene in Comparison with Selected Monoterpenes

Study of the Chemical Activities of Carbon Monoxide, Carbon Dioxide, and Oxygen Traces as Critical Inhibitors of Polypropylene Synthesis

Red‐emitting 4‐methyl coumarin fused barbituric acid as an electrochemical sensor for catechol detection and probe for latent fingerprints

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