Reactivity Indices related to DFT Theory, the Electron Localization Function (ELF) and Non-Covalent Interactions (NCI) Calculations in the Formation of the non-Halogenated Pyruvic Esters in Solution

Jorio, S.; Salah, Mohammed; Makarim, Hassna Abou El; Tabyaoui, Mohamed

doi:10.13171/mjc8619072612sj

Cited by 23 publications

(11 citation statements)

References 44 publications

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“…The global reactivity parameters, ionization potential (IP), electron affinity (EA), global softness (σ), global electrophilicity (ω), global hardness (η), global electronegativity ( X ), and chemical potential (μ), were computed using the FMOs energies (Table ) according to eqs – (see Section ), − and the computed values in eV are presented in Table .…”

Section: Computational Resultsmentioning

confidence: 99%

Preparation, Crystal Structure, Supramolecular Assembly, and DFT Studies of Two Organic Salts Bearing Pyridine and Pyrimidine

et al. 2023

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The effective preparation of two new pyrimidine- and pyridine-based organic crystalline salts with substituted acidic moieties (i.e., (Z)-4-(naphthalen-2-ylamino)-4-oxobut-2-enoic acid (DCNO) and 2-hydroxy-3,5-dinitrobenzoic acid (PCNP)) using methanol as a solvent has been reported. These molecular salts have ionic interactions that are responsible for their structural stabilization in their solid-state assemblies. The crystal structures of DCNO and PCNP were determined by the single-crystal X-ray diffraction (SCXRD) technique. The SCXRD study inferred that cations and anions are strongly packed due to N–H···O, N–H···N, and C–H···O noncovalent interactions in DCNO, whereas in PCNP, N–H···N noncovalent interactions are absent. The noncovalent interactions in both organic crystalline salts were comprehensively investigated by Hirshfeld surface analysis. Further, a detailed density functional theory (DFT) study of both compounds was performed. The optimized structures of both compounds supported the existence of the H-bonding and weak dispersion interactions in the synthesized organic crystalline salt structures. Both compounds were shown to have large and noticeably different HOMO/LUMO energy gaps. The atomic charge analysis results supported the SCXRD and HSA results, showing the formation of intermolecular noncovalent interactions in both organic crystalline salts. The results of the natural bond orbital (NBO) analysis confirmed the existence of (relatively weak) noncovalent interactions between the cation and anion moieties of their organic crystalline salts. The global reactivity parameters (GRPs) analysis showed that both organic crystalline salts’ compounds should be quite thermodynamically stable and that DCNO should be less reactive than PCNP. For both compounds, the molecular electrostatic potential (MEP) analysis results support the existence of intermolecular electrostatic interactions in their organic crystalline salts.

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Section: Computational Resultsmentioning

confidence: 99%

Preparation, Crystal Structure, Supramolecular Assembly, and DFT Studies of Two Organic Salts Bearing Pyridine and Pyrimidine

et al. 2023

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“…We consider the calculated structures of the seven isomers of 4-hydroxyisoleucine, structural parameters for the lowest-lying isomer, its NBO charges, FMOs, and MEP. Furthermore, we used the values of the energies of the lowest-lying isomer, HOMO and LUMO, to compute its global reactivity parameters (GRP) ( Geerlings et al, 2003 ; Chakraborty et al, 2013 ; Jorio et al, 2019 ) (Eqs 1 – 6 ). Eqs 1 , 2 were used to calculate the values of the ionization potential ( IP ) and electron affinity ( EA ):

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Section: Methodsmentioning

confidence: 99%

Computational pharmacology and computational chemistry of 4-hydroxyisoleucine: Physicochemical, pharmacokinetic, and DFT-based approaches

et al. 2023

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Computational pharmacology and chemistry of drug-like properties along with pharmacokinetic studies have made it more amenable to decide or predict a potential drug candidate. 4-Hydroxyisoleucine is a pharmacologically active natural product with prominent antidiabetic properties. In this study, ADMETLab 2.0 was used to determine its important drug-related properties. 4-Hydroxyisoleucine is compliant with important drug-like physicochemical properties and pharma giants’ drug-ability rules like Lipinski’s, Pfizer, and GlaxoSmithKline (GSK) rules. Pharmacokinetically, it has been predicted to have satisfactory cell permeability. Blood–brain barrier permeation may add central nervous system (CNS) effects, while a very slight probability of being CYP2C9 substrate exists. None of the well-known toxicities were predicted in silico, being congruent with wet lab results, except for a “very slight risk” for respiratory toxicity predicted. The molecule is non ecotoxic as analyzed with common indicators such as bioconcentration and LC50 for fathead minnow and daphnia magna. The toxicity parameters identified 4-hydroxyisoleucine as non-toxic to androgen receptors, PPAR-γ, mitochondrial membrane receptor, heat shock element, and p53. However, out of seven parameters, not even a single toxicophore was found. The density functional theory (DFT) study provided support to the findings obtained from drug-like property predictions. Hence, it is a very logical approach to proceed further with a detailed pharmacokinetics and drug development process for 4-hydroxyisoleucine.

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“…Below, we consider the structures and energetics, natural population analysis (NPA) charges [ 32 ], frontier molecular orbitals (FMOs), and molecular electrostatic potential (MEP) maps for all compounds obtained with the implicit effects from water. Additionally, we used the values of the energies of highest occupied molecular orbital (HOMO)–lowest unoccupied molecular orbital (LUMO) to compute the global reactivity parameters (GRPs) [ 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 ] (Equations (1)–(6)).…”

Section: Methodsmentioning

confidence: 99%

“…All 18 synthesized compounds were then characterized using standard analytical techniques such as FTIR (Fourier transform infrared spectroscopy), NMR (nuclear magnetic resonance spectroscopy), mass, and elemental analyses and subjected to in vitro anti-bacterial analysis on selected strains (please refer to Figures S1–S60 for spectral data). Furthermore, the DFT (density functional theory) method is used to calculate the global chemical reactivity descriptors of the title molecules, such as chemical hardness, energy, electronic chemical potential, and electrophilicity [ 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 ]. These descriptors are employed to predict the relative stability and reactivity of the molecules.…”

Section: Introductionmentioning

confidence: 99%

Theoretical and Anti-Klebsiella pneumoniae Evaluations of Substituted 2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide and Imidazopyridine Hydrazide Derivatives

et al. 2023

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A series of multistep synthesis protocols was adopted to synthesize substituted imidazopyridines (IMPs) (SM-IMP-01 to SM-IMP-13, and DA-01-05). All substituted IMPs were then characterized using standard spectroscopic techniques such as 1H-NMR, 13C-NMR, elemental analyses, and mass spectrometry. Our both in vitro qualitative and quantitative results for antibacterial analysis, against Klebsiella pneumoniae ATCC 4352 and Bacillus subtilis ATCC 6051 suggested that all compounds essentially exhibited activity against selected strains of bacteria. Our DFT analyses suggested that the compounds of the SM-IMP-01–SM-IMP-13 series have HOMO/LUMO gaps within 4.43–4.69 eV, whereas the compounds of the DA-01–DA-05 series have smaller values of the HOMO/LUMO gaps, 3.24–4.17 eV. The lowest value of the global hardness and the highest value of the global softness, 2.215 and 0.226 eV, respectively, characterize the compound SM-IMP-02; thus, it is the most reactive compound in the imidazopyridine carboxamide series (except hydrazide series). This compound also depicted lesser MIC values against Klebsiella pneumoniae ATCC 4352 and Bacillus subtilis ATCC 6051 as 4.8 µg/mL, each. In terms of another series, hydrazide DA-05 depicted strong antimicrobial actions (MIC: 4.8 µg/mL against both bacterial strains) and also had the lowest energy gap (3.24 eV), higher softness (0.309 eV), and lesser hardness (1.62 eV). Overall, when we compare qualitative and quantitative antimicrobial results, it is been very clear that compounds with dibromo substitutions on imidazopyridine (IMP) rings would act as better antimicrobial agents than those with -H at the eighth position on the IMP ring. Furthermore, substituents of higher electronegativities would tend to enhance the biological activities of dibromo-IMP compounds. DFT properties were also well comparable to this trend and overall, we can say that the electronic behavior of compounds under investigation has key roles in their bioactivities.

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Reactivity Indices related to DFT Theory, the Electron Localization Function (ELF) and Non-Covalent Interactions (NCI) Calculations in the Formation of the non-Halogenated Pyruvic Esters in Solution

Cited by 23 publications

References 44 publications

Preparation, Crystal Structure, Supramolecular Assembly, and DFT Studies of Two Organic Salts Bearing Pyridine and Pyrimidine

Preparation, Crystal Structure, Supramolecular Assembly, and DFT Studies of Two Organic Salts Bearing Pyridine and Pyrimidine

Computational pharmacology and computational chemistry of 4-hydroxyisoleucine: Physicochemical, pharmacokinetic, and DFT-based approaches

Theoretical and Anti-Klebsiella pneumoniae Evaluations of Substituted 2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide and Imidazopyridine Hydrazide Derivatives

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