Correlation of the Homo–Lumo Gap in Furyl and Thienyl Nitrones and Nitroethenes with their Electrochemical Redox Potentials*

Boulkroune, M.; Игнатович, Л.; Muravenko, V.; Spura, Jana; Chibani, Aïssa; Jouikov, Viatcheslav

doi:10.1007/s10593-014-1409-3

Cited by 5 publications

(2 citation statements)

References 17 publications

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“…. Quite similar trends were previously found for furyl and thienyl nitrones and nitroethenes [36]. When considered in terms of orbital hardness, furyl-and thienylsubstituted aldimines form two different groups (Fig.…”

Section: Dft Modelingsupporting

confidence: 84%

Novel R3M (M = Si, Ge) substituted furan and thiophene-derived aldimines: Synthesis, electrochemistry, and biological activity

Spura

Farhati

Romanovs

et al. 2019

Comptes Rendus. Chimie

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New furan and thiophene derivatives of aldimines o-HO-C 6 H 4 N]CHC 4 H 4 X(R) (X ¼ O, S; R ¼ H, SiMe 3 , SiEt 3 , GeMe 3 , GeEt 3 ) were synthesized by condensation of o-aminophenol with the substituted aldehyde precursor. Their structure, electrochemical reduction/oxidation (in CH 3 CN/0.1 M Bu 4 NPF 6 ), frontier orbital energies, and cytotoxicity have been studied. Their electrochemical redox potentials E p show good correlation with the corresponding orbital energies and the difference E p ox e E p red corresponds well to their orbital hardness.These new compounds have a pronounced cytotoxicity toward cancer cells of human fibrosarcoma HT-1080 and mouse hepatoma MG-22A (IC 50 y 1e8 mg ml À1 ) that can be modulated by introducing a Me 3 M substituent into the fifth position of the heterocycle (e.g., IC 50 (Me 3 Si)/IC 50 (H) ! 50). R 3 M-substitution reduces the orbital hardness of the aldimines studied and facilitates oxidation, promoting their oxidative metabolism. The neighboring group effect in the a-Me 3 Si-substituted thiophene derivative favors S-oxidation, which supposedly makes its metabolic mechanism different compared to R 3 Msubstituted furan series (or for M ¼ Ge in the thiophene series). Interestingly, SiMe 3 and GeMe 3 groups in both heterocyclic series (furan and thiophene) cause opposite trends in cytotoxicity, while the silyl group increases it, the germyl group decreases it.

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Section: Dft Modelingsupporting

confidence: 84%

Novel R3M (M = Si, Ge) substituted furan and thiophene-derived aldimines: Synthesis, electrochemistry, and biological activity

Spura

Farhati

Romanovs

et al. 2019

Comptes Rendus. Chimie

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“…Thus, the computer-aided investigation has proven a pertinent approach to identify key parameters for designing novel ligands with better electrochemical properties. Generally, previous computations are based on the correlation of electrochemical oxidation and reduction potentials, with energy levels corresponding to the lowest unoccupied molecular orbital (LUMO) or the highest occupied molecular orbital (HOMO), respectively [27][28][29]. For such quantum computations, the use of the B3LYP level of theory has led to strong linear correlations between the energy of the HOMO/LUMO orbitals and redox potentials [30].…”

Section: Introductionmentioning

confidence: 99%

Properties Assessment by Quantum Mechanical Calculations for Azulenes Substituted with Thiophen– or Furan–Vinyl–Pyridine

et al. 2022

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In this paper, azulenes substituted with thiophen– or furan–vinyl–pyridine are reported as heavy metal ligands in systems based on chemically modified electrodes. We undertook a computational study of their structures using density functional theory (DFT). Based on these computations, we obtained properties and key molecular descriptors related to chemical reactivity and electrochemical behavior. We investigated the correlation between some quantum parameters associated with the chemical reactivity and the complexing properties of the modified electrodes based on these ligands. The best correlations for the parameters were retained. We showed that the linear correlation between DFT-computed HOMO/LUMO energies and experimental redox potentials is very good.

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Antidiabetic and antioxidant activities: Is there any link between them?

et al. 2019

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show abstract

Correlation of the Homo–Lumo Gap in Furyl and Thienyl Nitrones and Nitroethenes with their Electrochemical Redox Potentials*

Cited by 5 publications

References 17 publications

Novel R3M (M = Si, Ge) substituted furan and thiophene-derived aldimines: Synthesis, electrochemistry, and biological activity

Novel R3M (M = Si, Ge) substituted furan and thiophene-derived aldimines: Synthesis, electrochemistry, and biological activity

Properties Assessment by Quantum Mechanical Calculations for Azulenes Substituted with Thiophen– or Furan–Vinyl–Pyridine

Antidiabetic and antioxidant activities: Is there any link between them?

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