Exploring the reactivity of benzotriazole derivatives: Mayr's approach and density functional theory analysis

Rammah, Mehdi; Mahdhaoui, Faouzi; Ayachi, S.; Boubaker, Taoufik

doi:10.1016/j.molstruc.2021.131310

Journal of Molecular Structure

2022

DOI: 10.1016/j.molstruc.2021.131310

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Exploring the reactivity of benzotriazole derivatives: Mayr's approach and density functional theory analysis

Mehdi Rammah

Faouzi Mahdhaoui

S. Ayachi

et al.

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Cited by 7 publications

References 40 publications

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Combined kinetic, and theoretical approaches for the study of the SEAr reactions of 2-(2′,4′,6′-trinitrophenyl)-4,6-dinitrobenzotriazole 1-oxide with 5-R-substituted indoles in acetonitrile

Amamou,

Hedhli,

Slama

et al. 2024

Chem. Pap.

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We present a kinetic and theoretical study of nucleophilic addition reactions involving 2-(2',4',6'-trinitrophenyl)-4,6-dinitrobenzotriazole 1-oxide 1 with a series of 5-R-substituted indoles 2a-e (R = CN, Cl, H, Me and NH2) in acetonitrile at 20 °C. Single electron transfer (SET) mechanism was proposed and confirmed by the agreement between the rate constants (k) and the oxidation potentials (Ep ox ) of these series of indoles. Using Mayr's equation, the electrophilicity parameter (E) of 1 at C-7 position is derived and compared with the same parameter estimate using empirical equation E vs. pKa. Density Functional Theory (DFT) calculations were performed to confirm the suggested reaction mechanisms and elucidate the origin of the electrophilic reactivity of 1. Notably, a linear correlation (R 2 = 0.9957) between the experimental nucleophilicity (N) and the theoretical model of nucleophilicity ( -1 ) determined in this work of various 5-R-substituted indoles has been obtained and discussed.

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Combined kinetic, and theoretical approaches for the study of the SEAr reactions of 2-(2′,4′,6′-trinitrophenyl)-4,6-dinitrobenzotriazole 1-oxide with 5-R-substituted indoles in acetonitrile

Amamou,

Hedhli,

Slama

et al. 2024

Chem. Pap.

Self Cite

View full text Add to dashboard Cite

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A theoretical and electrochemical impedance spectroscopy study of the adsorption and sensing of selected metal ions by 4-morpholino-7-nitrobenzofuran

Chérif,

Gassoumi,

Ayachi

et al. 2024

Heliyon

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Electrophilicity, mechanism and structure–reactivity relationships of cyclic secondary amines addition to 2-methoxy-3,5-dinitropyridine

Slama,

Amamou,

Hedhli

et al. 2024

Journal of Molecular Structure

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Exploring the reactivity of benzotriazole derivatives: Mayr's approach and density functional theory analysis

Cited by 7 publications

References 40 publications

Combined kinetic, and theoretical approaches for the study of the SEAr reactions of 2-(2′,4′,6′-trinitrophenyl)-4,6-dinitrobenzotriazole 1-oxide with 5-R-substituted indoles in acetonitrile

Combined kinetic, and theoretical approaches for the study of the SEAr reactions of 2-(2′,4′,6′-trinitrophenyl)-4,6-dinitrobenzotriazole 1-oxide with 5-R-substituted indoles in acetonitrile

A theoretical and electrochemical impedance spectroscopy study of the adsorption and sensing of selected metal ions by 4-morpholino-7-nitrobenzofuran

Electrophilicity, mechanism and structure–reactivity relationships of cyclic secondary amines addition to 2-methoxy-3,5-dinitropyridine

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