Nucleophilicity of 4‐(Alkylthio)‐3‐imidazoline Derived Enamines

Hensinger, Magenta J.; Eitzinger, Andreas; Trapp, Oliver; Ofial, Armin R.

doi:10.1002/chem.202302764

Cited by 2 publications

References 76 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.

View full text Add to dashboard Cite

show abstract

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

Preprint

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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 (Epox) 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 (R2 = 0.9957) between the experimental nucleophilicity (N) and the theoretical model of nucleophilicity (ω−1) determined in this work of various 5-R-substituted indoles has been obtained and discussed.

show abstract

Nucleophilicity of 4‐(Alkylthio)‐3‐imidazoline Derived Enamines

Cited by 2 publications

References 76 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

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

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