DFT study of the condensation products of 2-chloro-3-formylquinolines with o-aminophenol, o-aminothiophenol and o-phenylenediamine - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Theoretical Chemistry Accounts: Theory, Computation, and Modeling Année : 2023

DFT study of the condensation products of 2-chloro-3-formylquinolines with o-aminophenol, o-aminothiophenol and o-phenylenediamine

Résumé

The reaction mechanism for the synthesis of quinoline fused benzo/dia/oxa/thia/zepins is investigated using the DFT/B3LYP/6-31G(d) method. DFT conceptual reactivity indices analysis allows classification of o-aminophenol (2, X=O), o-aminothiophenol (2, X=S) and ophenylenediamine (2, X=N) and R-substituted 2-chloroquinoline-3-carbaldehydes (1 ac) as strong electrophiles, suggesting a polar process. Besides Parr functions and Fukui indices predict the most reactive sites for observed experimentally product formation, in agreement with the dual descriptor analysis. In the energy aspect, there is no effect of the R (R=CH3, OCH3) substituent on the thermodynamic quantities whereas the substitution of the X has a remarkable effect. The products (4a-c, X = N) are the most stable and their cyclizations are the easiest. An extended analysis was performed using the activation strain model/energy decomposition analysis ASM/EDA model. The obtained results indicate that the orbital interaction and electrostatic stabilizations are the principal factors favoring the reaction with X=N. Topological analysis of the electron localization 2 function (ELF) of the bending point structures along the reaction path indicates that the reaction occurs via a non-concerted two-step mechanism.
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hal-04279862 , version 1 (10-11-2023)

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Nabila Benabila, Hafida Merouani, Nadjia Latelli, Abd Alghani May, Christophe Morell, et al.. DFT study of the condensation products of 2-chloro-3-formylquinolines with o-aminophenol, o-aminothiophenol and o-phenylenediamine. Theoretical Chemistry Accounts: Theory, Computation, and Modeling, 2023, 142 (11), pp.111. ⟨10.1007/s00214-023-03052-2⟩. ⟨hal-04279862⟩
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