DFT study of the condensation products of 2-chloro-3-formylquinolines with o-aminophenol, o-aminothiophenol and o-phenylenediamine - Archive ouverte HAL Access content directly
Journal Articles Theoretical Chemistry Accounts: Theory, Computation, and Modeling Year : 2023

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

Abstract

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.
Fichier principal
Vignette du fichier
hafida_v9c_BW.pdf (752.19 Ko) Télécharger le fichier
Origin : Files produced by the author(s)

Dates and versions

hal-04279862 , version 1 (10-11-2023)

Identifiers

Cite

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⟩
14 View
16 Download

Altmetric

Share

Gmail Facebook X LinkedIn More