دراسة نظرية آلياتيةلمشتقات البنزوكينولين
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Date
2024-02-28
Authors
Journal Title
Journal ISSN
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Publisher
UNIVERSITE MOHAMED BOUDIAF - M’SILA
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
o-phenylenediamine (2, X=NH) as strong nucleophiles 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
function (ELF) of the bending point structures along the reaction path indicates that the
reaction occurs via a non-concerted two-step mechanism. NCI analysis also showed
hydrogen bonds and non-covalent reactions in these compounds.
Description
Keywords
benzo/oxa/thia/dia/zepines fused quinoline, DFT Calculations, ELF Calculations, NCI Calculations, QTAIM Calculations, ASM/EDA model.