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Peer-reviewedCC BY-NCRSC advances

Computational study of regio- and stereoselectivity in aza-diene cycloadditions with ethyl vinyl ether and methyl acrylate as ethylene derivatives.

  • Mohamed Chellegui1,2
  • Lakhdar Benhamed3
  • Mohamed H Mohamed4
  • Ali Ben Ahmed5,6
6 affiliations
  1. 1Laboratory of Organic Chemistry (LR17ES08), Faculty of Sciences, University of Sfax Sfax 3038 Tunisia.
  2. 2Namur Institute of Structured Matter, University of Namur Rue de Bruxelles, 61 Namur B-5000 Belgium.
  3. 3Laboratory of Applied Thermodynamics and Molecular Modelling (LAT2M), Department of Chemistry, Faculty of Science, University of Tlemcen PB 119 Tlemcen 13000 Algeria.
  4. 4Mechanical Engineering Department, College of Engineering and Architecture, Umm Al-Qura University Makkah Saudi Arabia.
  5. 5Department of Biomedical, Higher Institute of Biotechnology of Sfax, University of Sfax BP 1175 3000 Sfax Tunisia [email protected].
  6. 6Laboratory of Applied Physics, Department of Physics, Faculty of Sciences, University of Sfax BP 1171 3000 Sfax Tunisia.
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Abstract

Within the context of Molecular Electronic Density Theory (MEDT), this study investigates the hetero-Diels-Alder (HDA) reaction among aza-diene 1 and ethyl vinyl ether 2a (reaction 1) and methyl acrylate 2b (reaction 2) applying Density Functional Theory (DFT) simulations at the M06-2X/6-311+G(d,p) level of approximation. The results of the local reactivity indices analysis based on the Parr functions confirmed the regiochemistry experimentally observed. Exploration of potential energy surfaces (PESs) indicated the formation of 2-ethoxy-4-phenyl-3,4-dihydro-2H-pyridine-6-carbonitrile α-regioisomer (reaction 1) and methyl 6-cyano-4-phenyl-3,4-dihydro-2H-pyridine-3-carboxylate β-regioisomer (reaction 2). Conceptual DFT reactivity indices show that 1-aza-butadiene is a strong electrophile, ethyl vinyl ether is a strong nucleophile, and methyl acrylate is a weak nucleophile. Electron localization function and quantum theory of atoms in molecules topological analyses of the electronic structures of the transition state structure reveal a high degree of similarity in their electron density distributions, highlighting the asynchronous nature of the reaction mechanism, a conclusion further supported by BET analysis, favoring a total agreement with experimental findings.

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Cite

BibTeXRIS
BibTeX
@article{chellegui2026computational,
  title = {{Computational study of regio- and stereoselectivity in aza-diene cycloadditions with ethyl vinyl ether and methyl acrylate as ethylene derivatives.}},
  author = {Mohamed Chellegui and Lakhdar Benhamed and Mohamed H Mohamed and Ali Ben Ahmed},
  journal = {RSC advances},
  year = {2026},
  month = oct,
  doi = {10.1039/d6ra07752h},
  url = {https://europepmc.org/article/MED/42835972},
  note = {CC BY-NC},
}
RIS
TY  - JOUR
TI  - Computational study of regio- and stereoselectivity in aza-diene cycloadditions with ethyl vinyl ether and methyl acrylate as ethylene derivatives.
AU  - Mohamed Chellegui
AU  - Lakhdar Benhamed
AU  - Mohamed H Mohamed
AU  - Ali Ben Ahmed
PY  - 2026
DA  - 2026/10/05
JO  - RSC advances
DO  - 10.1039/d6ra07752h
UR  - https://europepmc.org/article/MED/42835972
AB  - Within the context of Molecular Electronic Density Theory (MEDT), this study investigates the hetero-Diels-Alder (HDA) reaction among aza-diene 1 and ethyl vinyl ether 2a (reaction 1) and methyl acrylate 2b (reaction 2) applying Density Functional Theory (DFT) simulations at the M06-2X/6-311+G(d,p) level of approximation. The results of the local reactivity indices analysis based on the Parr functions confirmed the regiochemistry experimentally observed. Exploration of potential energy surfaces (PESs) indicated the formation of 2-ethoxy-4-phenyl-3,4-dihydro-2H-pyridine-6-carbonitrile α-regioisomer (reaction 1) and methyl 6-cyano-4-phenyl-3,4-dihydro-2H-pyridine-3-carboxylate β-regioisomer (reaction 2). Conceptual DFT reactivity indices show that 1-aza-butadiene is a strong electrophile, ethyl vinyl ether is a strong nucleophile, and methyl acrylate is a weak nucleophile. Electron localization function and quantum theory of atoms in molecules topological analyses of the electronic structures of the transition state structure reveal a high degree of similarity in their electron density distributions, highlighting the asynchronous nature of the reaction mechanism, a conclusion further supported by BET analysis, favoring a total agreement with experimental findings.
SN  - 2046-2069
ER  -