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Theoretical study of the regio- and stereoselectivity of the 1,3-DC reaction of 2,3,4,5-tetrahydropyridine-l-oxide with methyl crotonate


 
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1. Title Title of document Theoretical study of the regio- and stereoselectivity of the 1,3-DC reaction of 2,3,4,5-tetrahydropyridine-l-oxide with methyl crotonate
 
2. Creator Author's name, affiliation, country H. Hazhazi; Laboratoire de Chimie Moléculaire et Environnement (LCME), Equipe de Chimie Informatique et Pharmaceutique (ECIP), Faculté des Sciences et Sciences Exacte - Département des sciences de la matière, Université de Biskra, BP 145 RP, 07000 Biskra, Algérie; Algeria
 
2. Creator Author's name, affiliation, country Y. Boumedjane; Laboratoire de Chimie Moléculaire et Environnement (LCME), Equipe de Chimie Informatique et Pharmaceutique (ECIP), Faculté des Sciences et Sciences Exacte - Département des sciences de la matière, Université de Biskra, BP 145 RP, 07000 Biskra, Algérie; Algeria
 
2. Creator Author's name, affiliation, country B. M essaoudi; Laboratoire de Thermodynamique Appliquée et Modélisation Moléculaire, Département de Chimie, Faculté des Sciences, Université A. Belkaid, BP 119, Tlemcen, 13000, Algérie; Algeria
 
3. Subject Discipline(s)
 
3. Subject Keyword(s) 1,3-Dipolar cycloaddition; 2,3,4,5-tetrahydropyridine-l-oxide; Selectivity; DFT calculations
 
4. Description Abstract

A theoretical study of the regio- and stereoselectivities of the 1,3-dipolar cycloaddition reaction between methyl crotonate and 2,3,4,5-tetrahydropyridine-l-oxide has been carried out using density functional theory (DFT) calculations at B3LYP/6-31G(d) level of theory. Analysis of the global reactivity and local electrophilicity indices has been used to explaining the regioselectivity of the titled reaction. Overall, our results show that the studied 1, 3-dipolar cycloaddition reactions favor the formation of the meta-endo cycloadduct in both cases. The bond order and charge transfer at the transition states and activation energies indicate that these reactions proceed via an asynchronous concerted mechanism. Thermodynamic and kinetic quantities for the possible stereoisomeric and regioisomeric pathways have been calculated at gas and solvent phase. Solvent effects do not modify the gas-phase selectivities but slightly increases the reactivity of the reagents. A good concordance is found between the obtained results and the experimental outcomes.
 
5. Publisher Organizing agency, location
 
6. Contributor Sponsor(s)
 
7. Date (YYYY-MM-DD) 09-10-2016
 
8. Type Status & genre Peer-reviewed Article
 
8. Type Type
 
9. Format File format PDF
 
10. Identifier Uniform Resource Identifier https://revues.imist.ma/index.php/morjchem/article/view/6383
 
10. Identifier Digital Object Identifier (DOI) https://doi.org/10.48317/IMIST.PRSM/morjchem-v4i4.6383
 
11. Source Title; vol., no. (year) Moroccan Journal of Chemistry; Vol 4, No 4 (2016)
 
12. Language English=en en
 
13. Relation Supp. Files
 
14. Coverage Geo-spatial location, chronological period, research sample (gender, age, etc.)
 
15. Rights Copyright and permissions Copyright (c)