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Elucidation of the chemo- and stereoselectivity of [1+2] cycloaddition reactions between -cis-himachalene and dichlorocarbene using a multiphilic descriptor


 
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1. Title Title of document Elucidation of the chemo- and stereoselectivity of [1+2] cycloaddition reactions between -cis-himachalene and dichlorocarbene using a multiphilic descriptor
 
2. Creator Author's name, affiliation, country H. Hammal; R. Hammal1, Ahmed Benharref2 and Abdeslam El Hajbi1*
 
2. Creator Author's name, affiliation, country A. Benharref
 
2. Creator Author's name, affiliation, country A. Elhajbi; Laboratoire de Chimie Appliquée et Environnement (LCAE) (URAC-18). Centre Régional des Métiers de l'Education et de la Formation ''CRMEF''. de la Région orientale.; Morocco
 
3. Subject Discipline(s)
 
3. Subject Keyword(s) Keywords: [1+2] cycloaddition; Stereoselectivity; DFT-based reactivity index; a-cis-himachalene.
 
4. Description Abstract

A theoretical study of the mechanism and selectivity of [1+2] cycloaddition reactions between a-cis-himachalene and dichlorocarbene was performed using DFT B3LYP/6-311+G(d, p). Analysis of the global electrophilicity indeces shows that a-cis-himachalene behaves as a nucleophile, while dichlorocarbene behaves as an electrophile. In line with the local philicity concept, we propose a multiphilic descriptor. This descriptor is capable of simultaneously explaining the nucleophilicity and electrophilicity of the atomic sites in the molecule. The double bond of the six-membered ring is attacked when stoichiometric quantities of a-cis-himachalene and dichlorocarbene are used, while the other double bond is attacked by dichlorocarbene only when it is used in excess. The calculation of activation and reaction energies indicates that the a cycloadducts are favored both kinetically and thermodynamically

 
 
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/4722
 
10. Identifier Digital Object Identifier (DOI) https://doi.org/10.48317/IMIST.PRSM/morjchem-v4i4.4722
 
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)