title: A Theoretical Study of the Relationship between the Electrophilicity ω Index and Hammett Constant σpin [3+2] Cycloaddition Reactions of Aryl Azide/Alkyne Derivatives.
abstract: The relationship between the electrophilicity ω index and the Hammett constant σphas been studied for the [2+3] cycloaddition reactions of a series ofpara-substituted phenyl azides towardspara-substituted phenyl alkynes. The electrophilicity ω index-a reactivity density functional theory (DFT) descriptor evaluated at the ground state of the molecules-shows a good linear relationship with the Hammett substituent constants σp. The theoretical scale of reactivity correctly explains the electrophilic activation/deactivation effects promoted by electron-withdrawing and electron-releasing substituents in both azide and alkyne components.
authors: Laboratoire de Chimie Analytique et Moléculaire, Faculté Polydisciplinaire de Safi, Université Cadi Ayyad, Safi 46010, Morocco. belayou@gmail.com.
authors: Hicham
authors: H
authors: Ben El Ayouchia
authors: Laboratoire de Chimie Analytique et Moléculaire, Faculté Polydisciplinaire de Safi, Université Cadi Ayyad, Safi 46010, Morocco. ananehafid@gmail.com.
authors: Hafid
authors: H
authors: Anane
authors: Laboratoire de Chimie Analytique et Moléculaire, Faculté Polydisciplinaire de Safi, Université Cadi Ayyad, Safi 46010, Morocco. ml_elidrissi@yahoo.fr.
authors: Moulay Lahcen
authors: ML
authors: El Idrissi Moubtassim
authors: Departamento de Química Orgánica, Universidad de Valencia, Avda. Dr. Moliner 50, Burjassot 46100, Valencia, Spain. domingo@utopia.uv.es.
authors: Luis R
authors: LR
authors: Domingo
authors: Instituto de Ciencia Molecular/ICMol, Universidad de Valencia, C/Catedrático José Beltrán No. 2, Paterna 46980, Valencia, Spain. miguel.julve@uv.es.
authors: Miguel
authors: M
authors: Julve
authors: Laboratoire de Chimie Analytique et Moléculaire, Faculté Polydisciplinaire de Safi, Université Cadi Ayyad, Safi 46010, Morocco. stiriba@uv.es.|Instituto de Ciencia Molecular/ICMol, Universidad de Valencia, C/Catedrático José Beltrán No. 2, Paterna 46980, Valencia, Spain. stiriba@uv.es.
authors: Salah-Eddine
authors: SE
authors: Stiriba
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D008956:Models, Chemical
chemical_list: D000480:Alkynes; D001386:Azides
keywords: Hammett constants; [2+3] cycloaddition reactions; arylalkynes; arylazides; electrophilicity index; substituent effects