title: Understanding the high reactivity of triazolinediones in Diels-Alder reactions. A DFT study.
abstract: The participation of 4-substituted-1,2,4-triazoline-3,5-diones (TADs) in Diels-Alder reactions toward a series of dienes is studied at the M05-2X/6-31+G(d,p) level. These reactions show very low activation energies and complete endo selectivity, in agreement with the experimental data. For a dienic steroid model, the reaction presents an α-facial selectivity. Analysis of reactivity indices explains the superelectrophilic character of TADs, and low activation energy. The substituent and solvent effects are also evaluated.
authors.affiliation: Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, 72570, Puebla, Pue., Mexico, marieta.fernandez@correo.buap.mx.
authors.forename: María A
authors.initials: MA
authors.lastname: Fernández-Herrera
authors.forename: Claudia
authors.initials: C
authors.lastname: Zavala-Oseguera
authors.forename: José Luis
authors.initials: JL
authors.lastname: Cabellos
authors.forename: Jesús
authors.initials: J
authors.lastname: Sandoval-Ramírez
authors.forename: Luis R
authors.initials: LR
authors.lastname: Domingo
authors.forename: Gabriel
authors.initials: G
authors.lastname: Merino
mesh_terms: D008956:Models, Chemical; D008958:Models, Molecular; D012997:Solvents / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry*
chemical_list: D012997:Solvents; D014230:Triazoles