Understanding the Mechanism of Diels–Alder Reactions with Anionic Dienophiles: A Systematic Comparison of [ECX]<sup>−</sup> (E = P, As; X = O, S, Se) Anions
A. HORVATH, Zoltán Benkő
Abstract
anions. Furthermore, analysis of the geometries and electron distributions of the corresponding transition states revealed structure-property relationships, and thus a direct comparison of the cycloaddition reactivity of these anions was achieved. Along one of the two pathways, a good correlation was found between the activation barriers and suitable nucleophilicity descriptors (nucleophilic Parr function and global nucleophilicity). Additionally, the tendency of the reaction energies can be explained by the changing aromaticity of the products.
Topics & Concepts
ChemistryNucleophileReactivity (psychology)Cationic polymerizationCycloadditionRegioselectivityTransition stateComputational chemistryConcerted reactionReaction mechanismMedicinal chemistryStereochemistryOrganic chemistryCatalysisAlternative medicinePathologyMedicineOrganic Chemistry Cycloaddition ReactionsChemical Reaction MechanismsChemistry and Chemical Engineering