Understanding the Reactivity of C-Cyclopropyl-N-Methylnitrone Participating in [3+2] Cycloaddition Reactions Towards Styrene with a Molecular Electron Density Theory Perspective

Abstract. The [3+2] cycloaddition (32CA) reactions of C-cyclopropyl-N-methylnitrone 1 with styrene 2 have been studied within molecular electron density theory (MEDT) at the B3LYP/6-311++G(d,p) level theory. These zwitterionic type 32CA occur through a one-step mechanism. undergo four stereo- and regioisomeric reaction paths to form different products, 3, 4, 5 6. Analysis conceptual functional (CDFT) indices predict global electronic flux from strong nucleophilic nitrone 2. are endergonic Gibbs free energies between 2.83 7.39 kcal.mol-1 in gas phase. leading formation cycloadduct 3 presents lowest activation enthalpy than other due slightly increase polar character evident transfer (GEDT) transition states along path. bonding evolution (BET) study suggests that these coupling pseudoradical centers new C-C C-O covalent bonds has not started states.
 
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