On the Notation of Catastrophes in the Framework of Bonding Evolution Theory: Case of Normal and Inverse Electron Demand Diels-Alder Reactions

Leandro Ayarde-Henríquez, Cristian Guerra, Mario Duque-Noreña, Elizabeth Rincón, Patricia Pérez, Eduardo Chamorro

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

This paper generalizes very recent and unexpected findings [J. Phys. Chem. A, 2021, 125, 5152–5165] regarding the known “direct- and inverse-electron demand” Diels-Alder mechanisms. Application of bonding evolution theory indicates that the key electron rearrangement associated with significant chemical events (e. g., the breaking/forming processes of bonds) can be characterized via the simplest fold polynomial. For the CC bond formation, neither substituent position nor the type of electronic demand induces a measurable cusp-type signature. As opposed to the case of [4+2] cycloaddition between 1,3-butadiene and ethylene, where the two new CC single bonds occur beyond the transition state (TS) in the activated cases, the first CC bond occurs in the domain of structural stability featuring the TS, whereas the second one remains located in the deactivation path connecting the TS with the cycloadduct.

Original languageEnglish
JournalChemPhysChem
DOIs
Publication statusAccepted/In press - 2022

Keywords

  • Bonding evolution theory
  • Diels-Alder reactions
  • nonconcerted reaction mechanisms
  • normal and inverse electron demands
  • pericyclic reactions

ASJC Scopus subject areas

  • Atomic and Molecular Physics, and Optics
  • Physical and Theoretical Chemistry

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