Quantum Tunneling Instability in Pericyclic Reactions: The Cheletropic, Coarctate, and Ene Cases

Alexander Frenklach; Hila Amlani; Sebastian Kozuch

doi:https://doi.org/10.1021/acs.orglett.4c01635

Quantum Tunneling Instability in Pericyclic Reactions: The Cheletropic, Coarctate, and Ene Cases

Alexander Frenklach, Hila Amlani, Sebastian Kozuch

Department of Chemistry

Ben-Gurion University of the Negev

Research output: Contribution to journal › Article › peer-review

Abstract

Some retro-pericyclic reactions, as a result of their high exothermicity and short trajectories, are the perfect ground for heavy atom tunneling molecular decompositions, also known as “quantum tunneling instability” (QTI). Considering this effect, in our first installment [ Frenklach, A. ; Amlani, H. ; Kozuch, S. Quantum Tunneling Instability in Pericyclic Reactions. J. Am. Chem. Soc. 2024, 146 (17), 11823−11834, DOI: 10.1021/jacs.4c00608], we computed several retro-Diels-Alder reactions, predicting that many studied reactants cannot be isolated. Herein, we will explore the QTI of retro-cheletropic, coarctate, and ene exemplars, where again we hypothesize the impossibility to detect their reactants.

Original language	American English
Pages (from-to)	5157-5161
Number of pages	5
Journal	Organic Letters
Volume	26
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.4c01635
State	Published - 21 Jun 2024

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "Some retro-pericyclic reactions, as a result of their high exothermicity and short trajectories, are the perfect ground for heavy atom tunneling molecular decompositions, also known as “quantum tunneling instability” (QTI). Considering this effect, in our first installment [ Frenklach, A. ; Amlani, H. ; Kozuch, S. Quantum Tunneling Instability in Pericyclic Reactions. J. Am. Chem. Soc. 2024, 146 (17), 11823−11834, DOI: 10.1021/jacs.4c00608], we computed several retro-Diels-Alder reactions, predicting that many studied reactants cannot be isolated. Herein, we will explore the QTI of retro-cheletropic, coarctate, and ene exemplars, where again we hypothesize the impossibility to detect their reactants.",

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Quantum Tunneling Instability in Pericyclic Reactions: The Cheletropic, Coarctate, and Ene Cases

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