Solvation Effects Drive the Selectivity in Diels-Alder Reaction Under Hyperbaric Conditions - Archive ouverte HAL Access content directly
Journal Articles Chemical Communications Year : 2020

Solvation Effects Drive the Selectivity in Diels-Alder Reaction Under Hyperbaric Conditions

Abstract

High pressure effects on the Diels-Alder reaction in condensed phase are investigated by means of theoretical methods, employing advanced multiscale modeling approaches based on physically grounded models. The simulations reveal how the increase of pressure from 1 to 10000 atm does not affect the stability of the reaction products, modifying the kinetics of the process by lowering considerably the transition state energy. The reaction profile at high pressure remarkably differs from that at 1 atm,showing a submerged TS and a pre–TS structure lower in energy. The different solvation between endo and exo pre–TS is revealed as the driving force pushing the reaction toward a much higher preference for the endo product at high pressure.
Fichier principal
Vignette du fichier
2020_ChemCom_ChemRXiv.pdf (2.09 Mo) Télécharger le fichier
Origin : Files produced by the author(s)
Loading...

Dates and versions

hal-02504716 , version 1 (05-11-2020)

Identifiers

Cite

Daniele Loco, Riccardo Spezia, François Cartier, Isabelle Chataigner, Jean-Philip Piquemal. Solvation Effects Drive the Selectivity in Diels-Alder Reaction Under Hyperbaric Conditions. Chemical Communications, 2020, 56, pp.6632-6635. ⟨10.1039/D0CC01938K⟩. ⟨hal-02504716⟩
93 View
137 Download

Altmetric

Share

Gmail Facebook X LinkedIn More