Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/79813
Type: Artigo de periódico
Title: Revisiting the Stability of endo/exo Diels-Alder Adducts between Cyclopentadiene and 1,4-benzoquinone
Author: Tormena, CF
Lacerda, V
de Oliveira, KT
Abstract: In this work it is presented a detailed theoretical analysis of the relative stability of endo/exo Diels-Alder adducts formed by the reaction between cyclopentadiene (1) and 1,4-benzoquinone (2). The intrinsic reaction coordinate (IRC) showed the existence of only one transition state for the reaction studied, for both endo 3 and exo 4 adducts. The energies of both adducts were obtained at high level of theory (CBS-Q) confirming that the endo adduct is more stable than exo, which is in the opposite way to the observed in reactions that usually follow Alder's rule. An electronic structure analysis was performed through NBO methodology, indicating that the attractive delocalization interaction predominates over the steric repulsive interaction in the endo adducts. In summary, for the studied cycloaddition reaction the endo adduct is the thermodynamic and kinetic product, which can be also confirmed by experimental data mentioned in this work.
Subject: Diels-Alder reaction
endo/exo stability
theoretical calculation
NBO analysis
Country: Brasil
Editor: Soc Brasileira Quimica
Rights: aberto
Identifier DOI: 10.1590/S0103-50532010000100017
Date Issue: 2010
Appears in Collections:Unicamp - Artigos e Outros Documentos

Files in This Item:
File Description SizeFormat 
WOS000275106400016.pdf768.81 kBAdobe PDFView/Open


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.