Rationalizing the Regioselectivity of the Diels-Alder Biscycloaddition of Fullerenes

The Journal of Organic Chemistry
Yago García-RodejaIsrael Fernández

Abstract

The physical factors governing the regioselectivity of the double functionalization of fullerenes have been explored by means of density functional theory calculations. To this end, the second Diels-Alder cycloaddition reactions involving 1,3-butadiene and the parent C60 fullerene as well as the ion-encapsulated system Li+@C60 have been selected. In agreement with previous experimental findings on related processes, it is found that the cycloaddition reaction, involving either C60 or Li+@C60, occurs selectively at specific [6,6]-bonds. The combination of the activation strain model of reactivity and the energy decomposition analysis methods has been applied to gain a quantitative understanding into the markedly different reactivity of the available [6,6]-bonds leading to the observed regioselectivity in the transformation.

References

Sep 15, 1988·Physical Review A: General Physics·A D Becke
Jun 15, 1986·Physical Review. B, Condensed Matter·J P Perdew
Sep 15, 2005·Journal of the American Chemical Society·Steven StevensonJ Paige Phillips
May 17, 2006·Chemical Communications : Chem Comm·Nazario Martín
Oct 7, 2006·Journal of Molecular Modeling·Mariusz Mitoraj, Artur Michalak
Aug 10, 2007·Journal of the American Chemical Society·Daniel H Ess, K N Houk
Jul 11, 2008·Journal of the American Chemical Society·Daniel H Ess, K N Houk
May 23, 2009·Journal of the American Chemical Society·Franziska SchoenebeckK N Houk
Jul 10, 2009·Chemical Society Reviews·Dirk M GuldiNazario Martín
May 22, 2010·Organic & Biomolecular Chemistry·Willem-Jan van Zeist, F Matthias Bickelhaupt
Oct 16, 2010·Journal of Computational Chemistry·H ReisR Zaleśny
Apr 19, 2011·Journal of the American Chemical Society·Midori O IshitsukaShigeru Nagase
Oct 1, 2011·Journal of the American Chemical Society·Koji SawaiShigeru Nagase
Feb 7, 2013·Nature Communications·Jingbi YouYang Yang
Apr 11, 2013·Chemical Reviews·Manolis D Tzirakis, Michael Orfanopoulos
Apr 12, 2013·Chemistry : a European Journal·Israel FernándezF Matthias Bickelhaupt
Oct 18, 2013·Angewandte Chemie·Marta IzquierdoLuis Echegoyen
Jan 23, 2014·Journal of Computational Chemistry·Israel Fernández, F Matthias Bickelhaupt
Apr 5, 2014·Chemical Society Reviews·Israel Fernández, F Matthias Bickelhaupt
Nov 14, 2014·Chemistry, an Asian Journal·Yuki KawashimaShunichi Fukuzumi
Feb 26, 2015·The Journal of Physical Chemistry. a·Cheng-Xing Cui, Ya-Jun Liu
Apr 9, 2015·Chemistry : a European Journal·Maira R CerónLuis Echegoyen
Apr 15, 2015·Chemical Communications : Chem Comm·Kei OhkuboShunichi Fukuzumi
Apr 14, 2009·Journal of Chemical Theory and Computation·Mariusz P MitorajTom Ziegler
Dec 9, 2015·Chemistry : a European Journal·Yago García-RodejaIsrael Fernández
Jan 12, 2016·Wiley Interdisciplinary Reviews. Computational Molecular Science·Lando P Wolters, F Matthias Bickelhaupt
Jul 8, 2016·The Journal of Organic Chemistry·Yago García-Rodeja, Israel Fernández
Nov 15, 2016·Physical Chemistry Chemical Physics : PCCP·Hal SuzukiEunsang Kwon
Nov 20, 2016·Chemistry, an Asian Journal·Israel Fernández, F Matthias Bickelhaupt
Dec 16, 2016·The Journal of Organic Chemistry·Yago García-RodejaIsrael Fernández
Apr 28, 2017·Angewandte Chemie·F Matthias Bickelhaupt, Kendall N Houk
May 10, 2017·Chemistry : a European Journal·Yago García-RodejaIsrael Fernández
Nov 10, 2017·Physical Chemistry Chemical Physics : PCCP·Cheng-Xing CuiYu Lan

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Citations

Nov 2, 2018·Physical Chemistry Chemical Physics : PCCP·Yago García-RodejaIsrael Fernández
May 20, 2020·Organic & Biomolecular Chemistry·Radu A TalmazanMaren Podewitz
Dec 14, 2018·ChemistryOpen·Song YuF Matthias Bickelhaupt
Apr 3, 2021·Chemistry : a European Journal·Yoshifumi HashikawaYasujiro Murata

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