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Molecules 2016, 21(2), 200;

The Diels-Alder Cycloaddition Reaction of Substituted Hemifullerenes with 1,3-Butadiene: Effect of Electron-Donating and Electron-Withdrawing Substituents

Departamento de Química, División de Ciencias Básicas e Ingeniería, Universidad Autónoma Metropolitana-Iztapalapa, 09340 México D. F., Mexico
Departamento de Física Teórica, Atómica y Óptica, Universidad de Valladolid, 47011 Valladolid, Spain
Author to whom correspondence should be addressed.
Received: 12 December 2015 / Revised: 27 January 2016 / Accepted: 31 January 2016 / Published: 12 February 2016
(This article belongs to the Special Issue Fullerene and the Related Curved-pi Materials Chemistry)
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The Diels-Alder (DA) reaction provides an attractive route to increase the number of six member rings in substituted Polycyclic Aromatic Hydrocarbons (PAHs). The density functional theory (DFT) B3LYP method has been used in this work to inquire if the substitution of H over the edge of triindenetriphenylene (pristine hemifullerene 1) and pentacyclopentacorannulene (pristine hemifullerene 2), could improve the DA cycloaddition reaction with 1,3-butadiene. The substituents tested include electron-donating (NH2, OMe, OH, Me, i-Pr) and electron-withdrawing groups (F, COOH, CF3, CHO, CN, NO2). The electronic, kinetic and thermodynamic parameters of the DA reactions of the substituted hemifullerenes with 1,3-butadiene have been analyzed. The most promising results were obtained for the NO2 substituent; the activation energy barriers for reactions using this substituent were lower than the barriers for the pristine hemifullerenes. This leads us to expect that the cycloadditions to a starting fullerene fragment will be possible. View Full-Text
Keywords: Diels-Alder; DFT; polycyclic aromatic hydrocarbons (PAHs) Diels-Alder; DFT; polycyclic aromatic hydrocarbons (PAHs)

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Mojica, M.; Méndez, F.; Alonso, J.A. The Diels-Alder Cycloaddition Reaction of Substituted Hemifullerenes with 1,3-Butadiene: Effect of Electron-Donating and Electron-Withdrawing Substituents. Molecules 2016, 21, 200.

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