RT info:eu-repo/semantics/article
T1 The diels-alder cycloaddition reaction of substituted hemifullerenes with 1,3-butadiene: Effect of electron-donating and electron-withdrawing substituents
A1 Mojica, Martha
A1 Méndez, Francisco
A1 Alonso Martín, Julio Alfonso
K1 Diels-Alder
K1 DFT
K1 Polycyclic Aromatic Hydrocarbons (PAHs)
K1 22 Física
AB 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.
PB MDPI
YR 2016
FD 2016
LK https://uvadoc.uva.es/handle/10324/57376
UL https://uvadoc.uva.es/handle/10324/57376
LA eng
NO Molecules, 2016, vol. 21, n. 2, p. 200
NO Producción Científica
DS UVaDOC
RD 17-jul-2024