Abstract

VIVAS-REYES, R; CARDOZO, K. M  and  OVIEDO, J. F. A Diels-Alder Reaction Theoretical Study, by using Quiral Anthracene Groups, Through the Frontier Orbitals Usage. Ciencia en Desarrollo [online]. 2014, vol.5, n.2, pp.107-116. ISSN 0121-7488.

A theoretical calculation' series was applied to a reaction of Diels-Alder, in which some series of quiral anthracene groups and dienofilos derived from the maleic anhydride and maleimides were used. The calculations were carried out in the program Gaussian 98 using the functional B3LYP along with the base 3-21G*. The energy of the frontier orbitals was analyzed, and it was possible to conclude that the reaction was the type Diels-Alder of normal demand of electrons, which is useful to increase the reactivity when a diene is bonded to a substituent donator of electrons, because in this way the energy of orbitals HOMO-LUMO increases, and when the dienofiles were bonded to a substituent that attracts electrons, the energy of the orbitals HOMO-LUMO decreases. With respect to the orbital geometry of the frontier orbitals was found that stereo selectivity in the reaction was a guide under the conservation principle of the orbital symmetry.

Keywords : DFT; Diels-Alder Reactions; Frontier Orbitals; HOMO; LUMO.

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