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A estabilidade relativa do dication 1,3-desidro-5,7-adamantanediila e atribuida a sua aromaticidade tridimensional. Contudo, sua natureza eletronica nao e bem conhecida. A fim de entende-la melhor, os di- e monocations do adamantanodiil e alguns de seus analogos foram estudados utilizando a teoria de atomos e moleculas (AIM). Eles foram comparados com analogos de adamantano nao-aromaticos. Os resultados de AIM indicam que a densidade eletronica no centro da estrutura em gaiola e a media de todos os indices de deslocalizacao, envolvendo seus atomos cabecas-de-ponte sao maiores em compostos aromaticos do que em nao-aromaticos. A degenerescencia energetica dos atomos cabeca-de-ponte, a uniformidade e magnitude da carga compartilhada entre estes, distingue os dications 1,3-adamantila e 1,3-desidro-5,7-adamantanediila. Contudo, ambos sao aromaticos, assim como o 1,3-desidro-5,7-diboroadamantano. O cation 1,3-desidro-7-adamantila tem uma homoaromaticidade planar caracteristica. The relative stability of the 1,3-dehydro-5,7-adamantanediyl dication is ascribed to its tridimensional aromaticity. However, its electronic nature is not well known. In order to improve its understanding, dicationic and monocationic adamantanedyil species and some key analogues were studied by atoms in molecules (AIM) theory. They were compared to non-aromatic adamantane analogues. AIM results indicate that the density in center of the cage structure and the average of all delocalization indexes involving its bridged atoms are higher in aromatic than in non-aromatic compounds. Degeneracy in energy of the bridged atoms, uniformity and magnitude of their shared charge distinguish the dications 1,3-adamantyl and the 1,3-dehydro-5,7-adamantanediyl. However, both are aromatic as well as the 1,3-dehydro-5,7-diboroadamantane. The 1,3-dehydro-7-adamantyl cation has a characteristic planar homoaromaticity.

Electronic nature of the aromatic adamantanediyl ions and its analogues