Electronic nature of the aromatic adamantanediyl ions and its analogues

Journal of the Brazilian Chemical Society

Caio L. Firme¹  O. A. C. Antunes¹  Pierre M. Esteves¹ 

[1] ,Universidade Federal do Rio de Janeiro Instituto de Química Rio de Janeiro RJ ,Brazil

关键词: adamantyl dication;    adamantyl cation;    degeneracy;    delocalization index;    ring density;    aromaticity;    tridimensional aromaticity;    1;    3-dehydro-5;    7-adamantanediyl dication;   

DOI  :  10.1590/S0103-50532008000100020

来源: SciELO

【 摘 要 】

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.

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