Density, degeneracy, delocalization-based index of aromaticity (D3BIA)

Journal of the Brazilian Chemical Society

Firme, Caio L.¹  Universidade de São Paulo, Ribeirão Preto, Brazil¹  Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil¹  Antunes, O. A. C.¹  Galembeck, Sergio E.¹  Esteves, Pierre M.¹ 

关键词: delocalization index;    degeneracy;    ring density;    aromaticity;   

DOI  :  10.1590/S0103-50532007000700016

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

Aromaticity has been exhaustedly discussed for several years and it remains as a misterious issue. In this work it is proposed a new index of aromaticity named density, degeneracy and delocalization-based index of aromaticity or simply D3BIA in an attempt to cast new insight and perspective over this theme. This index is based on AIM (atoms in molecules) theory and it is somewhat supported by SC (spin-coupled) theory. Aromaticity decreases as the number of heteroatoms in the aromatic molecule increases since degeneracy decreases and it decreases as the ring size of an aromatic compound increases because it disfavors overlap of single-electron states. The relation between planar structures, electron density and aromaticity is also observed. The attractive interaction of 6p-electron resonance in cyclobutadiene dianion compensate its carbon-to-carbon repulsive interaction while in its dicationic parent the 2p-electron resonance is insufficient to counterbalance its carbon-to-carbon repulsive interaction and it adopts a puckered structure.

【 授权许可】

Unknown