Aromaticity of Heterofullerenes C₁₈B_xN_y (x+y=2) and Their Molecular Ions

The aromaticity of all possible substituted fullerene isomers of C18N2, C18B2, C18BN, and their molecularions which originate from the C20 (Ih) cage were studied by the topological resonance energy (TRE) and the percentage topological resonance energy methods. The relationship between the aromaticity of C18BxNy isomers and the sites where the heteroatoms dope at the C20 (Ih) cage is discussed. Calculation results show that at the neutral and cationic states all the isomers are predicted to be antiaromatic with negative TREs, but their polyvalent anions are predicted to be aromatic with positive TREs. The most stable isomer is formed by heteroatom doping at the 1,11-sites in C18N2, C18B2, and C18BN. Heterofullerenes are more aromatic than C20. The stability order in the neutral states is C18N2>C18BN>C18B2>C20. The stability order in closed-shell is C18B2 8->C20 6->C18BN6->C18N2 4-. This predicts theoretically that their polyvalent anions have high aromaticity.