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Aromatic character of O h ‐C 24 N 24 . A cavernous nitride fullerene bearing N 4 ‐macrocycle motifs
Author(s) -
Charistos Nickolas D.,
Jin Peng,
MuñozCastro Alvaro
Publication year - 2019
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.25919
Subject(s) - antiaromaticity , aromaticity , fullerene , chemistry , crystallography , computational chemistry , chemical physics , organic chemistry , molecule
Spherical fullerenes offer noteworthy structures usually involving six‐ and five‐membered faces, with application in technological issues. In this sense, cavernous spherical‐like structures bearing larger holes provide interesting examples for further understanding of structure‐properties relationship. Here, we explored the magnetic response of a proposed cavernous nitride fullerene, C 24 N 24 , which has a O h ‐symmetry with six N 4 ‐macrocyclic and eight 1,3,5‐triazine faces displaying 48‐π electrons. C 24 N 24 exhibits a local aromatic behavior owing to the contrasting antiaromatic response of the N 4 ‐macrocyclic faces and the aromatic character of the 1,3,5‐triazine faces. Thus, the overall structure is ascribed as a local aromatic species, where the triazine faces exhibit the characteristic shielding cone for aromatic rings. Furthermore, the constructive combination of local shielding cones in C 24 N 24 delivers a related shielding‐cone response, as expected for a perfect aromatic cage. Hence, the local aromatic/nonaromatic/antiaromatic sections exhibit an additive or subtractive interaction, leading to a characteristic response inherent to the nature of the spherical cage. We expect that further study of the interplay between different aromatic and antiaromatic faces in fullerene‐like cages can deliver interesting pseudo‐aromatic or pseudo‐antiaromatic spherical species.