Prediction of extended aromaticity for a novel C(48)N(12) azafullerene structure

M Riad Manaa; David W Sprehn; Heather A Ichord

doi:10.1021/ja0281885

Prediction of extended aromaticity for a novel C(48)N(12) azafullerene structure

J Am Chem Soc. 2002 Nov 27;124(47):13990-1. doi: 10.1021/ja0281885.

Authors

M Riad Manaa¹, David W Sprehn, Heather A Ichord

Affiliation

¹ Lawrence Livermore National Laboratory, Energetic Materials Center, University of California, P.O. Box 808, L-282, Livermore, CA 94551, USA.

PMID: 12440886
DOI: 10.1021/ja0281885

Abstract

We report the existence of a novel C48N12 molecular structure to the recently reported thin-film formation of nano-onions of carbon and nitrogen with similar composition [Phys. Rev. Lett. 2001, 87, 225503]. An extended local aromaticity of eight all-carbon hexagonal rings is the driving force toward the maximum stability of this molecule, which is found to be 13.1 kcal/mol energetically more stable at the B3LYP/6-31G* level of theory than the recently reported structure [Chem. Phys. Lett. 2001, 340, 227]. The extended region of electron delocalization enhances the stability of this molecule via resonance energy contribution. On the basis of HUMO-LUMO gap of 2.74 eV, the new material is predicted to be an insulator.