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Title: Local aromaticity in naphtho-annelated fluoranthenes: Can the five-membered rings be more aromatic than the six-membered rings?
Authors: Radenkovic, Slavko
Tošović, Jelena
Đurđević Nikolić, Jelena
Journal: Journal of Physical Chemistry A
Issue Date: 21-May-2015
Abstract: © 2015 American Chemical Society. All Kekulé-structure-based theories predict that the central five-membered ring in fluoranthene and naphtho-annelated fluoranthenes is nonaromatic. In the present work, a detailed study of the local aromaticity in a series of naphtho-annelated fluoranthene derivatives was performed by means of the following aromaticity indices: the energy effect (ef), bond resonance energy (BRE), multicenter delocalization indices (MCI), harmonic oscillator model of aromaticity (HOMA) index, nucleus-independent chemical shifts (NICS), and ring current maps. It was found that, according to the ef, BRE, MCI, and HOMA values, the pentagonal rings in some naphtho-annelated fluoranthenes can be even more aromatic than some hexagonal rings in the respective molecules. The magnetic indices do not support the results obtained by the energetic, electron delocalization, and geometrical aromaticity indices.
Type: article
DOI: 10.1021/acs.jpca.5b01817
ISSN: 10895639
SCOPUS: 84930225215
Appears in Collections:Faculty of Science, Kragujevac

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