Radenković Slavko, Tošović Jelena, Đurđević Nikolić Jelena
Faculty of Science, University of Kragujevac, 12 Radoja Domanovića, 34000 Kragujevac, Serbia.
J Phys Chem A. 2015 May 21;119(20):4972-82. doi: 10.1021/acs.jpca.5b01817. Epub 2015 May 7.
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.
所有基于凯库勒结构的理论都预测，芴和萘并芴中的中心五元环是非芳香性的。在本工作中，通过以下芳香性指标对一系列萘并芴衍生物中的局部芳香性进行了详细研究：能量效应（ef）、键共振能（BRE）、多中心离域指数（MCI）、芳香性的谐振子模型（HOMA）指数、核独立化学位移（NICS）和环电流图。结果发现，根据ef、BRE、MCI和HOMA值，某些萘并芴中的五元环比相应分子中的一些六元环更具芳香性。磁性指标不支持由能量、电子离域和几何芳香性指标获得的结果。
