Macedonian Journal of Chemistry and Chemical Engineering | |
Phenyl-cyclopentadienyl rule | |
Jelena Đurđević1  Ivan Gutman1  | |
[1] Faculty of Science, University of Kragujevac, P. O. Box 60, 34000 Kragujevac; | |
关键词: polycyclic aromatic hydrocarbons; cyclic conjugation; energy effect of cyclic conjugation; acenaphthylene; fluoranthene; dft; multicenter bond indices; ring currents; nics; | |
DOI : 10.20450/mjcce.2012.52 | |
来源: DOAJ |
【 摘 要 】
Within a systematic study of cyclic conjugation in the benzo-annelated derivatives of acenaphthylene and fluoranthene, a general regularity was discovered, named phenyl-cyclopentadienyl rule (PCP rule). According to this rule, six-membered rings connected to the five-membered ring by a single carbon-carbon bond increase the magnitude of cyclic conjugation in the five-membered ring. The greater the number of such six-membered rings is, the stronger the cyclic conjugation in the five-membered ring. The PCP rule was initially established by studying the energy effects of individual rings, and was eventually corroborated by a variety of other independent approaches (Wiberg bond orders, carbon-carbon bond lengths calculated by high-level ab initio DFT methods, multicenter delocalization indices, ring currents).
【 授权许可】
Unknown