Phenyl-cyclopentadienyl rule

Authors

  • Jelena Đurđević Faculty of Science, University of Kragujevac, P. O. Box 60, 34000 Kragujevac
  • Ivan Gutman Faculty of Science, University of Kragujevac, P. O. Box 60, 34000 Kragujevac

DOI:

https://doi.org/10.20450/mjcce.2012.52

Keywords:

polycyclic aromatic hydrocarbons, cyclic conjugation, energy effect of cyclic conjugation, acenaphthylene, fluoranthene, DFT, multicenter bond indices, ring currents, NICS

Abstract

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).

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Published

2012-06-15

How to Cite

Đurđević, J., & Gutman, I. (2012). Phenyl-cyclopentadienyl rule. Macedonian Journal of Chemistry and Chemical Engineering, 31(1), 1–15. https://doi.org/10.20450/mjcce.2012.52

Issue

Vol. 31 No. 1 (2012)

Section

Theoretical Chemistry

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