期刊
JOURNAL OF CHEMICAL INFORMATION AND MODELING
卷 49, 期 2, 页码 369-376出版社
AMER CHEMICAL SOC
DOI: 10.1021/ci800400b
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A topological index of reactivity (TIR) of benzenoid hydrocarbons is defined basing on an approximate value of the bicentric localization energies. TIR values correlate with all known (24) Hammett-Streitwieser position constants, based on kinetic data for electrophilic substitution in benzenoid hydrocarbons. The maximum value of the index, denoted by TIR(max), defines the stability of a molecule toward electrophiles. For all 35 nonisoarithmic molecules of benzenoid hydrocarbons for which Hess and Schaad data are known, TIR(max) values correlate with classical numerical characteristics of aromaticity: resonance energy per pi-electron (REPE), HOMO-LUMO gap, and geometry based aromaticity index HOMA. Correlation between TIR(max) and exaltation of magnetic susceptibility is also found for cata-condensed benzenoid hydrocarbons, whereas if the peri-condensed ones are included, no correlation is observed. This can be ascribed to the presence of both paratropic and diatropic rings in perifusenes.
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