Why Are the Kinked Polyacenes More Stable than the Straight Ones? A Topological Study and Introduction of a New Topological Index of Aromaticity

Why Are the Kinked Polyacenes More Stable than the Straight Ones? A Topological Study and Introduction of a New Topological Index of Aromaticity

A topological model for estimating the stability of benzenoid hydrocarbons (BHs) is presented showing an acceptable linear dependence on Hess−Schaad resonance energy per π-electron values. The topological measure of stability is accessible by use of pencil calculation and is based on counting cis-ty...

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Veröffentlicht in:Journal of Chemical Information and Modeling 2008-07, Vol.48 (7), p.1358-1366
Hauptverfasser: Ciesielski, Arkadiusz, Krygowski, Tadeusz M, Cyrański, Michał K
Format: Artikel
Sprache:eng
Schlagworte:
Chemical Information
Chemicals
Hydrocarbons
Information storage
Information systems
Molecular Structure
Polycyclic Compounds - chemistry
Topology
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Zusammenfassung:A topological model for estimating the stability of benzenoid hydrocarbons (BHs) is presented showing an acceptable linear dependence on Hess−Schaad resonance energy per π-electron values. The topological measure of stability is accessible by use of pencil calculation and is based on counting cis-type fragments of double bonds in all canonical structures of a given BH. Evidence is given that infinite chains of straight linear polyacenes are always less stable than the kinked ones.
ISSN:1549-9596
1520-5142
1549-960X
DOI:10.1021/ci800061q