The Acenes:  Is There a Relationship between Aromatic Stabilization and Reactivity?

Despite the increasing reactivity from benzene to heptacene, the acene resonance energies per π electron are nearly constant. The reactivities (computed activation energies) of the individual acene rings correlate with the reaction energies and depend on the product stabilities. Nucleus-independent...

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Bibliographic Details
Published in:Organic letters 2001-11, Vol.3 (23), p.3643-3646
Main Authors: Schleyer, Paul von Ragué, Manoharan, Mariappan, Jiao, Haijun, Stahl, Frank
Format: Article
Language:English
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Summary:Despite the increasing reactivity from benzene to heptacene, the acene resonance energies per π electron are nearly constant. The reactivities (computed activation energies) of the individual acene rings correlate with the reaction energies and depend on the product stabilities. Nucleus-independent chemical shifts (NICS; note the sizes of the red dots, above) indicate that the more reactive inner rings actually are more aromatic than the less reactive outer rings and even more aromatic than benzene itself.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol016553b