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Bond resonance energy and verification of the isolated pentagon rule

Journal Article · · Journal of the American Chemical Society

The isolated pentagon rule (IPR) states that fullerenes with isolated pentagons are kinetically much more stable than their fused pentagon counterparts. This rule can be verified in terms of a graph-theoretically defined bond resonance energy. In general, a {pi} bond shared by two pentagons has a large negative bond resonance energy, thus contributing significantly to the increase in kinetic instability or chemical reactivity of the molecule. The existence of such highly antiaromatic local structures sharply distinguishes IPR-violating fullerenes from isolated-pentagon isomers. {pi}bonds shared by two pentagons are shared by many antiaromatic conjugated circuits but not by relatively small aromatic conjugated circuits. 39 refs., 3 figs., 5 tabs.

Sponsoring Organization:
USDOE
OSTI ID:
41832
Journal Information:
Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 14 Vol. 117; ISSN JACSAT; ISSN 0002-7863
Country of Publication:
United States
Language:
English

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