Journal
JOURNAL OF PHYSICAL CHEMISTRY A
Volume 112, Issue 23, Pages 5305-5311Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jp8014996
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Macrocyclic aromaticity is the most important concept in porphyrinoid chemistry. Bond resonance energy (BRE) for any pi-bond linking adjacent pyrrolic or other rings represents the stabilization energy due to macrocyclic aromaticity. We found that a main conjugation pathway associated with macrocyclic aromaticity can be traced by choosing a pi-bond with a larger BRE, at every bifurcation of the pi-network. All pi-bonds located along the main conjugation pathway are intensified with large positive BREs compared with those located along the bypasses. On the other hand, a main destabilization pathway associated with macrocyclic antiaromaticity can be traced by choosing a pi-bond with a smaller BRE at every bifurcation of the pi-network, Macrocyclic conjugation pathways thus determined are fully consistent with the chemical shifts of protons attached to the macrocycle.
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