Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 23, Pages 8213-8223Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo101856h
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Funding
- Ministry of Education, Culture, Sports, Science and Technology of Japan
- [21750047]
- [21108518]
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Conformations and electronic states of Huckel-aromatic regular, singly, doubly, and triply N-confused [26]hexaphyrins were investigated using density functional theory (DFT) calculations. A comparison of the molecular energies of 754 structures in all revealed that the most stable conformers depend on the degree of confusion, where ring strain and intramolecular hydrogen bonding would play a critical role. Consequently, regular and singly N-confused hexaphyrins prefer a dumbbell conformation, doubly N-confused hexaphyrin prefers a rectangular conformation, and triply N-confused hexaphyrin prefers a triangular conformation. Introduction of N-confused pyrrole rings into the hexaphyrin framework causes narrower HOMO-LUMO energy gaps, while it does not affect the NICS values or aromaticity significantly. The steric repulsion imposed by meso-aryl substituents largely affects the relative energies among the conformers.
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