NMR Study of Hyperporphyrin Effects in the Protonations of Porphyrins with 4-Aminophenyl and 4-Pyridyl Meso Substituents
Sponsor
Support from the Oregon Nanoscience and Microtechnologies Institute (ONAMI) and the National Science Foundation (Grant CHE-0911186) is gratefully acknowledged.
Published In
The Journal of Organic Chemistry
Document Type
Citation
Publication Date
2015
Abstract
Titrations for a series of porphyrins bearing either 4-aminophenyl or 4-pyridyl meso substituents were performed using methanesulfonic acid in DMSO and followed by proton NMR. Special emphasis was placed on identifying the intermediate protonation stages that are described as hyperporphyrins, that is, where there exist strong charge-transfer interactions between the peripheral aminophenyl groups and the protonated porphyrin ring. In particular, evidence was gathered to support the significance of a novel resonance form involving charge transfer between two peripheral substituents, an aminophenyl group and a protonated pyridinium group. 1H NMR and NOESY spectra provide evidence for the importance of such resonance effects in the triply protonated triamino/monopyridyl hyperporphyrin (A3PyPH3+3).
Rights
Copyright © 2022
American Chemical Society
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DOI
10.1021/acs.joc.5b00690
Persistent Identifier
https://archives.pdx.edu/ds/psu/38288
Citation Details
Wang, C., & Wamser, C. C. (2015). NMR Study of Hyperporphyrin Effects in the Protonations of Porphyrins with 4-Aminophenyl and 4-Pyridyl Meso Substituents. The Journal of Organic Chemistry, 80(15), 7351-7359.