22-Hydroxybenziporphyrin: Switching of Antiaromaticity by Phenol-Keto Tautomerization
|Marcin Stępień , Lechosław Latos-Grażyński , Ludmiła Szterenberg|
University of Wrocław, Faculty of Chemistry, Joliot-Curie 14, Wrocław 50-383, Poland
Benziporphyrins constitute a class of porphyrin analogs in which one of the pyrrole rings is replaced with a benzene ring . The aromaticity of these molecules depends on their topology [2, 3], tautomerism [4, 5], and coordination chemistry . Here we will describe 22-hydroxybenziporphyrin 1, which has been shown to exist as an equilibrium mixture of the 6-π electron phenolic tautomer 1 and the 20-π electron keto form 2. Aromaticity and tautomerism of these two forms has been probed with proton NMR spectroscopy and DFT calculations.
 M. Stępień, L. Latos-Grażyński, Acc. Chem. Res. 2005, 38, 88-98.
Presentation: oral at 18th Conference on Physical Organic Chemistry, Symposium 1, by Marcin Stępień
See On-line Journal of 18th Conference on Physical Organic Chemistry
Submitted: 2006-05-30 20:17 Revised: 2009-06-07 00:44