Abstract
Porphyrins and their analogues constitute one of the most important families of aromatic macrocycles. The present review discusses aromaticity of porphyrinoids, focusing mainly on non-expanded systems. The effect of structural modifications on the aromaticity-dependent properties of porphyrin-like macrocycles is described. It is shown that delocalization modes observed in porphyrinoids can be classified using a simple valence-bond approach. Aromaticity of porphyrinoids is further discussed as a function of tautomerism, coordination chemistry, and the oxidation state of the macrocycle.
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Acknowledgements
Financial support from the Ministry of Science and Higher Education (Grant PBZ-KBN-118/T09/2004) is kindly acknowledged. We thank Dr. Ludmiła Szterenberg for performing the DFT calculations cited in Table 1 and Dr. Natasza Sprutta for reading the manuscript and helpful comments.
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Ste˛pień, M., Latos-Graz.yński, L. (2008). Aromaticity and Tautomerism in Porphyrins and Porphyrinoids. In: Topics in Heterocyclic Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2008_4
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