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Aromaticity and Tautomerism in Porphyrins and Porphyrinoids

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Topics in Heterocyclic Chemistry

Part of the book series: Topics in Heterocyclic Chemistry

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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  1. Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383 , Wrocław, , Poland

    M. Ste˛pień & L. Latos-Graz.yński

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  1. M. Ste˛pień
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Appendix

Appendix

Table 3 1H NMR shift data and UV–vis data for selected porphyrins and porphyrinoids
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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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