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Aromaticity and Tautomerism in Porphyrins and Porphyrinoids

  • Chapter
Aromaticity in Heterocyclic Compounds

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 19))

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

    M Stępień & L. Latos-Grażyński

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  1. Department of Chemistry, University of Warsaw, ul. Pasteura 1, Warszawa, 02-093, Poland

    Tadeusz M. Krygowski  & Michał K. Cyrański  & 

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Stępień, M., Latos-Grażyński, L. (2009). Aromaticity and Tautomerism in Porphyrins and Porphyrinoids. In: Krygowski, T.M., Cyrański, M.K. (eds) Aromaticity in Heterocyclic Compounds. Topics in Heterocyclic Chemistry, vol 19. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-68343-8_3

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