pp 1-71 | Cite as

Aromaticity and Tautomerism in Porphyrins and Porphyrinoids

  • M.  Ste˛pień
  • L.  Latos-Graz.yński
Chapter
Part of the Topics in Heterocyclic Chemistry book series

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.

Keywords

Aromaticity Electronic structure NMR spectroscopy Porphyrinoids Tautomerism 

Notes

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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Copyright information

© Springer-Verlag 2008

Authors and Affiliations

  • M.  Ste˛pień
    • 1
  • L.  Latos-Graz.yński
    • 1
  1. 1.Wydział ChemiiUniwersytet WrocławskiPoland

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