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Structure, Bonding and Reactivity of Heterocyclic Compounds pp 129–160Cite as

Aromaticity of Organic and Inorganic Heterocycles

Part of the Topics in Heterocyclic Chemistry book series (TOPICS,volume 38)

Abstract

Heteroaromatic rings are present in many organic molecules. They can be found as part of the core of drugs or agrochemicals and in many important biochemical molecules. The last three centuries have brought important advances in heteroaromatic chemistry. Indeed, the first organic molecules with heteroaromatic rings were already synthesized in the middle of the nineteenth century. Then, the twentieth century witnessed the first inorganic heteroaromatic compound produced in the laboratory. And at the beginning of the present century, the first all-metal heteroaromatic cluster was detected. Here, we discuss the aromaticity of some of these heteroaromatic compounds using different descriptors of aromaticity, with special emphasis in those measures based on electron delocalization properties of the aromatic rings.

Keywords

  • Aromaticity
  • Heteroaromaticity
  • Nucleus-independent chemical shifts
  • Electronic indices
  • Multicenter electronic indices
  • Harmonic oscillator model of aromaticity
  • Aromatic fluctuation index
  • Para delocalization index

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Acknowledgments

The following organizations are thanked for financial support: the Ministerio de Ciencia e Innovación (MICINN, project numbers CTQ2011-23156/BQU and CTQ2011-25086/BQU), the Generalitat de Catalunya (project numbers 2009SGR637 and 2014SGR931 and Xarxa de Referència en Química Teòrica i Computacional), and the FEDER fund (European Fund for Regional Development) for the grant UNGI08-4E-003. Excellent service by the Centre de Serveis Científics i Acadèmics de Catalunya (CESCA) is gratefully acknowledged. Support for the research of M. Solà was received through the ICREA Academia 2009 prize for excellence in research funded by the DIUE of the Generalitat de Catalunya. E.M. acknowledges financial support of the EU under the Marie Curie Career Integration grant (PCI09-GA-2011-294240) and the Beatriu de Pinós program from AGAUR for the postdoctoral grant (BP_B_00236). F.F acknowledges financial support from AGAUR for the Beatriu de Pinós postdoctoral Grant (BP_A_00339).

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Authors and Affiliations

  1. Department of Pharmacology, University of California, San Diego, La Jolla, CA, USA

    Ferran Feixas

  2. Institut de Química Computacional i Catàlisi (IQCC) and Departament de Química, Universitat de Girona, Campus de Montilivi, Girona, Catalonia, Spain

    Jordi Poater, Eduard Matito & Miquel Solà

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  1. Ferran Feixas
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  2. Jordi Poater
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  3. Eduard Matito
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  4. Miquel Solà
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Correspondence to Miquel Solà .

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Editors and Affiliations

  1. Research Group of General Chemistry, Vrije Universiteit Brussel (VUB), Brussels, Belgium

    Frank De Proft

  2. Research Group of General Chemistry, Vrije Universiteit Brussel (VUB), Brussels, Belgium

    Paul Geerlings

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Feixas, F., Poater, J., Matito, E., Solà, M. (2014). Aromaticity of Organic and Inorganic Heterocycles. In: De Proft, F., Geerlings, P. (eds) Structure, Bonding and Reactivity of Heterocyclic Compounds. Topics in Heterocyclic Chemistry, vol 38. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-45149-2_5

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