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Journal of Molecular Modeling

, Volume 19, Issue 9, pp 3529–3535 | Cite as

A comparative study of the aromaticity of pyrrole, furan, thiophene, and their aza-derivatives

  • Kalbinur Najmidin
  • Ablikim KerimEmail author
  • Paruza Abdirishit
  • Horigul Kalam
  • Tursungul Tawar
Original Paper

Abstract

The relative aromaticity of pyrrole, furan, thiophene, and their aza-derivatives has been examined using TRE (topological resonance energy), MRE (magnetic resonance energy), ring current (RC), and ring current diamagnetic susceptibility (χG) methods. The results obtained were compared with results obtained by others who used the energetic method ASE (aromatic stabilization energy), the geometric method HOMA (harmonic oscillator model of aromaticity), and the magnetic method NICS(1) (nucleus-independent chemical shift). The impact of nitrogen atoms on the aromaticity of the aza-derivatives of pyrrole, furan, and thiophene is discussed. An excellent correlation was found between the energetic (TRE, MRE) and magnetic (RC and χG) criteria of aromaticity for all compounds. It was expected that inclusion of a heteroatom would decrease the aromaticity relative to the cyclopentadienyl anion. Our results show that the type of the first heteroatom, which donates two electrons to the system, as well as the number of nitrogen atoms and their positions in the molecule have a strong effect on aromaticity. In general, aromaticity is enhanced when the nitrogen atom is adjacent to the first heteroatom. The magnitude of aromaticity is related closely with the uniformity of distribution of π-electrons in the molecule.

Keywords

Aromaticity Azoles Diatropicity Resonance energy NICS(1) 

Notes

Acknowledgments

This work was supported financially by the Natural Science Foundation of China (No. 21262037), and by the Urumqi Science and Technology Project (No. H101133001) of the Xinjiang Uyghur Autonomous Region, China.

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Copyright information

© Springer-Verlag Berlin Heidelberg 2013

Authors and Affiliations

  • Kalbinur Najmidin
    • 1
  • Ablikim Kerim
    • 1
    Email author
  • Paruza Abdirishit
    • 1
  • Horigul Kalam
    • 1
  • Tursungul Tawar
    • 1
  1. 1.Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, School of Chemistry and Chemical EngineeringXinjiang UniversityUrumqiChina

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