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Möbius bis and tris-spiroaromatic systems.

David Hall1, Henry S Rzepa

  • 1Department of Chemistry, Imperial College London, UK SW7 2AY.

Organic & Biomolecular Chemistry
|August 22, 2003
PubMed
Summary

Bis and tris-spiro 7-membered ring systems can be viewed as spiroaromatic molecules. Their Möbius aromaticity increases with specific spiro-atoms, confirmed by ab initio calculations.

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Area of Science:

  • Organic Chemistry
  • Theoretical Chemistry
  • Materials Science

Background:

  • Bis and tris-spiro 7-membered ring systems are known structures.
  • Their electronic properties, particularly aromaticity, are not fully understood.

Purpose of the Study:

  • To propose a new classification for these spirocyclic systems as spiroaromatic molecules.
  • To investigate the influence of the central spiro-atom (X) on their Möbius aromaticity.

Main Methods:

  • Utilizing crystallographic data of existing compounds.
  • Performing ab initio calculations to determine Nuclear-Independent Chemical Shift (NICS(0)) values.
  • Analyzing the relationship between spiro-atom identity and aromaticity.

Main Results:

  • The study proposes that these systems exhibit Möbius 4n pi-electron aromaticity in each ring.
  • NICS(0) values indicate varying degrees of Möbius aromaticity.
  • Möbius aromaticity was found to increase as the spiro-atom changes from Al to P, and from P to As.

Conclusions:

  • Bis and tris-spiro 7-membered ring systems can be classified as spiroaromatic.
  • The electronic properties and Möbius aromaticity are tunable by altering the central spiro-atom.
  • This work provides a new perspective on the aromaticity of complex spirocyclic compounds.

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