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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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Organohypervalent heterocycles.

Ravi Kumar1, Toshifumi Dohi2, Viktor V Zhdankin3

  • 1Department of Chemistry, J C Bose University of Science and Technology, YMCA, NH-2, Sector-6, Mathura Road, Faridabad, 121006, Haryana, India. ravi.dhamija@rediffmail.com.

Chemical Society Reviews
|March 28, 2024
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Summary
This summary is machine-generated.

This review explores hypervalent heterocyclic molecules, focusing on their structure, synthesis, and enhanced thermal stability. These compounds, featuring main-group elements with expanded valence shells, offer unique chemical properties.

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Area of Science:

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Hypervalent molecules contain main-group elements with more than eight valence electrons.
  • Hypervalent heterocycles exhibit enhanced thermal stability compared to acyclic analogs.
  • The definition of hypervalency is debated, particularly for elements involved in double bonds.

Purpose of the Study:

  • To review the structural and synthetic chemistry of hypervalent heterocyclic compounds.
  • To highlight the unique properties conferred by hypervalency in cyclic systems.
  • To cover hypervalent derivatives of nonmetal main-group elements.

Main Methods:

  • Literature review of structural and synthetic studies.
  • Analysis of chemical properties, focusing on thermal stability.
  • Classification of hypervalent compounds based on electronic structure.

Main Results:

  • Hypervalent heterocycles, especially those with bromine and iodine, show increased thermal stability.
  • Elements reviewed include boron, silicon, nitrogen, carbon, phosphorus, sulfur, selenium, bromine, and iodine (III and V).
  • Compounds with zwitterionic double bonds are not classified as hypervalent.

Conclusions:

  • Hypervalent heterocycles represent a unique class of compounds with distinct structural and synthetic characteristics.
  • Their enhanced stability and diverse elemental composition offer potential for novel applications.
  • Further research into the fundamental chemistry of hypervalency in cyclic systems is warranted.