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Pentazoles are the final member in the azole series of compounds and comprise and cyclo-N5 ring with one hydrogen attached. Aryl substituted pentazoles have been successfully synthesized for many years, but more recently have served as the starting point for the synthesis of pentazolate (cyclo-N5−) salts. These salts possess dual aromaticity and are stabilized in the solid state by intermolecular interactions such as coordination and hydrogen bonds, π-π and van der Waals interactions. Synthetic advances have enabled the routine isolation of numerous pentazolate salts, either directly or through metathesis reactions, facilitating thorough spectroscopic characterization as well as their examination as novel energetic materials.
Original languageEnglish
Title of host publicationComprehensive Heterocyclic Chemistry IV
Subtitle of host publicationa review of the literature 2008-2021
EditorsDavid Black, Janine Cossy, Christian Stevens
Place of PublicationOnline
Number of pages14
ISBN (Electronic)9780128186565
ISBN (Print)9780128186558
Publication statusPublished - 2022


  • Pentazoles
  • Azole
  • Compounds
  • Hydrogen bonding
  • Oxidative cleavage
  • Cyclo-N
  • η -σ bonds
  • Dual aromaticity
  • Metathesis reactions
  • Energetic materials
  • Pentazolate salts
  • π-π stacking
  • Pentazole


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