Enhancing energetic properties and sensitivity by incorporating amino and nitramino groups into a 1,2,4-oxadiazole building block

Yongxing Tang, Haixiang Gao, Lauren A. Mitchell, Damon A. Parrish, Jean'Ne M. Shreeve

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

Abstract

A single nitrogen-rich heterocyclic ring with many energetic groups is expected to exhibit excellent detonation performance. We report an effective approach for the synthesis of 3-amino-5-nitramino-1,2,4-oxadiazole, which has nitramino and amino groups in the same building block. The single-crystal X-ray structure shows layered hydrogen-bonding pairs as well as the presence of a water molecule which ensure insensitivity. Through incorporation of a cation, the hydrazinium or hydroxylammonium salts exhibit good energetic performance and acceptable sensitivities. Going with a bang: Hydrazinium 1,2,4-oxadiazolate combines amino and nitramino groups in a single heterocyclic ring and can be synthesized in a straightforward manner from inexpensive starting materials. Owing to its high performance and insensitivity, this compound may find practical use as an RDX replacement.

Original languageEnglish (US)
Pages (from-to)1147-1150
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number3
DOIs
StatePublished - Jan 18 2016

Keywords

  • amines
  • detonation
  • energetic materials
  • nitramino groups
  • oxadiazoles

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