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Download fileA Study of Dinitro-bis-1,2,4-triazole-1,1′-diol and Derivatives: Design of High-Performance Insensitive Energetic Materials by the Introduction of N‑Oxides
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posted on 2013-07-03, 00:00 authored by Alexander
A. Dippold, Thomas M. KlapötkeIn
this contribution we report on the synthesis and full structural
as well as spectroscopic characterization of 3,3′-dinitro-5,5′-bis-1,2,4-triazole-1,1′-diol
and nitrogen-rich salts thereof. The first synthesis and characterization
of an energetic 1-hydroxy-bistriazole in excellent yields and high
purity is presented. This simple and straightforward method of N-oxide
introduction in triazole compounds using commercially available oxone
improves the energetic properties and reveals a straightforward synthetic
pathway toward novel energetic 1,2,4-triazole derivatives. X-ray crystallographic
measurements were performed and deliver insight into structural characteristics
and strong intermolecular interactions. The standard enthalpies of
formation were calculated for all compounds at the CBS-4 M level of
theory, revealing highly positive heats of formation for all compounds.
The energetic properties of all compounds (detonation velocity, pressure,
etc.) were calculated using the EXPLO5.05 program, and the ionic derivatives
show superior performance in comparison to the corresponding compounds
bearing no N-oxide. All substances were characterized in terms of
sensitivities (impact, friction, electrostatic) and thermal stabilities,
and the ionic derivatives were found to be high thermally stable,
insensitive compounds that are exceedingly powerful but safe to handle
and prepare.