Straightforward Synthesis of Insensitive 2-(1-Hydroxy-2,2-dinitrovinyl)guanidine and Its Guanidinium Dinitromethanide Salt as a High Energy Density Material

Abstract

High energetic 2-(1-hydroxy-2,2-dinitrovinyl)­guanidine and guanidinium dinitromethanide (GDNM) salt were synthesized in one and two steps using a simple and cost-effective methodology from commercially available inexpensive starting materials with a high yield. NMR, IR spectroscopy, elemental analysis, and differential scanning calorimetry studies were used to characterize compound 2a and GDNM salt. Single-crystal XRD, Hirshfeld surface analysis, and SEM analysis were used to study the crystal structure, hydrogen-bonding/noncovalent interactions, and morphology of the GDNM salt, respectively. The physicochemical and energetic properties of compound 2a and GDNM salt reveal their good energetic performance, specific impulse, and high mechanical insensitivity, which are better than that of propellants such as ADN and AP and close to that of the benchmark explosives such as RDX and FOX-7.

Elevating the energetic capabilities of metal coordination compounds by incorporating nitrate anions

“…Balancing the inherent contradiction between the energy and sensitivity of EMs has emerged as a significant focus in research within the field. 4–7…”

Symmetric Refunctionalization of Diaminodinitropyrazine with Hydrazine and Aminotetrazole: Strategy for Enhancing Detonation Performance and Safety in Energetic Materials

“…The development of new energetic materials (EMs) with high energy, good thermal stability, lower mechanical sensitivities, and ease of synthesis for future aerospace civilian and military applications is a perennially pursued goal. − Worldwide research on energetic materials employs diverse strategies for enhancing the energy content of these materials, striving to strike a balance between targeted performance attributes and chemical/mechanical stability. This is a challenging task as these attributes often exhibit conflicting tendencies; for instance, a higher energy content can lead to a lower thermal stability and increased sensitivity to external stimuli. − A particularly promising avenue in advancing EMs involves the meticulous design of synthesis pathways for heterocyclic frameworks with an increased nitrogen content and varied explosophoric groups.…”

Exploring the Explosive Potential: Synthesis and Characterization of Ring-Fused Oxadiazolo[3,4-b]pyrazine 1-Oxide Polymorphs with Balanced Energetic Properties

“…Energetic compounds rich in nitrogen and oxygen contents are emerging as promising alternatives to traditional explosives, offering a greener solution by addressing environmental concerns while delivering high energy output per unit mass. Typically, initiating these materials involves the rupture of covalent bonds such as C–N, N–O, or N–N, leading to a quick energy release and eventual detonation. − Consequently, designing materials centered around nitrogen-rich heterocycles has proven to be a practical approach for developing new energetic materials. In recent years, many new, insensitive, yet powerful energetic materials have been introduced, all of which are based on nitrogen-rich heterocycles. − More importantly the pyrazine, tetrazole, and furoxan backbone have garnered significant attention as the central structure for both primary and secondary explosives due to their favorable characteristics, including high heats of formation and ease of synthesis. − Moreover, while numerous N-oxide substituted mono and C–C bonded azole-based energetic heterocyclic compounds have been reported, there are comparatively few reports concerning those with fused ring backbones. − The introduction of the N-oxide in heterocyclic framework is known to enhance the oxygen balance and crystal packing due to its zwitterionic structure and large dipole moment, which helps to achieve better density and detonation properties.…”