Synthesis and thermal stability of a novel polyfunctional pyridine-based derivative featuring amino, nitro, and guanidine groups

Abstract

A new pyridine derivative 1-(4-amino-3,5-dinitropyridin-2-yl) guanidine (ADG) was synthesized through nitration and substitution reaction using 4-amino-2-cholopyridine as raw material. Its structure was characterized by spectroscopy, nuclear magnetic resonance, and mass spectrometry. The crystal of ADG is monoclinic, space group Pbca with crystal parameters of a = 7.23 Å, b = 14.56 Å, c = 17.93 Å, α = β= γ= 90 Å, V = 1911 Å3, μ = 0.143 mm−1, and Z = 8. This new molecule exhibits moderate density ( ρ= 1.677 g cm−3), good thermal stability with a decomposition temperature of 217 °C, and moderate detonation property with detonation pressure of 20.83 GPa and detonation velocity of 7.00 km s−1. The Hirshfeld surface analysis revealed a significant contribution of weak interactions to the packing forces for molecules. Electron localization function analysis indicates that there is substantial electron localization in regions of C–H, N–H, and N–O covalent bond sites.

Synthesis of Heat-Resistant and Low-Sensitivity Energetic Materials Based on Hydrazine Bridge Linkage

“…The synthetic route of 2,2′-hydrazo-bis­(2-amino-3,5-dinitropyridine) ( 2 ) and 2,2′-hydrazo-bis­(4-amino-3,5-dinitropyridine) ( 4 ) is shown in Scheme . The vicinal amino–nitro groups precursors, 6-chloro-2-amino-3,5-dinitropyridine ( 1 ) and 2-chloro-4-amino-3,5-dinitropyridine ( 3 ), were synthesized according to the reported methods. , Compound 1 was reacted with hydrazine hydrate in a molar ratio of 1:1 to obtain 2-amino-6-hydrazineyl-3,5-dinitropyridine with a hydrazine group replaced from the chlorine atom, which has been previously reported . Interestingly, when the molar ratio of compound 1 and hydrazine hydrate was adjusted to 2:1, the hydrazine-bridged compound 2 with high detonation performance and high thermal stability was successfully obtained.…”