14,16,34,36,54,56,74,76-Octanitro-2,4,6,8-tetraoxa-1,3,5,7(1,3)-tetrabenzenacyclooctaphane and its derivatives: thermally stable explosives with outstanding properties

Abstract

Herein, the novel, thermally stable explosive 1⁴,1⁶,3⁴,3⁶,5⁴,5⁶,7⁴,7⁶-octanitro-2,4,6,8-tetraoxa-1,3,5,7(1,3)-tetrabenzenacyclooctaphane (4a) and its derivatives are reported. These compounds can be prepared via a facile synthetic procedure and show outstanding properties (detonation velocity, detonation pressure, sensitivity towards mechanical stimuli, and temperature of decomposition). Moreover, 4a and its derivatives were isolated and characterized via mass spectrometry and multinuclear (¹H, ¹³C) NMR spectroscopy. The structures of 4a and 4b in the crystalline state were determined via low-temperature single-crystal X-ray diffraction. From the calculated standard molar enthalpies of formation (CBS-4M) and densities, the Chapman–Jouguet detonation properties were predicted using the EXPLO5 V6.01 thermochemical computer code. The sensitivities of 4a and its derivatives towards impact, friction, and electrostatic discharge were determined.