TY - JOUR
T1 - A comparative study of the structure, energetic performance and stability of nitro-NNO-azoxy substituted explosives
AU - Wang, Yuan
AU - Li, Shenghua
AU - Li, Yuchuan
AU - Zhang, Rubo
AU - Wang, Dong
AU - Pang, Siping
N1 - Publisher Copyright:
© The Royal Society of Chemistry 2014.
PY - 2014/12/28
Y1 - 2014/12/28
N2 - 2,4-Dinitro-NNO-azoxytoluene and 2,6-dinitro-4-nitro-NNO-azoxytoluene were synthesized as energetic compounds. Their structures and properties were studied by X-ray diffractometry, nuclear magnetic resonance and infrared spectroscopy. The differences between the nitro-NNO-azoxy and nitro groups are discussed. The detonation properties, as predicted using EXPLO5, indicate that the detonation velocity and pressure of 2,4-dinitro-NNO-azoxytoluene were greater by 21.7% and 74.3%, respectively, than those of 2,4-dinitrotoluene. Nucleus independent chemical shift analysis was used to investigate skeleton aromaticity and the effect of the nitro-NNO-azoxy and nitro groups on ring aromaticity. Electrostatic potential, bond dissociation energy, Mulliken charges and Wiberg bond order were estimated by density functional theory to establish the molecular electron distribution and stabilities of the compounds. The nitro-NNO-azoxy group has a stronger electron-withdrawing property than that of the nitro group.
AB - 2,4-Dinitro-NNO-azoxytoluene and 2,6-dinitro-4-nitro-NNO-azoxytoluene were synthesized as energetic compounds. Their structures and properties were studied by X-ray diffractometry, nuclear magnetic resonance and infrared spectroscopy. The differences between the nitro-NNO-azoxy and nitro groups are discussed. The detonation properties, as predicted using EXPLO5, indicate that the detonation velocity and pressure of 2,4-dinitro-NNO-azoxytoluene were greater by 21.7% and 74.3%, respectively, than those of 2,4-dinitrotoluene. Nucleus independent chemical shift analysis was used to investigate skeleton aromaticity and the effect of the nitro-NNO-azoxy and nitro groups on ring aromaticity. Electrostatic potential, bond dissociation energy, Mulliken charges and Wiberg bond order were estimated by density functional theory to establish the molecular electron distribution and stabilities of the compounds. The nitro-NNO-azoxy group has a stronger electron-withdrawing property than that of the nitro group.
UR - http://www.scopus.com/inward/record.url?scp=84911908378&partnerID=8YFLogxK
U2 - 10.1039/c4ta04716h
DO - 10.1039/c4ta04716h
M3 - Article
AN - SCOPUS:84911908378
SN - 2050-7488
VL - 2
SP - 20806
EP - 20813
JO - Journal of Materials Chemistry A
JF - Journal of Materials Chemistry A
IS - 48
ER -
