Theoretical Study on Nitroimine Derivatives of Azetidine as High-Energy-Density Compounds

Abstract

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Mechanical Properties and Temperature and Pressure Effects on the Crystal Structure of (2S,3S,4R)-2,3,4-(Trinitratomethyl)-1-nitroazetidine (TMNA) by Single-Crystal X-ray Diffractometry and Density Functional Theory

“…Moiety modification and moiety integration exemplify two approaches for synthesizing energetic azetidines. The former approach involves adding explosophores to the azetidine moiety, whereas the latter involves the union between a modified energetic azetidine moiety and an existing energetic chemical system. − ,− Energetic 3,3-dinitroazetidine (DNAZ), 3-nitrato-1-nitroazeditine (NNA), 1,3,3-trinitroazetidine (TNAZ), and nitroimine azetidine (NIA) illustrate examples of moiety modification (Figure ). The crystal structure of DNAZ presents two nitro groups attached to the azetidine ring carbon atom, whereas NNA presents a nitro group attached to the azetidine ring nitrogen atom and a nitrato group (−O–NO 2 ) attached to the carbon atom opposite the nitrogen atom. , In contrast, the crystal structure of TNAZ reveals a nitro group attached to the azetidine nitrogen atom in addition to a pair of nearly perpendicular nitro groups (–NO 2 ) attached to the carbon atom opposite the nitro amino ring atom.…”

“…More recently, Li and Li performed a computation study of NIA derivatives generated by bonding one or more nitroimine functional groups (�N−NO 2 ) to the azetidine ring atoms. 33 They claim that the C−N bond strength in the four-membered ring determines their stability, whereas N−NO 2 homolysis triggers their decomposition. The respective density, detonation velocity (V det ), and detonation pressure (P det ) of the various molecules range between 1.51 and 1.81 g/cm 3 , between 7230 and 9060 m/s, and between 20.7 and 36.5 GPa, with the structure containing the nitroimine group on each azetidine ring atom presenting the highest density and detonation velocity.…”

“…However, safety and processing concerns have limited its use as a melt-castable replacement for energetic trinitrotoluene (TNT). More recently, Li and Li performed a computation study of NIA derivatives generated by bonding one or more nitroimine functional groups (N–NO 2 ) to the azetidine ring atoms . They claim that the C–N bond strength in the four-membered ring determines their stability, whereas N–NO 2 homolysis triggers their decomposition.…”

CAS Calculation of the Excited States of the Methylthio Neutral Radical and Its Ions

“…The methylthio neutral radical (CH 3 S) is an important sulfur-containing compound in atmospheric chemistry. − These species are mainly from the detachment reactions of CH 3 SSCH 3 , which is sent from the combustion reactions in the industry and the animal decay in the ocean . Under the sunlight radiation condition, these organosulfur compounds participate in a series of photochemical reactions, and, although a minor constituent, may play a key role in the atmospheric sulfur cycle and contribute to the acid precipitation problem.…”