Theoretical Studies on Triacetonetriperoxide (Tatp) Derivatives to Improve Their Performance

Miao, Zongcheng; Li, Faan; Luan, Yi

doi:10.21577/0100-4042.20170295

Cited by 2 publications

(7 citation statements)

References 30 publications

(36 reference statements)

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“…The densities of DADP3F, DADPNH 2 and DADPNO 2 are 1.90, 1.35 and 1.59 g cm −3 at the B3LYP level respectively. These values are approximately equal to their TATP congeners 11 (shown in Table 5), because they all have the same carbon, hydrogen, oxygen, nitrogen and fluorine content. DADP3F and TATP3F both have higher density than others because of the fluorine atom and trifluoromethyl, which The molecular weight.…”

Section: Detonation Performancementioning

confidence: 87%

“…Figure 6 shows that the LUMOs were mainly located in the substituted groups, which is consistent with other multi-peroxidic compounds. 11 The HOMOs were almost distributed evenly throughout the atoms. The intramolecular charges transfer from the electron donor to the electron acceptor, substituted groups.…”

Section: Electronic Structurementioning

confidence: 99%

“…Since the electron-withdrawing -NO 2 groups can decrease electron cloud densities of O-O bonds and then reduce the distance, the bond lengths in DADPNO 2 were all lower than the minimum of the bond lengths in the TATP derivatives. 11 Tables 4S-7S summarize the detailed information on the standard orientation of each atom.…”

Section: Geometrical Structuresmentioning

confidence: 99%

“…It can be seen that heats of formation of DADP and its derivatives are all higher than those of TATP counterpart. 11 Nitro, amino and trifluoromethyl are important group in energetic materials. Nitro and amino group can improve density and heat of formation, while trifluoromethyl will reduce heat of formation but increase density dramatically.…”

Section: Detonation Performancementioning

confidence: 99%

“…[1][2][3] Traditional energetic materials include 2,4,6-trinitrotoluene (TNT), 4 1,3,5-trinitro-1,3,5-triazacyclohexane (RDX), 5 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane (HMX), 6 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20), 7 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) 8 and other poly-nitrogen oxygen-rich compounds. 9,10 TATP (triacetonetriperoxide) and its derivatives have been reported to be novel energetic materials, 11 while DADP (diacetonediperoxide), whose structure is shown in Figure 1, is another promising energetic material in the multi-peroxidic compound family. 12,13 TATP has been extensively used by terrorists in terrorist attacks because of its low cost and simple production process.…”

Section: Introductionmentioning

confidence: 99%

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Theoretical Studies on Diacetonediperoxide Derivatives and Comparisons With Other Multi-Peroxidic Compounds

Miao¹,

Li²,

Fan³

et al. 2020

Quim. Nova

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Recebido em 22/03/2020; aceito em 31/03/2020; publicado na web em 20/05/2020 Diacetonediperoxide (DADP) derivatives were investigated with density functional theory (DFT) methods at the DFT-B3LYP and M06-2X/6-311++G (d, p) levels and were also compared with other multi-peroxidic compounds. The investigated derivatives were 3,6-dimethyl-3,6-diamine-1,2,4,5-tetraoxane (DADPNH 2 ), 3,6-dimethyl-3,6-dinitro-1,2,4,5-tetraoxane (DADPNO 2 ), and 3,6-dimethyl-3,6-bis(trifluoromethyl)-1,2,4,5-tetraoxane (DADP3F). The investigations were focused on detonation performance and stability which were determined according to geometrical and electronic structure. The results of the simulation revealed that DADP derivatives are less sensitive than some other organic peroxidic compounds. In addition, detonation performance, including explosion heat (Q), detonation velocity (D), and detonation pressure (P), was estimated according to density and heat of formation using EXPLO 5 software. The results revealed that DADPNO 2 has better detonation performance (Q = 5543 kJ kg -1 , P = 23.7 GPa, D = 7631 m s -1 ) compared with traditional explosive 2,4,6-trinitrotoluene (TNT; Q = 5418 kJ kg -1 , P = 19.0 GPa, D = 6950 m s -1 ). Therefore, it is a novel candidate for use as an energetic material.

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Section: Detonation Performancementioning

confidence: 87%

Section: Electronic Structurementioning

confidence: 99%

Section: Geometrical Structuresmentioning

confidence: 99%

Section: Detonation Performancementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Theoretical Studies on Diacetonediperoxide Derivatives and Comparisons With Other Multi-Peroxidic Compounds

Miao¹,

Li²,

Fan³

et al. 2020

Quim. Nova

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Chiral explosives: A theoretical investigation of structure and chiroptical properties of triacetone triperoxide and hexamethylene triperoxide diamine

Puente

Polavarapu

2023

Chirality

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Triacetone triperoxide (TATP) and hexamethylene triperoxide diamine (HMTD) are cyclic peroxides that exhibit atropisomerism resulting from restricted rotation around three peroxide bonds. As a result, one pair of enantiomers with D 3 symmetry and another pair of enantiomers with C 2 symmetry can be identified. Previous studies, based on mass spectrometry data and computational results, have shown that conformations of TATP with D 3 and C 2 symmetry can be isolated. Assuming that enantiomer samples of TATP and HMTD can be obtained with sufficient enantiopurity, we investigated their chiroptical properties, namely, optical rotatory dispersion (ORD), vibrational circular dichroism (VCD), and Raman optical activity (VROA). ORD curves and VCD spectra are seen to be very similar for D 3 -and C 2 -symmetric atropisomers with the same overall helicity. Predicted VROA results, however, show significant differences between D 3 -and C 2 -symmetric atropisomers with the same overall helicity. The D 3 -symmetric atropisomer is predicted to exhibit considerably larger magnitude vibrational optical activity signals than the C 2symmetric atropisomer.explosives, hexamethylene triperoxide diamine, optical rotatory dispersion, Raman optical activity, transition states, triacetone triperoxide, vibrational circular dichroism [This article is part of the Special issue: Chiral Materials. See the first articles for this special issue previously published in Volumes 34:12, 35:2 and 35:3. More special articles will be found in this issue as well as in those to come.]

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Theoretical Studies on Triacetonetriperoxide (Tatp) Derivatives to Improve Their Performance

Cited by 2 publications

References 30 publications

Theoretical Studies on Diacetonediperoxide Derivatives and Comparisons With Other Multi-Peroxidic Compounds

Theoretical Studies on Diacetonediperoxide Derivatives and Comparisons With Other Multi-Peroxidic Compounds

Chiral explosives: A theoretical investigation of structure and chiroptical properties of triacetone triperoxide and hexamethylene triperoxide diamine

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