ChemInform Abstract: Synthesis of (.+‐.)‐trans‐1,2,3‐Tri(nitroamino)cyclopropane.

Ivshin, V. P.; Komelin, M. S.; Тартаковский, В. А.

doi:10.1002/chin.199952086

Cited by 3 publications

(3 citation statements)

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“…Baum and coworkers [88] reported the synthesis of 1,1,3,3-tetranitro cyclobutane (TNCB) (XX), by the nitration of 1,3-dinitrocyclobutane with AgNO 3 and NaNO 2 . Recently, Tartakovskii and coworkers [89] reported the synthesis of trans-1,2,3-tris(nitramino)cyclopropane (NACP) (XXI) using cyclopropyl triamine and Ac 2 O/HNO 3 or trifluroacetic acid/HNO 3 .…”

Section: 33-trinitroazetidine (Tnaz)mentioning

confidence: 99%

Advances in science and technology of modern energetic materials: An overview

Badgujar

Talawar

Asthana

et al. 2008

Journal of Hazardous Materials

896

487

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Section: 33-trinitroazetidine (Tnaz)mentioning

confidence: 99%

Advances in science and technology of modern energetic materials: An overview

Badgujar

Talawar

Asthana

et al. 2008

Journal of Hazardous Materials

896

487

View full text Add to dashboard Cite

“…However, TNAZ has a high volatility [3] which seriously affects its application. Many other small-ring compounds, such as 3-nitro-1,2,4-triazole-5-one with a five-membered ring [15], 1,1,3,3-tetranitro cyclobutane with a four-membered ring [16] and trans-1,2,3-tris(nitramino)cyclopropane with a three-membered ring [17] have also been reported. Although various energetic compounds with small rings have been found, their OBs are generally negative, which is not beneficial for them as energetic oxidizers.…”

Section: Introductionmentioning

confidence: 99%

Theoretical studies on the stability, detonation performance and possibility of synthesis of the nitro derivatives of epoxyethane

Zhang

Gong

2014

J Mol Model

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Compounds with heterocyclic rings and NO2 groups have drawn much attention as high energy density compounds in recent years. In this study, the nitro derivatives 1-4 of epoxyethane (ETO) were investigated, and their synthetic possibilities in thermodynamics and thermal stability were predicted. The trigger bond for 1, 2 and 3 is the C-C bond, but for 4 it is the C-NO2 bond. The bond dissociation energies (EBDs) were estimated to be 205.40-164.86 kJ mol(-1) and h 50s were 53-126 cm. EBD, h 50 and energy gap all decrease from 1 to 4. A linear relationship exists between the strain energy and the number of the NO2 group. Derivative 2 has a zero oxygen balance and possesses the best detonation properties (D=8.77 km s(-1) and P=33.88 GPa) as a single explosive. Derivatives 3 and 4 used as oxidizers in the composite explosives of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) produce very good detonation performance (D=9.36 km s(-1), P=40.15 GPa and I s = 281.56 s for 3/RDX, and D=9.45 km s(-1), P=41.04 GPa and I s=280.34 s for 4/RDX). The intermolecular hydrogen bonding and dispersion interactions of 3/RDX and 4/RDX show that the compatibilities of these composites are acceptable.

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“…Baum and coworkers reported the synthesis of 1,1,3,3‐tetranitrocyclobutane Tartakovskii et al . studied the synthesis of trans‐1,2,3‐tris(nitramino)cyclopropane . OBs of these compounds are also negative.…”

Section: Introductionmentioning

confidence: 99%

A theoretical study on the stability and detonation performance of 2,2,3,3‐tetranitroaziridine (TNAD)

Zhang

Yang

Wang

et al. 2014

J of Physical Organic Chem

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In recent years, there has been a considerable interest in developing high oxygen compounds as oxidizers for, for example, composite explosives. 2,2,3,3-Tetranitroaziridine (TNAD) is a new designed compound with high oxygen balance (25.11%) and is environmentally friendly. A synthesis route of TNAD was suggested in this study, and the thermodynamic possibilities of reactions were evaluated by the changes in the free energy obtained with the density functional theory (DFT). The strong strain energy (E s = 292.28 kJ/mol) of TNAD leads the C-C bond in the ring more fragile than the C-NO 2 bond, and the activation energy (E a ) of pyrolysis of the C-C bond (119.14 kJ/mol at the B3LYP/6-31G* level of DFT) is higher than that of 2,4,6trinitrotoluene (TNT) (113.00 kJ/mol). The topological analysis with the contour maps of electron density was used to show the changes of the electron density at the critical points (BCP) in the process of homolysis of the C-C bond. In addition, the energy gap between the frontier orbitals of TNAD (ΔE g = 5.22 eV) is slightly higher than that of 1,3,3-trinitroazetidine (TNAZ, 5.06 eV). And the HOMO → LUMO transition plays important roles in the UV spectrum. The noncovalent interactions in the TNAD/RDX composite were estimated to be stronger than that in TNAZ/RDX, that is, the former may have better compatibility than the latter. TNAD/RDX with the weight ratio of w TNAD /w RDX = 0.46/0.54 has the wonderful performance (D = 9.14 km/s, P = 37.30 GPa, and I s = 285.47 s) which is better than that (D = 8.85 km/s, P = 35.09 GPa, and I s = 272.33 s) of TNAZ/RDX with the same weight ratio.

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ChemInform Abstract: Synthesis of (.+‐.)‐trans‐1,2,3‐Tri(nitroamino)cyclopropane.

Abstract: Synthesis of (±)-trans-1,2,3-Tri(nitroamino)cyclopropane.--(IVSHIN, V. P.; KOMELIN, M. S.; TARTAKOVSKII, V. A.; Russ.

Cited by 3 publications

References 0 publications

Advances in science and technology of modern energetic materials: An overview

Advances in science and technology of modern energetic materials: An overview

Theoretical studies on the stability, detonation performance and possibility of synthesis of the nitro derivatives of epoxyethane

A theoretical study on the stability and detonation performance of 2,2,3,3‐tetranitroaziridine (TNAD)

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