Synthesis of Nitro Derivatives of Triazoles

Yu-xiang, OU; Boren, Chen; Li, Jiarong; Dong, Shuying; Li, Jianjun; Jia, Haiying

doi:10.3987/rev-93-sr21

Cited by 35 publications

(19 citation statements)

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“…For compound (9), when the position of nitro group on 1,2,3-triazole ring moves from 4-position to 5-position, the BDE of the initial scission bond of the obtained compound (i.e., compound 10) decreases drastically and equals to 33.3 kcal/mol. When the position of nitro group on 1,2,3-triazole ring moves from 4-position to 5-position for compound (5), the BDE of the initial scission bond of the obtained compound is nearly the same as the BDE of the initial scission bond of compound (5).…”

Section: Resultsmentioning

confidence: 85%

“…It is noted that the C 1 -N 1 BDE is the biggest for compound (5) and equal to 68.2 kcal/mol, which is much bigger than those of the C 3 -N 3 and C 4 -N 4 bonds, the C 4 -N 4 BDE is the smallest. For compound (6), the BDEs of the C 3 -N 3 and Table 1 Bond dissociation energies (BDE, kcal/mol) for seven title compounds at B3LYP/6-31G* and B3P86/6-31G* levels Compound B3LYP/6-31G* B3P86/6-31G* H 50 Numbers in bold mean that the corresponding bond is most reactive in the studied compound C 5 -N 5 bonds are equivalent, and their BDEs are all equal to 63.9 kcal/mol.…”

Section: Resultsmentioning

confidence: 96%

“…1, we can notice that compounds (5), (6), (9), (10), and (11) are isomeric compounds. When the position of nitro group on benzene ring moves from 3-position to 2-position for compound (5), the BDE of the initial scission bond increases from 56.1 to 58.3 kcal/mol. For compound (9), when the position of nitro group on 1,2,3-triazole ring moves from 4-position to 5-position, the BDE of the initial scission bond of the obtained compound (i.e., compound 10) decreases drastically and equals to 33.3 kcal/mol.…”

Section: Resultsmentioning

confidence: 97%

“…For the isodesmic reaction (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13), heat of reaction DH 298 at 298 K can be calculated from the following equation:…”

Section: Theory and Computational Detailsmentioning

confidence: 99%

“…The nitrotriazole derivatives are of interesting energetic compounds [4]. The syntheses of nitrotriazole derivatives as energetic materials and as intermediates to energetic materials have received a great deal of attention in the past 10 years [5]. Baryshnikov et al [6] have synthesized several 4-nitro-1,2,3-triazoles by reacting sodium azide with a variety of 1,1-dinitroethylene synthons.…”

Section: Introductionmentioning

confidence: 99%

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Theoretical studies on a series of 1,2,3-triazoles derivatives as potential high energy density compounds

Zhang

2011

Struct Chem

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Based on the full-optimized molecular geometric structures at B3LYP/6-31G* and B3P86/6-31G* levels, the densities (q), detonation velocities (D), and pressures (P) for a series of 1,2,3-triazole derivatives, as well as their thermal stabilities, were investigated to look for high energy density compounds (HEDCs). The heats of formation (HOFs) are also calculated via designed isodesmic reactions. The calculations on the bond dissociation energies (BDEs) indicate that the BDEs of the initial scission step are between 53 and 70 kcal/mol, and 4-nitro-1,2,3-triazole is the most reactive compound, while 1-(2 0 ,4 0 -dinitrophenyl)-5-nitro-1,2,3-triazole is the least reactive compound for 1,2,3-triazole derivatives studied. The condensed phase heats of formation are also calculated for the title compounds. These results would provide basic information for the further studies of HEDCs. The detonation data of 1-(3 0 ,4 0 -dinitrophenyl)-4-nitro-1,2,3-triazole and 1-(2 0 ,4 0 -dinitrophenyl)-4-nitro-1,2,3-triazole show that they meet the requirement for HEDCs.

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Section: Resultsmentioning

confidence: 85%

Section: Resultsmentioning

confidence: 96%