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Molecules 2012, 17(5), 5040-5049; doi:10.3390/molecules17055040

Synthesis and Characterization of 5-Nitro-2-nitratomethyl-1,2,3,4-tetrazole: A High Nitrogen Energetic Compound with Good Oxygen Balance

1
School of Material Science & Engineering, State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, China
2
School of Life Science, Beijing Institute of Technology, Beijing 100081, China
*
Author to whom correspondence should be addressed.
Received: 29 February 2012 / Revised: 18 April 2012 / Accepted: 20 April 2012 / Published: 3 May 2012
(This article belongs to the Section Organic Synthesis)
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Abstract

The synthesis of 5-nitro-2-nitratomethyl-1,2,3,4-tetrazole (4) and its full characterization are given here. Compound 4 was synthesized through the nitration of 5-nitro-2-hydroxymethyl-tetrazole (3) with fuming nitric acid and acetic anhydride and its structure was characterized by MS, FT-IR, 1H-NMR and 13C-NMR techniques. The crystal structure of 4 was determined by X-ray single crystal diffraction analysis. The compound belongs to the orthorhombic system with space group Pna2(1), and its crystal parameters were a = 2.121(8) nm, b = 0.5281(19) nm, c = 0.6246(2) nm, Z = 4, V = 0.6995(4) nm3, Dc = 1.805 g/cm3, F(000) = 384, μ = 0.174 mm−1. A theoretical study of 4 has been performed, using quantum computational density functional theory (B3LYP methods) with 6-31G* basis sets as implemented in the Gaussian 03 program suite. The obtained heat of formation (HOF) for 4 was 228.07 kJ·mol−1, the detonation pressure (P) values calculated for 4 was 37.92 GPa, the detonation velocity (D) can reach 9260 m·s−1, and the oxygen balance was zero (Q), making 4 a competitive energetic compound.
Keywords: synthesis; characterization; 5-nitro-2-nitratomethyl-1,2,3,4-tetrazole; crystal structure; quantum calculation; high nitrogen energetic compound; oxygen balance synthesis; characterization; 5-nitro-2-nitratomethyl-1,2,3,4-tetrazole; crystal structure; quantum calculation; high nitrogen energetic compound; oxygen balance
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Li, Y.; Liu, W.; Pang, S. Synthesis and Characterization of 5-Nitro-2-nitratomethyl-1,2,3,4-tetrazole: A High Nitrogen Energetic Compound with Good Oxygen Balance. Molecules 2012, 17, 5040-5049.

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