Nitroimino-tetrazolates and oxy-nitroimino-tetrazolates.

Highly energetic 1,1'-ethylenebis(oxy)bis(5-nitroimino-tetrazolate) salts were obtained by reacting equimolar quantities of the acidic 1,1'-ethylenebis(oxy)bis(5-nitroimino-tetrazole) and energetic bases in aqueous solution. Additionally, metathesis of silver 1,1'-ethylenebis(oxy)bis(5-nitroimino-tetrazolate) with diaminoguanidinium chloride or triaminoguanidinium chloride gave the corresponding oxy-nitroimino-tetrazolate salt. These salts were fully characterized using IR and multinuclear NMR spectroscopy, elemental analysis, and differential scanning calorimetry (DSC), and, in some cases, 2·2H(2)O, 8·2H(2)O, 10, 13·2H(2)O and 14, with single crystal X-ray structuring. The heats of formation for all compounds were calculated with Gaussian 03 and then combined with measured densities to determine detonation pressures (P) and velocities (D) of the energetic materials (Cheetah 5.0). The impact sensitivities of all salts were found to be less than those of the parent compounds. The physical and detonation properties of these oxy-nitroimino-tetrazolate salts are comparable to the analogous newly prepared diaminoguanidinium and triaminoguanidinium 1,1'-ethylenebis(5-nitroimino-tetrazolate)s.

[1]  J. Shreeve,et al.  High-density energetic mono- or bis(oxy)-5-nitroiminotetrazoles. , 2010, Angewandte Chemie.

[2]  B. Twamley,et al.  Carbonyl and oxalyl bridged bis(1,5-diaminotetrazole)-based energetic salts. , 2009, Chemistry.

[3]  T. Klapötke,et al.  Crystal Structures of Mono-, Di-, and Triaminoguanidinium Sulfate, as Well as Azidoformamidinium Sulfate: Important Precursors for Syntheses of Nitrogen Rich Ionic Compounds , 2009 .

[4]  J. Shreeve,et al.  1,3-Diazido-2-(azidomethyl)-2-propylammonium salts. , 2009, Inorganic chemistry.

[5]  T. Klapötke,et al.  New energetic materials: Synthesis and characterization of copper 5-nitriminotetrazolates , 2009 .

[6]  J. Shreeve,et al.  Energetic ethylene- and propylene-bridged bis(nitroiminotetrazolate) salts. , 2009, Chemistry.

[7]  J. Shreeve,et al.  Energetic mono-, di-, and trisubstituted nitroiminotetrazoles. , 2009, Angewandte Chemie.

[8]  B. Twamley,et al.  The synthesis of di(aminoguanidine) 5-nitroiminotetrazolate: some diprotic or monoprotic acids as precursors of energetic salts. , 2008, Chemistry.

[9]  T. Klapötke,et al.  Nitrogen-Rich Salts of 1-Methyl-5-nitriminotetrazolate : An Auspicious Class of Thermally Stable Energetic Materials , 2008 .

[10]  T. Klapötke,et al.  Nitration Products of 5‐Amino‐1H‐tetrazole and Methyl‐5‐amino‐1H‐tetrazoles – Structures and Properties of Promising Energetic Materials , 2007 .

[11]  S. Eliseeva,et al.  5-Nitroaminotetrazole as a building block for extended network structures: Syntheses and crystal structures of a number of heavy metal derivatives , 2007 .

[12]  T. Klapötke,et al.  Copper Bis(1‐methyl‐5‐nitriminotetrazolate): A Promising New Primary Explosive , 2007 .

[13]  C. Ye,et al.  Computational Characterization of Energetic Salts , 2007 .

[14]  B. Twamley,et al.  Energetic Salts of 3-Nitro-1,2,4-triazole-5-one, 5-Nitroaminotetrazole, and Other Nitro-Substituted Azoles† , 2007 .

[15]  Philipp Holzer,et al.  Click chemistry in materials synthesis. 1. Adhesive polymers from copper‐catalyzed azide‐alkyne cycloaddition , 2004 .

[16]  D. V. Davydov,et al.  A Convenient Synthesis of Bis(aminooxy)methane Dihydrochloride , 2004 .

[17]  T. Brill,et al.  Thermal decomposition of energetic materials: Part 80. Pyrolysis of 5-nitraminotetrazole salts of group 1 metals and DFT analysis of the volatile MNCO product (M = Li+, Na+, K+, Rb+, Cs+) , 2002 .

[18]  L. Glasser,et al.  Lattice potential energy estimation for complex ionic salts from density measurements. , 2002, Inorganic chemistry.

[19]  D. Chavez,et al.  Synthesis of the bi-heterocyclic parent ring system 1,2,4-triazolo[4,3-b][1,2,4,5]tetrazine and some 3,6-disubstituted derivatives , 1998 .

[20]  T. Ha,et al.  Ab initio calculation of the thermochemical properties of polysulphanes (H2Sn) , 1998 .

[21]  R. M. Herbst,et al.  Synthesis and Characterization of Nitraminotetrazoles1 , 1957 .