cas 127661-01-2, N,N-Bis[1(2)H-tetrazol-5-yl]amine

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Chlorine anion-π and π--π- interactions in two tetrazolyl derivative based Cu2+ complexes and quantum chemical calculations
Two bis(tetrazolyl)amine (H2BTA) and 5,5′-azotetrazolate (AT) based Cu2+ supramolecular complexes [Cu(H2BTA)Cl 2(H2O)]·2H2O (1) and [Cu 2(AT)2(pn)3]·2H2O (2) (pn = 1,3-diaminopropane) have been synthesized and characterized by single crystal X-ray diffraction analysis. In 1, each Cu2+ ion displays a tetragonal pyramidal structure and an anion-π of Cl--π interaction has been observed. The Cl--π binding interaction together with O-H?Cl, N-H?Cl, N-H?O and O-H?N four hydrogen bonds link the complex units and lattice water molecules to form a 3D supramolecular network structure. In 2, the Cu2+ ions show an elongated octahedral structure and a 1D chain structure bridged by μ2-trans-AT 2- ligands is found. An unusual face-to-face π-- π- stacking interaction between trans-AT2- anions in 2 is found. Complex 2 also exhibits a 3D supramolecular structure in which the π--π- stacking, O-H?N and N-H?O hydrogen bonding and electrostatic interactions are responsible for the stabilization of the complex. The aqueous solution of 2 shows photochromic property. The Cl--π and π--π- interaction energies in 1 and 2 were calculated at MP2 level using gaussian 09 suite and demonstrated.
Li, Nan,Chen, Wen-Bin,Guan, Yang-Fan,Ouyang, Zhen-Jie,Dong, Wen
p. 349 - 352
(2014)
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Energetic salts based on monoanions of N,N-Bis(lH-tetrazol-5-yl)amine and 5,5'-Bis(tetrazole)
High-density energetic salts that contain nitrogen-rich cations and the 5-(tetrazol-5-ylamino)tetrazolate (HBTA-) or the 5-(tetrazol-5-yl) tetrazolate (HBT-) anion were readily synthesized by the metathesis reactions of sulfate salts with barium compounds, such as bis[5-(tetrazol-5- ylamino)tetrazolate] (Ba(HBTA)2), barium iminobis(5-tetrazolate) (BaBTA), or barium 5,5'-bis(tetrazolate) (BaBT) in aqueous solution. All salts were fully characterized by IR spectroscopy, multinuclear (1H, 13C, 15N) NMR spectroscopy, elemental analyses, density, differential scanning calorimetry (DSC), and impact sensitivity. Ba(HBTA) 24H2O crystallizes in the triclinic space group P1, as determined by single-crystal Xray diffraction, with a density of 2.1.77 gcm -3. The densities of the other organic energetic salts range between 1.55 and 1.75 gem-3 as measured by a gas pycnometer. The detonation pressure (P) values calculated for these salts range from 19.4 to 33.6 GPa, and the detonation velocities (vD) range from 7677 to 9487 ms-1, which make them competitive energetic materials. Solid-state 13CNMR spectroscopy was used as an effective technique to determine the structure of the products that were obtained from the metathesis reactions of biguanidinium sulfate with barium iminobis(5-tetrazolate) (BaBTA). Thus, the structure was determined as an HBTA salt by the comparison of its solid-state 13C NMR spectroscopy with those of ammonium 5(tetrazol-5-ylamino)tetrazolate (AHBTA) and diammonium iminobis(5-tetrazolate) (A2BTA).
Guo, Yong,Tao, Guo-Hong,Zeng, Zhuo,Gao, Haixiang,Parrish, Damon A.,Shreeve, Jean'ne M.
p. 3753 - 3762
(2010)
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Bistetrazolylamines - Synthesis and characterization
The acid-catalyzed cyclization reaction of sodium dicyanamide and sodium azide in the ratio of 1: 2 afforded 5,5′-bis(1H-tetrazolyl)amine (H 2bta, 2) in high yield (88%) as the monohydrate. Dehydration of 2·H2O at elevated temperatur
Klapoetke, Thomas M.,Mayer, Peter,Stierstorfer, Joerg,Weigand, Jan J.
p. 5248 - 5258
(2008)
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High-temperature spin crossover behavior in a nitrogen-rich Fe III-based system
A nitrogen-rich ligand bis(1H-tetrazol-5-yl)amine (H3bta) was employed to isolate a new FeIII complex, Na2NH 4[FeIII(Hbta)3]·3DMF·2H 2O (1). Single crystal X-ray diffraction revealed that complex 1 consists of FeIII ions in an octahedral environment where each metal ion is coordinated by three Hbta2- ligands forming the [Fe III(Hbta)3]3- core. Each unit is linked to two one-dimensional (1-D) Na+/solvent chains creating a two-dimensional (2-D) network. In addition, the presence of multiple hydrogen bonds in all directions between ammonium cation and ligands of different [Fe III(Hbta)3]3- units generates a three-dimensional (3-D) network. Magnetic measurements confirmed that the FeIII center undergoes a Spin Crossover (SCO) at high temperature (T1/2 = 460(10) K).
Cook, Cyril,Habib, Fatemah,Aharen, Tomoko,Clerac, Rodolphe,Hu, Anguang,Murugesu, Muralee
p. 1825 - 1831
(2013)
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Tetranuclear complexes composed of dinickel(II) macrocyclic fragments bridged by 5,5′-(1,3-phenylene)bis-1H-tetrazolato and N,N-bis(tetrazol-5- ato)amine coligands: Synthesis, structures and magnetic properties
The dinuclear nickel(II) complex [Ni2LCl]+, where L2- represents a 24-membered macrocyclic hexamine-dithiophenolate ligand, reacts with 5,5′-(1,3-phenylene)bis-1H-tetrazole and N,N-bis(tetrazol-5-yl)amine to give the tetranuclear complexes [(Ni 2L)2(N4C-X-CN4)]+, where X = 1,3-C6H4 (1) and NH (2). The new complexes were both isolated as perchlorate or tetraphenylborate salts and characterized by elemental analysis, UV/Vis, IR spectroscopy, and X-ray analysis. The crystal structures of the tetraphenylborate salts show bridging bistetrazolato moieties joining two dinuclear [Ni2L]2+ fragments through their ring N2 and N3 atoms. Temperature-dependent magnetic susceptibility measurements reveal the presence of weak ferromagnetic exchange interactions between the NiII ions in the binuclear [Ni2L]2+ subunits with magnetic exchange coupling constant values of J1 = 16.6 cm -1 for 1[BPh4]2, and J1 = 16.8 cm-1 for 2[BPh4]2 (H = -2JS1S 2). The exchange coupling constant J2 across the bistetrazolato bridge in both compounds is less than 0.1 cm-1, which suggests that no significant interdimer coupling occurs across the linking tetrazolato moieties.
Lach, Jochen,Mosalkova, Anastasiya P.,Voitekhovich, Sergei V.,Gaponik, Pavel N.,Kersting, Berthold
p. 183 - 189
(2013)
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Nitrogen-rich energetic ionic liquids based on the N,N-Bis(1H-tetrazol-5- yl)amine anion - Syntheses, structures, and properties
N,N-Bis(1H-tetrazol-5-yl)amine anions (HBTA-/BTA2-) were used as suitable nitrogen-rich components for the construction of energetic ionic liquids. Seven ionic liquids, namely, 1,3-dimethylimidazolium (1, [C 1mim]HBTA), 1-ethyl-3-methylimidazolium (2, [C2mim]HBTA), 1-butyl-3-methylimidazolium (3, [C4mim]HBTA), 1-hexyl-3- methylimidazolium (4, [C6mim]HBTA), 1-methyl-3-octylimidazolium (5, [C8mim]HBTA), and 1,2,3-trimethylimidazolium (6, [C 1mmim]HBTA) cations with the HBTA- anion and di-1,2,3-trimethylimidazolium N,N-bis(1H-tetrazol-5-yl)amine (7, [C 1mmim]2BTA), were synthesized. All materials were fully characterized by IR and NMR spectroscopy, elemental analysis, and high-resolution mass spectrometry. The crystal structures of 1 and 7 were determined by single-crystal X-ray diffraction [1: monoclinic, P21/n, a = 14.0653(4) A, b = 6.9507(2) A, c = 22.4699(7) A, β = 93.996(3)°, V = 2191.38(12) A3, Z = 8, ρ = 1.511 g cm-3; 7: monoclinic, P21/c, a = 17.5869(3) A, b = 12.8757(2) A, c = 21.9203(6) A, β = 125.0580(10)°, V = 4063.15(15) A3, Z = 8, ρ = 1.221 g cm-3]. The nitrogen contents of 1-7 exceed 40 %, and 1 has the highest value of 61.78 %. The ionic liquids 1-7 are thermally stable to 220 °C, and 2-5 are room-temperature ionic liquids. The heats of formation of 1-7 obtained by both experimental and theoretical methods are all positive. The ionic liquids 1-7 are insensitive towards impact (>40 J) and friction (>360 N). They can be ignited in air. These new energetic ionic liquids contain only C, H, and N and are of interest as potential propellants with high energy, high thermal stability, low sensitivity to impact and friction, and environmentally friendly decomposition gases. Nitrogen-rich energetic ionic liquids based on the N,N-bis(1H-tetrazol-5-yl)amine anion were synthesized. These ionic liquids have high nitrogen contents, high heats of formation, and high stabilities to heat, impact, and friction. These nitrogen-rich energetic ionic liquids combust in air after ignition with a flame. They are potential environmentally friendly liquid propellants. Copyright
Dong, Lin-Lin,He, Ling,Liu, Hang-Yu,Tao, Guo-Hong,Nie, Fu-De,Huang, Ming,Hu, Chang-Wei
p. 5009 - 5019
(2013)
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Synthesis, structure, magnetic properties and DFT calculations of novel bis-(5-tetrazolyl)amine copper(II) complexes
Four new multidimensional copper(II) complexes [Cu(BTA)(2,2′-bipy) H2O] (1), [Cu(BTA)(1,10′-phen)] (2), [Cu2(BTA) 2(H2O)4] (3) and [Cu(BTA)(en)]n (4) have been synthesized by conventional and hydrothermal reactions of the bis(5-tetrazolyl)amine (H2BTA) with copper(II) salts in the presence of different ancillary ligands. X-ray diffraction studies on these compounds show 1 and 2 are mononuclear entities, in which the BTA ligand acts in a chelate coordination mode and the copper atoms exhibit a coordination environment intermediate between trigonal-bipyramidal and square-pyramidal for 1 and between square-planar and tetrahedral for 2. Complex 3 consists of centrosymmetric dinuclear molecules with the ligand acting in a μ2-1,1′:2 chelate/bridging tridentate coordination mode and 4 is a linear zigzag neutral chain bearing a BTA bridging ligand in a μ2-1,1′:3 chelate/bridging tridentate coordination mode. Complexes 3 and 4 exhibit antiferromagnetic and very weak ferromagnetic interactions, respectively. DFT calculations have been performed in order to explain their respective magnetic behaviors.
Rodriguez-Dieguez, Antonio,Lopez-Viseras, Marta E.,Perea-Buceta, Jesus E.,Mota, Antonio J.,Colacio, Enrique
p. 73 - 80
(2012)
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PROCESS FOR THE PREPARATION OF BIS-(1(2)H-TETRAZOL-5-YL)-AMINE MONOHYDRATE
A process for the preparation of Bis-(1(2)H-tetrazol-5-yl)-amine monohydrate. This preparation process is carried out by the reaction between sodium dicynamide and sodium azide in presence of a dilute solution of an inorganic acid solution in aqueous medium.
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(2014/03/25)

Amine salt-catalyzed synthesis of 5-substituted 1H-tetrazoles from nitriles
The [3+2] cycloaddition reaction between sodium azide and various organic nitriles proceeds smoothly in the presence of amine salts as catalyst in dimethylformamide. The corresponding 5-substituted 1-H tetrazoles were obtained under mild condition in good to excellent yields. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Taylor & Francis Group, LLC.
Zhou, Yi,Yao, Cheng,Ni, Renjie,Yang, Gaowen
experimental part
p. 2624 - 2632
(2010/10/03)

BIS-(1(2)H-TETRAZOL-5-YL)AMINE AND PRODUCTION METHOD THEREFOR
High-quality bis-(1(2)H-tetrazol-5-yl)amine and a method for easily, safely, and inexpensively producing the compound are provided. The method for producing bis-(1(2)H-tetrazol-5-yl)amine includes the steps of heating to 50 to 120° C. a solution mixture in which a necessary amount of an azide salt and a dicyanamide salt in an amount corresponding to 1 to 80 wt % of a necessary amount are added to a solvent, adding an acid in an amount of 1.54 to 2.22 chemical equivalents of the dicyanamide salt in the solution mixture to carry out a reaction at 50 to 120° C., and then adding an acid and a dicyanamide salt solution in which the remaining dicyanamide salt is dissolved in a solvent to promote the reaction. Bis-(1(2)H-tetrazol-5-yl)amine is obtained according to the production method.
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(2010/11/03)

BIS-(1(2) H-TETRAZOL-5-YL)-AMINE MONOHYDRATE SYNTHESIS AND REACTION INTERMEDIATE
The present invention provides Bis-(1(2)H-tetrazol-5-YL)-amine compound, and safe and inexpensive methods for producing high quality Bis-(1(2)H-tetrazol-5-YL)-amine compound. Also provided are Bis-(1(2)H-tetrazol-5-YL)-amine intermediates, and methods for their preparation. The process of preparing Bis-(1(2)H-tetrazol-5-YL)-amine intermediate substantially combines dicyanamide salt, azide salt, solvent and acid at 40-70 C temperature. The process of preparing Bis-(1(2)H-tetrazol-5-YL)-amine anhydride and/or Bis-(1(2)H-tetrazol-5-YL)-amine monohydrate comprises heating the intermediate described above at ≧75 C and adding a second acid.
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(2008/12/08)

Synthesis and thermal decomposition of ditetrazol-5-ylamine
Ditetrazol-5-ylamine (DTA) was synthesized from cyanuric chloride in four steps. The thermal decomposition of DTA in the solid state was studied by thermogravimetry, volumetry, mass spectrometry, IR spectroscopy, and calorimetry. Under isothermal conditions at 200-242°C, thermal decomposition obeys the first order autocatalytic kinetics. The kinetic and activation parameters of DTA decomposition were determined. The composition of gaseous reaction products and the structure of condensed residue were studied. The thermal effect of thermal DTA decomposition is 281.4 kJ mol-1. The nitrogen content in a mixture of gaseous products formed by the reaction in a temperature interval of 200-242°C exceeds 97 vol.%.
Nedel'ko,Shastin,Korsunskii,Chukanov,Larikova,Kazakov
p. 1710 - 1714
(2007/10/03)

Products of Reactions of Azido Derivatives of s-Triazine with Some O- and N-Nucleophiles
The mobility of the azido group in alkoxy derivatives of s-triazine in reactions with some O- and N-nucleophiles has been studied.Reactions of azidoalkoxy-s-triazines with ammonia gave products of substitution of both the azido and alkoxy groups.In reactions of azido-s-triazines with hydrazines, replacement of the azido group is accompanied by transformation of the triazine ring to give triazolylaminotetrazoles.Acid hydrolysis of diazidoalkoxy derivatives yields cyanuric acid as a result of substitution of both the azido and alkoxy groups.When diazidoalkoxy-s-triazines are heated in water in the absence of an acid, transformations of the triazine ring occurs with formation of bis(5-tetrazolyl)amine.
Azev, Yu. A.,Gusel'nikova, O. L.,Klyuev, N. A.,Shorshnev, S. V.,Rusinov, V. L.,Chupakhin, O. N.
p. 1418 - 1424
(2007/10/03)