Dimethoxycarbonyl Groups Surrounding a Symmetric Diaminobistetrazole Ring: Exploring New Green Energetic Materials

Article abstract of DOI:10.1002/asia.201901271

A novel oxygen-containing dimethoxycarbonyl diaminobistetrazole (1) was synthesized via a facile strategy. The sodium salt (2) based on this ligand was prepared and these two compounds were fully characterized by using elemental analysis, IR and mass spectrometry and single-crystal X-ray diffraction. Their density, heats of formation, thermal stability and sensitivity, as well as the energetic properties from EXPLO5 code were investigated. These newly synthesized compounds possess high positive heats of formation and detonation heats. Compound 1 exhibits good detonation performance and acceptable stability, and might be a potential eco-friendly alternative of lead azide. The present study contributes to the development of tetrazole derivatives as new energetic materials.

Full text of DOI:10.1002/asia.201901271

DOI: 10.1002/asia.201901271
Communication
Dimethoxycarbonyl Groups Surrounding a Symmetric
Diaminobistetrazole Ring: Exploring New Green Energetic
Materials
[a]
[a]
[b]
[c]
[c]
Piao He,* Jiahao Liu, Jinting Wu, Haozheng Mei, and Jianguo Zhang
nitrogen content and heats of formation, thus exhibit better
stability and explosive performance (Figure 1).
Abstract: A novel oxygen-containing dimethoxycarbonyl
diaminobistetrazole (1) was synthesized via a facile strat-
egy. The sodium salt (2) based on this ligand was pre-
pared and these two compounds were fully characterized
by using elemental analysis, IR and mass spectrometry
and single-crystal X-ray diffraction. Their density, heats of
formation, thermal stability and sensitivity, as well as the
energetic properties from EXPLO5 code were investigated.
These newly synthesized compounds possess high posi-
tive heats of formation and detonation heats. Com-
pound 1 exhibits good detonation performance and ac-
ceptable stability, and might be a potential eco-friendly al-
ternative of lead azide. The present study contributes to
the development of tetrazole derivatives as new energetic
materials.
The methoxycarbonyl is an important kind of organic
groups, and its derivatives can be used as intermediates in
[19,20]
pesticides, medicines and organic synthesis.
In addition,
the high oxygen content in the molecule could contribute to
[21]
the good oxygen balance (OB), which is a key indicator for
evaluating the energy of an explosive. However, the chemistry
of methoxycarbonyl introduced in energetic materials remains
unexplored so far. Thus incorporating this oxygen-containing
group into the bistetrazole skeleton to improve the overall
performance will be of interest as well as challenge.
In a continuing effort to develop new eco-friendly energetic
materials, we directed our attention to design and synthesis of
tetrazole-based derivatives. In this work, a novel dimethoxycar-
bonyl diaminobistetrazole and its sodium salt were readily syn-
thesized firstly. All new compounds were fully characterized by
elemental analysis, IR and mass spectrometry and single-crystal
X-ray diffraction analysis. And their physicochemical and ener-
getic properties were studied as well. The present study con-
tributes to the tetrazole system and provides a new insight in
the design and synthesis of new energetic materials.
Energetic materials play an important role in both military and
civilian applications because they are well-known used as all
[
1,2]
kinds of explosives, propellants and pyrotechnics.
As typical
[3]
examples of high nitrogen-containing energetic compounds,
the development of tetrazoles and their derivatives has been
rapidly benefiting from the efforts of synthetic and theoretical
[
4–9]
Syntheses
researchers over the past few years.
These tetrazoles have
characteristics of large number of NN and CN bonds, deriving
most of their energy from the high positive heats of formation
rather than from the oxidation of the carbon backbone in tra-
ditional energetic compounds. This high nitrogen content also
leads to high densities, and the low amount of carbon and hy-
drogen, which allows for a good oxygen balance to be ach-
The synthesis pathways of dimethoxycarbonyl diaminobistetra-
zole (1) and its sodium salt (2) are shown in Scheme 1. The
commercially available methyl carbazate was reacted with
glyoxal, NCS, and sodium azide in sequence at room tempera-
ture, then the obtained solid was stirred in diethyl ether with
[
10]
ieved more easily. Compared to the mono-tetrazole, the bis-
[
11–18]
tetrazoles
have additional advantages owing to the higher
[a] P. He, J. Liu
College of Chemistry and Chemical Engineering
Central South University
Changsha 410083, Hunan (P. R. China)
E-mail: piaohe@csu.edu.cn
[b] J. Wu
School of Materials Science and Engineering
Southwest University of Science and Technology
Mianyang 621010, Sichuan (P. R. China)
[c] H. Mei, J. Zhang
State Key Laboratory of Explosion Science and Technology
Beijing Institute of Technology
Beijing 100081 (P. R. China)
Supporting information and the ORCID identification number(s) for the au-
thor(s) of this article can be found under:
https://doi.org/10.1002/asia.201901271.
Scheme 1. Synthetic pathway towards compound 1 and 2.
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Figure 1. Selected bistetrazoles as energetic compounds.
saturated HCl gaseous for three days to get compound 1. The
preparation of sodium salt 2 was achieved by straightforward
metathesis reactions that used 1 with the corresponding base
NaOH. These pure materials were slowly crystallized from
water in a colorless block, and their structures were fully char-
acterized by elemental analysis, mass spectrometry, IR spec-
trometry and single-crystal X-ray diffraction. The crystallo-
graphic data are given in Table S1 (Supporting Information).
(O1ÀC3) and 1.184(2) ꢁ (O2=C2), respectively. The extensive
hydrogen bonded network starts from N5 atom of the imino,
respectively linked to neighboring O2 and N3 atom of the me-
thoxycarbonyl and the tetrazole (N5-H5···O2: 1268, H···O:
2.835(2) ꢁ and N5-H5···N3: 1308, H···N: 3.134(3) ꢁ) (Figure 2b).
These hydrogen bond interactions form a reticular framework
of 1, which could be a key factor for the good thermal stabili-
ty.
Compound 2 crystallizes in the monoclinic P2/c space
group, with two molecules in the unit cell and the asymmetry
unit is composed of two sodium ions and one dimethoxycar-
bonyl diaminobistetrazole anion (Figure 3a). In its anionic
structure, the tetrazole rings show a dihedral angle N1-N2-N3-
N4of 172.6(7)8, and the bond length of connecting bond (C2À
C2) is 1.480(17) ꢁ. The substituted group is also twisted out of
the tetrazole plane (N1-N2-C2-N5 À171.8(8)8). The sodium
center atom is six-coordinated by two oxygen atoms from the
dimethoxycarbonyl with NaÀO bond length of 2.423(6) ꢁ and
four oxygen atoms from the water molecule with bond lengths
Crystal structures
Compound 1 crystallizes in the monoclinic P2(1)/c space group
(Figure 2a), with two molecular moieties in the unit cell and a
À3
density of 1.640 gcm at 298 K. Both of the tetrazole rings
can be considered planar (N1-N2-N3-N4 À0.8(2)8, C1-N1-N2-N3
0.5(2)8), while the methoxycarbonyl shows a certain distortion
of the plane. The C1ÀC1 bond length of the linkage connect-
ing the two tetrazole moieties is 1.450(4) ꢁ and the CO bond
lengths of the substituted group are 1.317(2) (O1ÀC2), 1.444(3)
Figure 2. Crystal structure of the compound 1: (a) molecular unit (b) unit cell view along b axis with hydrogen bonds.
Figure 3. Crystal structure of the compound 2: (a) molecular unit (b) coordination octahedron.
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ranging from 2.371(7) ꢁ to 2.451(7) ꢁ (Figure 3b). This sodium
salt shows a 1D chain structure with alternately assembling
units and an adjacent Na···Na distance of 3.176(3) ꢁ (Na1-Na1).
Table 1. Physiochemical and energetic properties of compounds 1 and 2.
[
24]
[16]
Compound
1
2
TNT
3
Pb(N )
[
a]
IS [J]
1
14
40
360
39
353
À74.0
18.5
295
2.5–4
0.1–1
À11.0
28.9
315
4.8
450.1
1574.9
[
b]
FS [N]
W co
N [%]
dec [8C]
Thermal behavior
[c]
2
[
[%]
À67.5
49.2
191
1.64
325.5
1023.0
À53.6
42.6
102
1.65
232.8
888.5
d]
The thermal behaviors of newly synthesized compounds were
determined using differential scanning calorimetry measure-
[
e]
T
1
À3 [f]
[gcm
]
1.65
À1
À1 [g]
ments (DSC) at a heating rate of 58Cmin . And the summar-
D H 8 [kJmol
]
À67.0
À415.2
f
m
À1 [h]
D
f
U8 [kJkg
EXPLO5 6.01:
ÀDExH8[kJkg
]
ized DSC plot is depicted in Figure 4. Melting points are not
observed both in compound 1 and 2, indicating their direct
exothermic decomposition without the melting process. Com-
pound 1 has an exothermic peak at 1918C, but compound 2
exhibits a lower decomposition temperature of 1028C. This
result shows that the thermal stability of sodium salt decreases
relative to the neutral compound, which is caused by the
strong intermolecular H-bond interactions in 1 compared to 2.
À1 [i]
]
3905
2862
20.1
7403
774
4762
3148
17.5
7041
522
5042
–
19.5
6881
825
1569
3401
33.8
5920
252
[j]
det
T
[
k]
PCJ[GPa]
det[ms ]
[Lkg ]
À1 [l]
V
À1 [m]
V
0
[a] Impact sensitivity. [b] Friction sensitivity. [c] Oxygen balance for CaH-
bOcNd: 1600(c-2a-b/2)/MW. [d] Nitrogen content. [e] Decomposition tem-
perature. [f] Density at RT. [g] Heat of formation. [h] Energy of formation.
[
[
i] Heat of detonation. [j] Detonation temperature. [k] Detonation velocity.
l] Detonation pressure. [m] Volume of detonation gases (assuming only
gaseous products). MW=molecular weight.
and could be its potential alternative from an environmental
point of view.
Computational considerations
To better understand the electronic properties, geometric
structure, HOMO–LUMO orbitals and electrostatic potential
(
ESP) of 1 was calculated using the density functional theory
DFT) with B3LYP/6-31+G** method. Compound 1 shows a bi-
Figure 4. DSC curves at a heating rate of 58C for compound 1 and 2.
(
tetrazole linked by the CÀC bond and two dimethoxycarbonyl
groups twisted out from the tetrazole plane with a torsion
angle (Figure 5a). The optimized geometrical parameters are
similar to the experimental values and tabulated in Table S4.
The HOMO of the molecule is localized both on tetrazole rings
and substituted groups, while the LUMO is distributed on the
rings as well as the C=C bond (Figure 5b). The energy gap be-
Energetic Properties
The energetic Properties of the synthesized compounds were
investigated and the results are summarized in Table 1. Impact
and friction sensitivities were measured by standard BAM tech-
niques and classified according to the “U.N. Recommendations
[
22]
on the Transport of Dangerous Goods”. Compound 1 (IS=1
J, FS=14 N) can be classified as very sensitive and the sodium
salt 2 (IS=40 J; FS=360 N) can be classified as insensitive.
Compounds 1 and 2 have high nitrogen content (exceeding
40%) and negative oxygen balances. The neutral compound 1
exhibits good thermal stability with a decomposition tempera-
ture of 1918C, whereas the metal salt 2 has a higher density of
À3
1
.65 gcm . The results of heats of formation calculated based
on isodesmic reactions indicate that they have positive heats
À1
of formation (325.5 and 232.8 kJmol ) and are significantly
greater than that of TNT. The detonation parameters were cal-
[
23]
culated using the EXPLO5 code using a calculated heat of
formation and density. Both of compounds 1 and 2 show good
À1
detonation heats (3905 and 4762 kJkg ), which are higher
than that of Pb(N ). The calculated detonation velocity (7403
3
À1
and 7041 ms ) and detonation pressure (20.1 and 17.5 GPa)
imply that these new compounds outperform commonly used
explosive TNT. Thereinto, the dimethoxycarbonyl diaminobiste-
trazole (1) is comparable to the primary explosive lead azide
Figure 5. DFT calculations for compound 1: (a) optimized structure
(b) HOMO–LUMO (3) electrostatic potential.
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tween the HOMO and LUMO is 5.54 eV, which shows molecular
stable nature. As can be seen from ESP map (Figure 5c), the re-
gions having the negative potential are over the electronega-
tive oxygen and nitrogen atom, which are preferred sites for
the electrophilic attack indications. The regions having the
positive potential are over the hydrogen atom, which are pre-
ferred sites for the nucleophilic attack symptoms.
stirred overnight at room temperature, then was diluted with
3
0 mL of ice-water and filtered to get the diazido product. This
solid was suspended in 50 mL of diethyl ether with saturated HCl
gaseous cooled with an ice bath at 58C. The flask was sealed and
stirred at room temperature for three days. The solvent was re-
moved and the solid recrystallized from methanol yielding new
compound 1 as colorless plates.
À1
DSC (58Cmin ): 1918C (dec); IR (KBr): n˜ =3413 (m), 3472 (w), 3220
In summary, we prepared a novel dimethoxycarbonyl diami-
nobistetrazole in a straightforward manner. Computational
analysis was used to reveal the stability and electronic proper-
ties of this new molecule. The sodium salt based on this ligand
was also synthesized and these two compounds were fully
characterized by elemental analysis, IR spectroscopy, mass
spectrometry and single-crystal X-ray diffraction. Compound 1
shows a reticular network with hydrogen bond interactions,
and compound 2 features a 1D framework structure benefiting
from the characteristic coordination modes. Their thermal sta-
bilities were determined by DSC, and the energetic properties
were evaluated by the EXPLO5 code as well as the BAM test.
Both of them exhibit high heats of formation (up to
(
2
m), 3170 (m), 3133 (m), 3005 (w), 2956 (w), 2544 (w), 2326 (w),
252 (w), 2158 (s), 2135 (s), 1704 (s), 1598 (s), 1528 (w), 1469 (s),
1345 (s), 1194 (w), 1153 (s), 1085 (s), 1014 (m), 881 (w), 786 (w), 764
(m), 683 (m), 663 (w), 608 (m), 574 (w), 547 (m), 511 cm (m); MS
(
2
À1
À
ESI ): m/z: 285.08 (C H N O ); EA: calc: C 25.36%, N 49.29%,
6
8
10
4
.84%; found: C 25.75%, N 50.42%, 2.87. BAM drop hammer: 1 J;
friction tester: 14 N.
Sodium dimethoxycarbonyl diaminobistetrazolate (2)
Powdered colorless 1 (0.28 g, 1 mmol) was dissolved in the deion-
ized water, and sodium hydroxide (0.08 g, 2 mmol) was added.
After the mixture had been stirred several minutes, the filtrate was
slowly evaporated to leave the solid product 2 as colorless blocks.
À1
À1
À1
DSC (58Cmin ): 1028C (dec); IR (KBr): n˜ =3440 (s), 3013 (w), 2955
(
(
(
325.5 kJmol ) and detonation heats (up to 4762 kJkg ). The
w), 2920 (w), 2850 (w), 2138 (m), 2108 (m), 1708 (s), 1581 (s), 1540
s), 1446 (s), 1351 (w), 1313 (s), 1196 (w), 1157 (w), 1105 (w), 1072
m), 1004 (m), 879 (w), 823 (w), 767 (w), 693 (w), 640 (w), 611 (w),
detonation performance of 1 is higher than that of the primary
explosive lead azide and might serve as its eco-friendly alterna-
tive.
À1
À
5
74 (w), 548 (w), 463 (w), 420 cm (w); MS (ESI ): m/z: 285.1
2À
(C H N O ); EA: calc: C 21.96%, N 42.68%, 1.84%; found: C
6 6 10 4
2
1.93%, N 42.66%, 1.82%. BAM drop hammer: 40 J; friction
Experimental Section
tester: 360 N.
General procedures
Computational Details
All chemical reagents and solvents were obtained from Sinopharm
Chemical Reagent Co., Ltd. Decomposition point was determined
by differential scanning calorimetry (DSC) on a model Pyris-1 at a
The geometric optimization and frequency analyses were carried
out by using B3LYP functional
[
27–29]
analyses with the 6-31+G**
À1
heating rate of 58Cmin . Infrared spectra were recorded on a
basis set. The optimized structures were characterized as true local
energy minima on the potential energy surface without imaginary
frequencies. The electrostatic potential and HOMO–LUMO orbitals
were calculated at the same level of theory based on the opti-
mized structures. Single energy points were calculated at the MP2/
6-311+ +G** level. All computations were performed by using the
Bruker Equinox 55 spectrometer. Mass spectra of the described
compounds were measured at a Agilent 500-MS. Elemental analysis
was performed on an Elementar Vario El III analyzer. The impact
and friction sensitivities were performed on a BAM fall hammer
BFH-10 and a BAM friction apparatus FSKM-10, respectively. Collec-
tion of XRD data was performed on a Rigaku Saturn 724+ CCD dif-
fractometer equipped with graphite monochromatized MoKa radia-
tion. The structure was solved by using direct methods and succes-
sive Fourier difference syntheses (SHELXS-97) were refined by
using full-matrix least-squares on F2 with anisotropic thermal pa-
rameters for all non-hydrogen atoms (SHELXL-97).
atoms were added theoretically and refined with riding model po-
sition parameters and fixed isotropic thermal parameters.
[30]
Gaussian 09 suites of programs.
[25]
Acknowledgements
[26]
Hydrogen
The supports of the Central South University Science Research
Initial Fun and the opening project of State Key Laboratory of
Explosion Science and Technology (Beijing Institute of Technol-
ogy) (KFJJ19-07M) are gratefully acknowledged.
CCDC 1492730 (1) and 1492731 (2) contain the supplementary
crystallographic data for this paper. These data are provided free
of charge by The Cambridge Crystallographic Data Centre.
Conflict of interest
Dimethoxycarbonyl diaminobistetrazole (1)
The authors declare no conflict of interest.
The commercially available methyl carbazate (4.50 g, 50 mmol) was
reacted with the glyoxal (1.45 g, 25 mmol) at room temperature to
get the dimethoxycarbonylglyoxal bishydrazone. Then this com-
pound was suspended in 300 mL DMF, added the NCS (20 g,
Keywords: detonation performance
· DFT calculations ·
dimethoxycarbonyl diaminobistetrazole · energetic materials
1
50 mmol) and the mixture was stirred overnight at room temper-
ature and filtered to obtain the dichloro product. This dichloro
product was suspended in 10 mL DMF and cooled to 0–58C with
the sodium azide (650 mg, 10 mmol) added. The mixture was
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Version of record online: && &&, 0000
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Communication
COMMUNICATION
Piao He,* Jiahao Liu, Jinting Wu,
Haozheng Mei, Jianguo Zhang
&& – &&
Dimethoxycarbonyl Groups
Surrounding a Symmetric
Diaminobistetrazole Ring: Exploring
New Green Energetic Materials
An oxygen-containing dimethoxycar-
bonyl diaminobistetrazole and its
of experimental and computational
methods. This compound exhibits good
detonation performance and acceptable
stability, and might be a potential eco-
friendly alternative of lead azide.
sodium salt were synthesized and fully
characterized. Their properties were ex-
tensively investigated by a combination
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ꢀ 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
ÝÝ These are not the final page numbers!