Improved Synthesis and Thermochemical Properties of Amino- and Hydrazino-1,2,4,5-Tetrazines

Article abstract of DOI:10.1007/s10593-020-02836-9

[Figure not available: see fulltext.] Improved protocols for the synthesis of 3,6-diamino- and 3,6-dihydrazino-1,2,4,5-tetrazines as well as 6-amino[1,2,4]triazolo[4,3-b]-[1,2,4,5]tetrazine were developed. Combustion energies were determined by the bomb calorimetry and the enthalpies of formation in the standard state were calculated for the compounds of this study. Based on the obtained data, the contribution of the 1,2,4,5-tetrazine moiety to the enthalpy of combustion of its derivatives was estimated.

Full text of DOI:10.1007/s10593-020-02836-9

DOI 10.1007/s10593-020-02836-9
Chemistry of Heterocyclic Compounds 2020, 56(11), 1449–1453
Improved synthesis and thermochemical properties
of amino- and hydrazino-1,2,4,5-tetrazines
Tat'yana S. Kon'kova1*, Yurii N. Matyushin1, Evgeniy А. Miroshnichenko1,
Nadezhda V. Palysaeva2, Aleksei B. Sheremetev2*
1 N. N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences,
4 Kosygina St., Moscow 119991, Russia; е-mail: taskon@mail.ru
2 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,
47 Leninsky Ave., Moscow 119991, Russia; е-mail: sab@ioc.ac.ru
Submitted August 17, 2020
Accepted after revision October 5, 2020
Translated from Khimiya Geterotsiklicheskikh Soedinenii,
2020, 56(11), 1449–1453
Improved protocols for the synthesis of 3,6-diamino- and 3,6-dihydrazino-1,2,4,5-tetrazines as well as 6-amino[1,2,4]triazolo[4,3-b]-
[1,2,4,5]tetrazine were developed. Combustion energies were determined by the bomb calorimetry and the enthalpies of formation in the
standard state were calculated for the compounds of this study. Based on the obtained data, the contribution of the 1,2,4,5-tetrazine moiety to
the enthalpy of combustion of its derivatives was estimated.
Keywords: 1,2,4,5-tetrazine, calorimetry, enthalpy of combustion, enthalpy of formation.
Precise experimental values of the enthalpies of
formation (ΔHf) of compounds of various classes
undoubtedly form the basis of fundamental thermo-
chemistry and are also of great importance for applied
science. Unfortunately, experimental values are available
for less than 0.1% of known compounds. Since the
experimental determination of thermochemical characteris-
tics is a very laborious process, significant efforts are spent
on the development of computational approaches. Various
empirical and semiempirical methods require extensive
parametrization and often lead to significant errors in the
assessment of atypical molecules, in particular energy-rich
molecules which are components of energetic materials
(explosives, propellants, pyrotechnic compositions).
When assessing the potential value of an energetic
compound, the key performance indicators are usually the
detonation velocity and pressure for explosives, and the
specific impulse for propellants. The basic characteristic
that determines these properties is the energy that is
released during detonation or combustion which can be
easily estimated by calculation methods1 if the heat of
formation of the compound ΔHf is known.2 The
decomposition energy is also related to the sensitivity of
energetic compounds to the initiation of detonation3
characterizing the risks of their use. Only having a reliable
ΔHf value the performance and the safety of using an
energetic compound can be correctly assessed.
High nitrogen heterocycles are the most promising and
environmentally attractive building blocks for designing
new energetic compounds. Indeed, compounds with a high
nitrogen content are characterized by high energy content,
and their decomposition is accompanied by the release of a
large amount of heat and the formation of environmentally
friendly molecular nitrogen as the main product of
destruction.4
In recent years, the possibilities for the design of
energetic compounds based on 1,2,4,5-tetrazine have been
demonstrated.5 However, the information available in the
literature on the experimentally measured values of the
enthalpies of formation of derivatives of this heterocycle is
very scarce.6 Here, the results of a thermochemical study of
three tetrazine derivatives: 3,6-diamino-1,2,4,5-tetrazine
(1), 3,6-dihydrazinyl-1,2,4,5-tetrazine (2) (Scheme 1), and
6-amino[1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine (3) (Scheme 2),
already widely used5 in the practical chemistry of energetic
compounds are described.
0009-3122/20/56(11)-1449©2020 Springer Science+Business Media, LLC
1449

Chemistry of Heterocyclic Compounds 2020, 56(11), 1449–1453
Scheme 1
hydrazine hydrate, both nitropyrazole moieties were
instantly substituted at room temperature and 3,6-
dihydrazinyl-s-tetrazine (2) was formed in quantitative
yield (Scheme 1).
Me
NO2
Me
Me
N
N
Me
N
N
The synthesis route for compound 3 was also simplified
(Scheme 2). The most problematic step in the synthesis of
compound 3 is the 1,2,4-triazole ring closure which leads
to the formation of the bicyclic product 7. Earlier, expensive
diethoxymethyl acetate was used to cyclize the readily
available monohydrazinyl derivative 6, and, as a result of
heating the reaction mixture under reflux for 5 min,
compound 7 was formed in 93% yield.10 Later it was
reported that heating monohydrazine 6 with an excess of
cheaper triethyl orthoformate under reflux for 3 h affords
product 7 in 72% yield.11 We have shown that the addition
of trifluoroacetic acid to triethyl orthoformate makes it
possible to carry out the reaction at room temperature in 1 h
(70% yield), whereas at 70°C it is complete in 5 min leading
to product 7 in 94% yield. The substitution of the pyrazole
moiety of compound 7 was carried out according to the
literature method in boiling EtOH using 30% aqueous
ammonia, which made it possible to obtain crude
compound 3 in 77% yield in 2 h.10 Analytically pure
sample 3 was obtained in 58% yield.
HNO3, (CF3CO)2O
N
N
N
N
N
N
N
N
MeCN, –30°C rt
98%
N
N
Me
O2N
Me
N
N
Me
Me
4
5
NH4OH
NH3
MeO(CH2)2OMe
N2H4 H2O
MeO(CH2)2OMe
rt, 5 min
NMP
rt, 1 h
100%
98%
10 atm
97%
90°C, 6 h
N
N
N
N
N
H2N
HN
N
H2N
NH
NH2
NH2
N
N
1
2
We measured the combustion energies of compounds 1–3
by bomb calorimetry and calculated the enthalpies of their
formation in the standard state. Based on the obtained
thermochemical data, the contribution of the 1,2,4,5-
tetrazine moiety to the enthalpy of combustion of its
derivatives was calculated. Note that obtaining precision
experimental values of the standard enthalpies of formation
in the solid phase ∆Hºf(cr), complementing the existing
database, makes it possible to increase the accuracy of
estimating the enthalpies of formation of hypothetical
analogs by the group contribution method, which combines
simplicity and reliability.
Scheme 2
Despite the fact that compounds 1–3 have been known
for a long time, the methods of their synthesis are not
effective or use expensive reagents. We began our studies
by developing more effective synthetic protocols. The most
widely used precursor in the synthesis of 1,2,4,5-tetrazine
derivatives (also called s-tetrazine) is 3,6-bis(3,5-
dimethylpyrazol-1-yl)-s-tetrazine (4).7
The dimethylpyrazolyl groups of compound 4 can be
replace by the action of various nucleophiles which is
widely employed in organic synthesis to obtain tetrazine-
containing compounds.8 It is known that the introduction of
an electron-withdrawing moiety, such as a bromine or
chlorine atom, into position 4 of the pyrazole facilitates the
substitution of this modified substituent with nucleophiles.9
Assuming that the presence of a nitro group in the pyrazole
ring will further increase the nucleofugicity of the leaving
group, we synthesized nitro derivative 5 by treating
compound 4 with a mixture of 100% HNO3 and trifluoro-
acetic anhydride (Scheme 1).
As is known, the substitution of two pyrazole moieties in
tetrazine 4 with amino groups proceeds only at treatment
with an excess of NH3 in N-methylpyrrolidone (NMP) at
90°С in an autoclave under pressure (10 atm) for 6 h.7 We
found that the substitution of the nitropyrazole moiety of
compound 5 is easily accomplished with an excess of
aqueous NH3 in glyme at room temperature and ordinary
pressure for 1 h, giving diamine 1 in 97% yield (Scheme 1).
When a solution of compound 5 in glyme was treated with
The developed methods scale up well, which allows one
to obtain the compounds of this study in the required
quantities. For thermochemical study, the samples were
purified by repeated recrystallization and vacuum drying.
The structures and purity of the synthesized compounds
1
were confirmed by H and 13C NMR spectroscopy, mass
spectrometry, and elemental analysis.
The energies of combustion as measured by bomb
calorimetry for the compounds of this study are given in
Table 1. Reactions of combustion of compounds 1–3
proceed in accordance with the stoichiometry presented by
equations (1)–(3), respectively:
C2H4N6(cr) + 3O2(g) = 2CO2(g) + 2H2O(l) + 3N2(g)
C2H6N8(cr) + 3.5O2(g) = 2CO2(g) + 3H2O(l) + 4N2(g)
C3H3N7(cr) + 3.75 O2(g) = 3CO2(g) +1.5H2O(l) + 3.5N2(g)
,
(1)
(2)
(3)
,
,
where the subscripts cr, g, and l correspond to the
crystalline, gaseous, and liquid states, respectively.
1450

Chemistry of Heterocyclic Compounds 2020, 56(11), 1449–1453
Table 1. Combustion energies of tetrazines 1–3*
Test
mo
ΔТ
Q
qa
qi
qN
qcot
–ΔU'B
Compound 1
1
2
3
4
0.100831
0.075659
0.074610
0.119840
2.13457
1.89702
1.96027
2.23241
1144.19
1016.86
1050,76
1196.64
757.13
739.84
776.39
760.49
0.524
0.524
0.524
0.524
4.42
2.07
2.04
4.49
6.74
6.07
7.12
6.04
3544.3
3546.9
3547.6
3547.2
–∆U'в = 3546.5 2.1 cal·g–1
Compound 2
1
2
3
4
5
0.076797
0.071023
0.079823
0.081317
0.081924
2.35093
2.33160
2.42102
2.40201
2.42271
1263.84
1253.44
1301.52
1291.30
1302.42
989.80
980.26
995.26
979.78
988.81
3.824
3.824
3.824
3.824
3.824
2.35
2.21
2.51
2.54
2.58
7.49
7.61
8.36
8.17
7.75
3650.9
3654.3
3652.6
3652.2
3655.4
–∆U'в = 3653.1 2.0 cal·g–1
Compound 3
1
2
3
4
5
0.075299
0.084248
0.081874
0.080778
0.081228
1.86283
2.02763
2.42706
2.38783
2.39929
989.42
1076.96
1304.76
1283.67
1289.83
707.43
761.76
997.54
980.09
984.21
0.524
0.524
0.524
0.524
0.524
2.62
2.95
2.86
2.82
2.84
6.58
7.37
7.69
8.21
8.35
3615.8
3612.6
3617.1
3615.2
3618.3
–∆U'в = 3615.8 2.5 cal·g–1
* The notation used: mо – weight of the sample of the test compound in vacuum, g; ΔT – corrected temperature rise in the calorimeter, degrees;
Q – the amount of heat measured in a test, cal; qa – heat of the combustion of the auxiliary compound benzoic acid, cal; qi – ignition energy, cal; qN − correction
for the formation of nitric acid, cal; qcot − heat generation from combustion of the cotton thread, cal; ΔU'B − combustion energy of a compound in the bomb,
cal·g−1.
The enthalpies of formation of tetrazines 1–3 were
calculated based on the enthalpies of combustion using
equations (4)–(6), respectively:
Table 2. Enthalpies of combustion and formation of
1,2,4,5-tetrazine derivatives 1–3
–ΔHo ,
ΔHo ,
с
f
ΔHo [C2H4N6](cr) = 2ΔHo [CO2](g) + 2ΔHo [H2O](l)
+
Compound
kcal·mol−1
kcal·mol−1
f
f
f
+ 3ΔHo [N2](g) – ΔHo ,
(4)
(5)
(6)
f
с
395.9 0.2
71.2 0.2
1
2
3
ΔHo [C2H6N8](cr) = 2ΔHo [CO2](g) + 3ΔHo [H2O](l)
+
f
f
f
+ 4ΔHo [N2](g) – ΔHo ,
f
с
517.3 0.3
493.7 0.3
124.3 0.3
108.9 0.3
ΔHo [C3H3N7](cr) = 3ΔHo [CO2](g) + 1.5ΔHo [H2O](l)
+
f
f
f
+ 3.5ΔHo [N2](g) – ΔHo ,
f
с
where ΔHo – the standard enthalpy of combustion of the
combustion of compound 2, confirming the accuracy of the
estimate.
с
corresponding compound, kcal·mol−1, and ΔHo – the
f
standard enthalpy of its formation, kcal·mol−1.
We have previously shown that the contribution of the
[1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine moiety, calculated
on the basis of the enthalpies of combustion of its 3-(3-R-
furazanylamino) derivatives, is –409.0 kcal·mol−1.6d The
contribution of this moiety, based on the enthalpy of
combustion of compound 3, is –409.6 kcal·mol−1, that is, it
is in good agreement with the value published previously.
The obtained data can be used to assess the enthalpy
characteristics of compounds containing 1,2,4,5-tetrazine
and [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine moieties.
In conclusion, it should be noted that recently the enthalpy
of formation of compound 3 was calculated using B3LYP
and B3P86 with the 6-311G** basis set.14 According to cal-
culations, this value was 148.16 and 146.21 kcal·mol−1,
respectively. As one can see, the calculated values are signi-
ficantly overestimated (compare with Table 2). Since the
enthalpy of formation of a compound is a key parameter in
the calculations of all important characteristics of energetic
materials, the use of incorrect starting data leads to fatal errors.
When calculating the standard enthalpies of formation of
the compounds of this study, we used the reference values
of the enthalpies of formation of combustion products:
ΔHo [CO2](g) = –94.051
0.031 and ΔHo [H2O](l)
=
f
f
= –68.315
0.009 kcal·mol−1.12 Table 2 compiles the
obtained thermochemical characteristics of the compounds
of this study.
Based on the obtained values of thermochemical para-
meters, the contribution of the 1,2,4,5-tetrazine moiety to
the enthalpy of combustion in the standard state was
estimated using the values of thermochemical contributions
to the enthalpy of combustion of amino and hydrazino
groups (–84.1 and –144.6 kcal·mol−1, respectively;
determined from benzene derivatives13). This contribution,
calculated from the thermochemical parameters of
compound 1, was –228.0 kcal·mol−1 (which corresponds to
–2.85 kcal·g−1) and differs only by 0.1 kcal from the value
obtained from the calculation from the enthalpy of
1451

Chemistry of Heterocyclic Compounds 2020, 56(11), 1449–1453
Experimental
3-(3,5-Dimethyl-1Н-pyrazol-1-yl)[1,2,4]triazolo[4,3-b]-
[1,2,4,5]tetrazine (7). Trifluoroacetic acid (5 ml, 0.067 mol)
was added dropwise to a suspension of compound 6 (4.12 g,
0.02 mol) in triethyl orthoformate (20 ml, 0.15 mol). In this
case, the mixture spontaneously heated up to 40°C, and a
solution was formed. After about half of the trifluoroacetic
acid has been added, a yellow amorphous precipitate began
to form. The reaction mixture was heated to 70°C and
allowed to cool. The formed precipitate was filtered off,
washed with aqueous i-PrOH, and dried. Yield 4.06 g
(94%), bright-yellow amorphous substance, mp 241–243°С
(mp 246–247°С,10 mp 248°С11). Spectral characteristics of
the product are identical to those described in the
literature.10 Found, %: С 44.50; Н 3.77; N 51.75. C8H8N8.
Calculated, %: С 44.44; Н 3.73; N 51.83.
IR spectra were registered on a Bruker Alpha
spectrometer in KBr pellets. 1H, 13C, and 14N NMR spectra
were acquired on a Bruker AМ-300 (300, 75, and 21 MHz,
respectively) in DMSO-d6. Chemical shifts of H and 13C
1
nuclei are given relative to TMS, for 14N nuclei – relative
to MeNO2. Mass spectra were recorded on a Finnigan
MATINCOS 50 mass spectrometer (direct sample
injection, EI ionization, 70 eV). Elemental analysis was
performed on a PerkinElmer Series II 2400 CHN-analyzer.
Melting points were determined on a Gallenkamp heating
bench and are uncorrected. Monitoring of the reaction
progress and assessment of the purity of synthesized
compounds were done by TLC on Sorbfil 60 F254 plates.
The starting compound 4 was obtained according to a
literature method.7
[1,2,4]Triazolo[4,3-b][1,2,4,5]tetrazin-6-amine (3).
Compound 7 (0.54 g, 2.5 mmol) was added to a mixture of
8% aqueous NH4OH (15 ml) and EtOH (20 ml). The
reaction mixture was heated under reflux for 2 h, after
which half of the solvent was evaporated. The residue was
extracted with CH2Cl2 (2×15 ml) to separate dimethyl-
pyrazole. i-PrOH (5 ml) was added to the aqueous phase.
The resulting mixture was left in the refrigerator overnight.
The next day, the formed precipitate was filtered off and air-
dried. The product was recrystallized from H2O, which,
according to the literature,10 led to the formation of the
monohydrate of the product with mp 217–218°С (H2O).
The substance was dried to constant weight in a drying
oven at 100–110°С (~24 h), which afforded the anhydrous
yellow amorphous product 3. Yield 0.2 g (58%), mp 186–
189°С (decomp.). IR spectrum, ν, cm–1: 3393, 3136, 3038,
2853, 1680, 1550, 1443, 1414, 1368, 1325, 1139, 1050,
970, 944, 872, 836, 761, 711, 696, 670. Mass spectrum, m/z
(Irel, %): 137 [M]+ 121, 98, 95, 86, 82, 77, 67, 57, 56, 55,
44. Found, %: С 26.31; Н 2.23; N 71.47. C3H3N7.
Calculated, %: С 26.28; Н 2.21; N 71.51. According to the
1H and 13C NMR spectra, the compound was identical to
that described in the literature.10
3,6-Bis(3,5-dimethyl-4-nitropyrazol-1-yl)-1,2,4,5-tetra-
zine (5). Concentrated HNO3 (d
1.5 g/cm3) (4 ml) was
added dropwise to a cooled (–10°С) trifluoroacetic anhyd-
ride (11.2 ml). The resulting solution was kept at –10°C
for 0.5 h, then cooled to –30°С, and anhydrous MeCN
(20 ml) was added dropwise. Tetrazine 4 (0.6 g, 2.2 mmol)
was added, and the mixture was allowed to warm up to
room temperature. The reaction mixture was stirred for an
additional 15 min at room temperature and poured onto ice.
The precipitate was filtered off, washed with H2O (3×15 ml)
and i-PrOH (5 ml), air-dried, and crystallized from МеСN.
Yield 0.78 g (98%), pink amorphous powder, mp 284–286°С.
IR spectrum, ν, cm–1: 1576, 1516, 1504, 1452, 1436, 1412,
1380, 1348, 1176, 1132, 1064, 1036, 996, 940, 848, 792,
1
764. H NMR spectrum, δ, ppm: 2.40 (12Н, br. s, 4CH3).
13C NMR spectrum, δ, ppm: 12.2; 13.8; 132.4; 143.5;
147.3; 152.3. 14N NMR spectrum, δ, ppm: –14.4 (NO2).
Mass spectrum, m/z (Irel, %): 360 [M]+ (19), 167 (28), 149
(47), 121 (100), 93 (67), 80 (53), 67 (82), 53 (61), 39 (72).
Found, %: С 40.08; Н 3.41; N 38.78. C12H12N10O4.
Calculated, %: С 40.00; Н 3.36; N 38.88.
3,6-Diamino-1,2,4,5-tetrazine (1). 33% Aqueous NH3
(30 ml) was added with stirring at room temperature to a
suspension of compound 5 (5 g, 0.014 mol) in glyme
(30 ml). A precipitate formed from the resulting solution
after about 1 h of stirring. The precipitate was filtered off,
washed with a CCl4–i-PrOH, 5:1 mixture, and dried in air.
Yield 1.9 g (97%), fine red-brown crystals, mp 300°С
(decomp.) (mp > 350°C15). Physicochemical and spectral
characteristics of the product are identical to those
described in the literature.16 Found, %: С 21.47; Н 3.65;
N 74.92. C2H4N6. Calculated, %: С 21.43; Н 3.60; N 74.97.
3,6-Dihydrazino-1,2,4,5-tetrazine (2). N2H4·H2O (0.5 g,
0.01 mol) was added dropwise at room temperature to a
vigorously stirred solution of compound 5 (1.8 g, 0.005 mol)
in glyme (20 ml), and after 5 min the resulting mixture was
cooled to 0°C. The precipitate was filtered off, washed with
a CCl4–i-PrOH, 5:1 mixture, and dried in air. Yield of
product 2 1.7 g (98%), red-brown solid, mp 160–162°С
(decomp.), identical in all respects to that described in the
literature.10 Found, %: С 16.97; Н 4.27; N 78.78. C2H6N8.
Calculated, %: С 16.90; Н 4.26; N 78.84.
Calorimetric measurements. The combustion energies
for the compounds of this study were determined on a
precision automatic combustion calorimeter with an
isothermal shell (designed by the Laboratory of
thermodynamics of energetic compounds of the Institute of
Chemical Physics of the Russian Academy of Sciences),
developed specifically for the study of energetic
materials.17 Samples of the studied compounds (usually
from 0.07 to 0.12 g) were weighed in a platinum crucible
and placed into the bomb of the calorimeter which was then
filled with oxygen. The initial oxygen pressure during
combustion of all compounds was about 3 MPa. Before the
experiment, distilled H2O (1 ml) was injected into the
bomb to create a saturated vapor pressure and dissolve
nitrogen oxides formed during combustion. A detailed
procedure for the preparation of the sample and the
combustion experiment has been described earlier.15
Supplementary information file containing information
on calorimetric measurements is available at the journal
website at http://link.springer.com/journal/10593.
1452

Chemistry of Heterocyclic Compounds 2020, 56(11), 1449–1453
Yin, H.; Chen, F.-X. Propellants, Explos., Pyrotech. 2019, 44,
N. V. Palysaeva and A. B. Sheremetev thank the Russian
Science Foundation (grant 20-13-00289) for their support.
Thermochemical studies were carried out by T. S. Kon'ko-
va, Yu. N. Matyushin, and E. A. Miroshnichenko within the
framework of the State assignment to N. N. Semenov
Federal Research Center for Chemical Physics, Russian
Academy of Sciences on topic 44.8 (0082-2014-0012).
1010. (j) Sinditskii, V. P.; Burzhava, A. V.; Usuntsinova, A. V.;
Egorshev, V. Yu.; Palysaeva, N. V.; Suponitsky, K. Yu.;
Ananiev, I. V.; Sheremetev, A. B. Combust. Flame 2020, 213,
343. (k) Wu, J.-T.; Xu, J.; Li, W.; Li, H.-B. Propellants,
Explos., Pyrotech. 2020, 45, 536. (l) Gao, H.; Zhang, Q.;
Shreeve, J. M. J. Mater. Chem.
A 2020, 8, 4193.
(m) O'Sullivan, O. T.; Zdilla, M. J. Chem. Rev. 2020, 120,
5682.
References
6. (a) Stinecipher, M. M. In 49th Calorimetry Conference; Santa
Fe, 1994. (b) Licht, H.-H.; Ritter, H. J. Energ. Mater. 1994,
12, 223. (c) Chavez, D. E.; Hiskey, M. A. J. Pyrotech. 1998, (7),
11. (d) Konkova, T. S.; Matyushin, Yu. N.; Miroshnichenko, E. A.;
Vorobev, A. V.; Palysaeva, N. V.; Sheremetev, A. B. Russ. J.
Phys. Chem. B 2020, 14, 69. [Khim. Fizika 2020, 39(1), 47.]
7. Coburn, M. D.; Buntain, G. A.; Harris, B. W.; Hiskey, M. A.;
Lee, K.-Y.; Ott, D. G. J. Heterocycl. Chem. 1991, 28, 2049.
8. Tolshchina, S. G.; Rusinov, G. L.; Charushin, V. N. Chem.
Heterocycl. Compd. 2013, 49, 66. [Khim. Geterotsikl. Soedin.
2013, 75.]
9. (a) Latosh, N. I.; Rusinov, G. L.; Ganebnykh, I. N.;
Chupakhin, O. N. Russ. J. Org. Chem. 1999, 35, 1363. [Zh. Org.
Khim. 1999, 35, 1392.] (b) Novák, Z.; Bostai, B.; Csékei, M.;
Lörincz, K.; Kotschy, A. Heterocycles 2003, 60, 2653.
10. Chavez, D. E.; Hiskey, M. A. J. Heterocycl. Chem. 1998, 35,
1329.
1. (a) Pepekin, V. I.; Lebedev, Yu. А. Dokl. Akad. Nauk SSSR ,
1977, 234, 1391. (b) Pepepkin, V. I.; Gubin, S. А. Khim.
Fizika 2003, 22(9), 72. (c) Viktorov, S. B.; Gubin, S. А.
Maklashova, I. V.; Pepekin, V. I. Khim. Fizika 2005, 24(12), 22.
(d) Pepekin, V. I. Dokl. Phys. Chem. 2007, 414, 159. [Dokl.
Akad. Nauk 2007, 414, 781.] (e) Pepekin, V. I.; Gubin, S. A.
Comb. Explos. Shock Waves 2007, 43, 84. [Fizika goreniya i
vzryva 2007, 43(1), 99.] (f) Pepekin, V. I. Russ. J. Phys.
Chem. B 2010, 4, 954. [Khim. Fizika 2010, 29(12), 8.]
(g) Bogdanova, Yu. A.; Gubin, S. A.; Korsunskii, B. L.;
Pepekin, V. I. Comb. Explos. Shock Waves 2009, 45, 738.
[Fizika goreniya i vzryva 2009, 45(6), 115.] (h) Pepekin, V. I.
Russ. J. Phys. Chem. B 2011, 5, 41. [Khim. Fizika 2011, 30
(1), 20].
2. Fizika vzryva (Explosion Physics [in Russian]); Orlenko, L. P.,
Ed.; Moscow: Fizmatlit, Vol. 1, 2002.
11. Rusinov, G. L.; Ganebnykh, I. N.; Chupakin, O. N. Russ. J.
Org. Chem. 1999, 35, 1350. [Zh. Org. Khim. 1999, 35, 1379.]
12. Cox, J. D.; Wagman, D. D.; Medvedev, V. A. CODATA Key
Values for Thermodynamics; Hemisphere Publishing Corp.:
New York, 1989.
13. (a) Pedley, J. B. Thermochemical Data and Structures of
Organic Compounds; Thermodynamic Research Center:
College Station, 1994, Vol. 1, p. 200. (b) Walters, R. N. Fire
Mater. 2002, 26, 131. (c) Sagadeev, E. V.; Gimadeev, A. A.;
Barabanov, V. P. Theor. Found. Chem. Eng. 2009, 43, 108.
[Teor. osnovy khim. tekhnologii 2009, 43, 114.]
14. Wei, T.; Zhu, W.; Zhang, J.; Xiao, H. J. Hazard. Mater. 2010,
179, 581.
15. Kon'kova, T. S.; Matyushin, Yu. N.; Miroshnichenko, Е. А.;
Vorob'ev, A. B. Russ. Chem. Bull., Int. Ed. 2009, 58, 2020.
[Izv. Akad. Nauk, Ser. Khim. 2009, 1958.]
16. (a) Coburn, M. D.; Ott, D. G. J. Heterocycl. Chem. 1990, 27,
1941. (b) Glidewell, C.; Lightfoot, P.; Royles, B. J. L.;
Smith, D. M. J. Chem. Soc., Perkin Trans. 2 1997, 1167.
17. Inozemtsev, Ya. О.; Vorob'ev, А. B.; Inozemtsev, А. V.
Matyushin, Yu. N. Gorenie i vzryv 2014, 7, 260.
3. Pepekin, V. I.; Korsunskii, B. L.; Denisaev, A. A. Comb.
Explos. Shock Waves 2008, 44, 586. [Fizika goreniya i vzryva
2008, 44(5), 101.]
4. Green Energetic Materials; Brinck, T., Ed.; Wiley:
Chichester, 2014.
5. (a) Keshavarz, M. H.; Abadi, Y. H.; Esmaeilpour, K.; Damiri, S.;
Oftadeh, M. Chem. Heterocycl. Compd. 2017, 53, 797. [Khim.
Geterotsikl. Soedin. 2017, 53, 797.] (b) Rudakov, G. F.;
Moiseenko, Y. A.; Spesivtseva, N. А. Chem. Heterocycl.
Compd. 2017, 53, 802. [Khim. Geterotsikl. Soedin. 2017, 53,
802.] (c) Sinditskii, V. P.; Smirnov, S. P.; Egorshev, V. Yu.;
Chernyi, A. N.; Shkineva, T. K.; Palysaeva, N. V.;
Suponitsky, K. Yu.; Dalinger, I. L. Thermochim. Acta 2017, 651,
83. (d) Wang, G.; Lu, T.; Fan, G.; Li, C.; Yin, H.; Chen, F.-X.
Chem.–Asian. J. 2018, 13, 3718. (e) Chen, D.; Yang, H.; Yi, Z.;
Xiong, H.; Zhang, L.; Zhu, S.; Cheng. G. Angew. Chem., Int.
Ed. 2018, 57, 2081. (f) Shyder, C. J.; Wells, L. A.; Chavez, D. E.;
Imler, G. H.; Parrish, D. A. Chem. Commun. 2019, 2461.
(g) Zhu, W.; Ye, Z.; Dong, Z. New J. Chem. 2019, 43, 16300.
(h) Ren, J.; Zhang, T.; Li, Z.; Wang, L.; Zhang, T.
Thermochim. Acta 2019, 682, 178391. (i) Wang, G.; Fu, Z.;
1453