Synthesis and structural study of 4,6-diazido-2-(2,2,2-trinitroethylamino)-1,3,5-triazine

Article abstract of DOI:10.1007/s11172-016-1608-4

A method for synthesis of 2-(2,2,2-trinitroethylamino)-4,6-diazido-1,3,5-triazine from 2-amino-4,6-diazido-1,3,5-triazine was elaborated. The molecular and crystal structures of this compound were studied using X-ray diffraction analysis.

Full text of DOI:10.1007/s11172-016-1608-4

Russian Chemical Bulletin, International Edition, Vol. 65, No. 10, pp. 2469—2474, October, 2016
2469
Synthesis and structural study
of 4,6ꢀdiazidoꢀ2ꢀ(2,2,2ꢀtrinitroethylamino)ꢀ1,3,5ꢀtriazine*
A. V. Shastin, A. G. Korepin, Z. G. Aliev, D. V. Korchagin, N. M. Glushakova, V. S. Malygina,
V. P. Kosilko, V. P. Lodygina, G. V. Lagodzinskaya, and S. M. Aldoshin
Institute of Problems of Chemical Physics, Russian Academy of Sciences,
1
prosp. Akad. Semenova, 142432 Chernogolovka, Moscow Region, Russian Federation.
Fax: +7 (496) 522 3507. Eꢀmail: shastin@icp.ac.ru
A method for synthesis of 2ꢀ(2,2,2ꢀtrinitroethylamino)ꢀ4,6ꢀdiazidoꢀ1,3,5ꢀtriazine from
ꢀaminoꢀ4,6ꢀdiazidoꢀ1,3,5ꢀtriazine was elaborated. The molecular and crystal structures of this
2
compound were studied using Xꢀray diffraction analysis.
Key words: 2ꢀaminoꢀ4,6ꢀdiazidoꢀ1,3,5ꢀtriazine, 2ꢀ(2,2,2ꢀtrinitroethylamino)ꢀ4,6ꢀdiazidoꢀ
1
,3,5ꢀtriazine, trinitroethyl group, quantum chemistry, Xꢀray diffraction analysis, synthesis.
Interest in compounds containing residues of polyaza
heterocycles and polynitromethyl (trinitromethyl, fluoroꢀ
dinitromethyl, dinitromethyl, and trinitroethyl) groups is
Scheme 1
caused by the possibility of their use in powerꢀconsuming
compositions of various design.1
—22
In the case of the
1
,3,5ꢀtriazine derivatives, several compounds containing
23—26
trinitromethyl and trinitroethyl groups were described.
This work is devoted to the development of a method
for synthesis and study of the properties of 4,6ꢀdiazidoꢀ
2
ꢀ(2,2,2ꢀtrinitroethyl)aminoꢀ1,3,5ꢀtriazine (1). We inꢀ
tended to carry out the Nꢀtrinitroethylation of 2ꢀaminoꢀ
,6ꢀdiazidoꢀ1,3,5ꢀtriazine (2) to prepare this compound.
Several methods for the synthesis of compound 2 were
4
described.2
7—30
The twoꢀstep method including the prepꢀ
aration of 2ꢀaminoꢀ4,6ꢀdichloroꢀ1,3,5ꢀtriazine (3) from
cyanuric chloride (4) followed by chlorine substitution
under the action of sodium azide in aqueous ethanol
Reagents and conditions: i. NH3—acetone, 0—5 °С;
ii. NaN —H O, EtOH.
(
Scheme 1) seems to be most convenient.30 The yield of
3
2
compound 2 within two steps was 65% based on the
starting cyanuric chloride.
solutions16,19 were unsuccessful because of, most likely,
low solubility of aminodiazidotriazine 2 in these solvents.
Only dimethyl sulfoxide dissolves well compound 2 of the
tested organic solvents (dimethyl sulfoxide, acetone, diꢀ
oxane, methanol), while other solvents dissolve this comꢀ
pound rather restrictedly. Nevertheless, compound 1 was
also obtained in acetone and dioxane, but the yields were
at a level of several percents. We found that compound 1
cannot be synthesized in any of the tested solvents listed
above by the simple interaction with trinitroethanol or
Several method for trinitroethylation of heterocyclic
1
,4,6,8,16,18,19,25,26
amines are known.
standard trinitroethylation methods1
However, the use of
,4,6,8,16,19,25,26
gave no
positive results in our case. Only the Nꢀtrinitroethylation
of aminodiazidotriazine 2 in a dimethyl sulfoxide medium
(
dimethyl sulfoxide was applied earlier as the solvent for
1
8
trinitroethylation of some aminofuroxans ) and catalysis
with alkali at the step of formation of hydroxymethylamine 5
were successful (Scheme 2). Our attempts to obtain comꢀ
with formaldehyde and trinitromethane, as it was made
pound 1 in an aqueous medium similarly to the previous
25,26
earlier,
or by the addition of hydrochloric acid to
syntheses1
,4,6,8,25,26
in methanol and hydrochloric acid
16,19
these reagents.
The necessary condition for the forꢀ
mation of compound 1 is the use of catalytic amounts of
sodium hydroxide. It is most likely that the amino group in
triazine 2 is so lowly basic than its activation with an alkaline
*
To the 60th anniversary of the Institute of Problems of Chemical
Physics, Russian Academy of Sciences.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2469—2474, October, 2016.
066ꢀ5285/16/6510ꢀ2469 © 2016 Springer Science+Business Media, Inc.
1

2
470
Russ.Chem.Bull., Int.Ed., Vol. 65, No. 10, October, 2016
Shastin et al.
O(6)
agent is needed for the formation of intermediate hyꢀ
droxymethylamine 5. The yields of 1 in the primary exꢀ
periments using dimethyl sulfoxide and sodium hydroxꢀ
ide were low and noticeably changed with a change in the
ratio of all components of the reaction mixture. The optiꢀ
mization of the component ratio resulted in the yield of
compound 1 not lower than 36% (see Experimental).
O(4)
O(3)
O(1)
O(5)
N(13)
N(12)
C(5)
N(5) N(6)
N(7)
N(1)
N(11)
N(4)
O(2)
N(2)
C(4)
C(1)
C(3)
N(10)
Scheme 2
N(3)
N(9)
N(8)
Fig. 1. Structure of molecule 1 with 50% ellipsoids of thermal
vibrations.
dimeric associates multiplied by the 2ꢀfold screw axis are
bound by hydrogen bonds C(4)—H(4а)...O(3) with a
length of 3.107(2) Å and form an infinite layer in the (101)
direction of the cell (Fig. 2).
The Xꢀray study revealed certain specific features in
the structure of this compound. A molecule of diazide 1
is shown to crystallize in the form of Z,Zꢀconformer as in
Reagents and conditions: i. CH O—NaOH, DMSO;
2
ii. CH(NO ) , H SO .
2
3
2
4
Diazide 1 was nitrated (by a sulfuric—acidic mixture,
35
the case of 6ꢀaminoꢀ2,4ꢀdiazidoꢀ1,3,5ꢀtriazine 2. The
1
00% nitric acid, an HNO —(CF CO) O system, and an
3
3
2
quantum chemical calculation data indicate that in the
gas phase of the Z,Zꢀconformer is not the most stable
conformer, but its total energy is fairly close to that for the
E,Zꢀconformer (Fig. 3). The differences in these conformꢀ
ers in energy are so small that the influence of the crystal
packing can result in the stabilization of the Z,Zꢀconꢀ
former as in crystals of both 6ꢀaminoꢀ2,4ꢀdiazidoꢀ1,3,5ꢀ
triazine 2 and compound 1. Unlike 6ꢀaminoꢀ2,4ꢀdiazidoꢀ
3
0—34
HNO —Ac O—AcCl system)
to obtain the correꢀ
3
2
sponding nitramine 6. When a sulfuric—nitric mixture,
00% nitric acid, and a mixture of nitric acid with trifluoꢀ
1
roacetic anhydride were used, compound 1 recovered from
the reaction unchanged in a yield of 80—90%. About 50%
of compound 1 recovered when an HNO —Ac O—AcCl
3
2
system was used, and no Nꢀnitration product was found in
the reaction mixture (Scheme 3).
1
,3,5ꢀtriazine 2, whose E,Zꢀ and Z,Eꢀconformers are
equivalent in energy, the Z,Eꢀconformer of diazide 1 is
–
1
energetically less favorable (by ~0.26 kcal mol ) relative
to the most stable E,Zꢀconformer, which can be a result of
the electronic and steric influence of the trinitroethyl subꢀ
stituent. In the both cases considered, the E,Eꢀconformer
is least stable in the gas phase.
Scheme 3
Note that the compound synthesized by us is the first
example of the 1,3,5ꢀtriazine derivative containing a comꢀ
bination of trinitroethylamino and azido groups. The enꢀ
thalpy of formation of this compound in the condensed
phase calculated (by analogy to Ref. 36) using the
3
7
–1
The structure of 4,6ꢀdiazidoꢀ2ꢀ(2,2,2ꢀtrinitroethylꢀ
amino)ꢀ1,3,5ꢀtriazine (1) was proved by an array of phyꢀ
sicochemical methods and confirmed by elemental analyꢀ
sis data. The Xꢀray diffraction study performed unamꢀ
biguously proved the structure of the obtained substance
CBSꢀ4M method is 169.2 kcal mol . The tentative paꢀ
rameters of the explosive transformation and sensitivity to
impact calculated for compound 1 using the methods deꢀ
38,39
scribed
are given in Table 1. The data for 2,4ꢀdiazidoꢀ
6ꢀtrinitromethylꢀ1,3,5ꢀtriazine (7), 2ꢀnitraminoꢀ4,6ꢀdiꢀ
azidoꢀ1,3,5ꢀtriazine (8), and octogen (9) are presented in
Table 1 for comparison. The values of density and enꢀ
thalpy of formation for compounds 7, 8, and 9 were taken
from published works.
cate that, in spite of the high enthalpy of formation, the
(Fig. 1).
Compound 1 exists in crystal as centrosymmetric
dimeric associates formed by intermolecular hydrogen
bonds N(4)—H(4)...N(3) with the following parameters:
r(H(4)...N(3)) 2.18(2) Å and r(N(4)...N(3)) = 3.001(2) Å,
and the angle at the hydrogen atom is 163.6(2)°. The
2
1,30,40,41
The data in Table 1 indiꢀ
synthesized compound is inferior to substances 7, 8, and 9

4,6ꢀDiazidoꢀ2ꢀ(2,2,2ꢀtrinitroethylamino)ꢀ1,3,5ꢀtriazine Russ.Chem.Bull., Int.Ed., Vol. 65, No. 10, October, 2016
2471
a
H(4a)
O(3)
N(4)
N(3)
c
0
Fig. 2. Projection of structure 1 along the axis of crystal monoclinicity.
a
b
c
d
ZZ (0.04)
EZ (0.00)
ZE (0.26)
EE (0.75)
e
f
g
N
C
O
H
ZZ (0.05)
EZ и ZE (0.00)
EE (0.43)
Fig. 3. Optimized geometries and the relative energies (kcal mol–1) of the most stable conformers of diazidotriazines 1 (a—d) and 2 (e—g).

2
472
Russ.Chem.Bull., Int.Ed., Vol. 65, No. 10, October, 2016
Shastin et al.
Table 1. Comparative characteristics of compounds 1, 7, 8, and 9
Comꢀ
pound
Empirical
formula
OB
(%)
ρ
ΔH°f
/kcal mol
θmax
/kcal kg
vd
/m s
pcr
/kbar
–
3
–1
–1
–1
/g cm
1
7
8
9
C H N O
–25.8
–10.3
–32.3
–21.6
1.743
1.826
1.849
1.91
169.2
191.2
176.0
20.08
1417
1516
1365
1626
7870
8110
8080
8960
9.7
8.5
12.5
6.4
5
3
13
6
2
C N O
6
4
12
C H N O
3
1
11
C H N O
8
4
8
8
Note. OB is oxygen balance, ρ is density, ΔHfo is the enthalpy of formation (condensed phase), θmax is the
maximum heat of explosion, v is the detonation rate, and p is the critical pressure.
d
cr
in the calculated detonation rate. This is related, most
likely, to a comparatively low density of a single crystal of
compound 1.
The presence of at least four reaction centers in comꢀ
pound 1 makes it possible to use this compound for the
design of new powerꢀconsuming substances by the modiꢀ
fication of the trinitromethyl group, amino group, or aziꢀ
do groups. The preliminary data on the thermal stability
hydrogen atoms) leastꢀsquares refinement was performed using the
4
5
SHELXLꢀ973 program and completed at R = 0.0393, wR =
1
2
0
0
.0970 for 2863 reflections with I > 2σ(I) and R = 0.0503, wR =
.1056 for all 3470 reflections; GOOF = 1.016. The number of
1 2
refined parameters was 231. The maximum electron density in the
difference electron density synthesis was 0.241 е Å–3. The CIF file
containing the full information on the studied structure was deposꢀ
ited with the Cambridge Crystallographic Data Centre (CIF file
1450436) and can be obtained free of charge at
www.ccdc.cam.ac.uk/data_request/cif. The data on the Xꢀray
diffraction experiment, bond lengths, and angles are presented
in Tables 2 and 3.
2ꢀAminoꢀ4,6ꢀdiazidoꢀ1,3,5ꢀtriazine (2) was synthesized usꢀ
ing a described procedure.30 The yield within two steps was 65%
based on cyanuric chloride. The substance decomposed without
melting at temperatures higher than 220 °C. Published data:
(
DSCꢀTG) indicate that compound 1 is not inferior in
thermal stability (decomposition onset/exoꢀpeak, 172.6/
1
90.8 °C) to the trinitroethyl derivatives of the fiveꢀmemꢀ
1
,4,6,8,16,17,19
bered heterocycles.
However, for refinement
this compound needs to be studied in more detail, since
the DSCꢀTG data can provide an incomplete knowledge
4
2
about the thermal stability of the substance.
decomposition higher than 200 °C (see Ref. 27), m.p. 260 °C
1
(
see Ref. 29). IR ν/cm– : 3332, 3201, 1666, 657 (NН ); 2151,
2
Experimental
1210 (N3); 1583, 1560, 1529, 1367, 805 (triazine, cycle).
IR spectra were recorded on an ALPHAꢀBruker FTꢀIR
spectrometer in KBr pellets. 1H, C, and N NMR spectra
were obtained on a Bruker Avance III 500 instrument (500, 126,
and 36 MHz, respectively) in a DMSOꢀd —CCl (75 : 25 vol/
13
14
Table 2. Crystallographic data and parameters of Xꢀray
structural experiment for compound 1
6
4
1
13
vol) mixture. The Н and C chemical shifts are presented relaꢀ
14
Parameter
Value
tive to SiMe , and those for N are relative to nitromethane.
4
Melting points were determined on a Boetius heating stage with
a heating rate of 4 deg min–1 near the melting point. The
DSCꢀTG experiment was carried out using a NETZSCH STA
Formula
Molecular weight
Space group
a/Å
b/Å
C H N O
6
341.20
P2(1)/n
11.0583(5)
9.5311(4)
12.8989(6)
90.00
106.995(5)
90.00
1300.15(10)
4
1.743
0.157
2.88—29.07
5
3
13
4
09C Luxx simultaneous thermal analyzer in an argon flow
–
1
–1
(
40 mL min ) with a heating rate of 5 deg min in a range of
3
0—350 °C.
c/Å
Quantum chemical calculations were performed in terms of
α/deg
β/deg
γ/deg
V/Å3
Z
the density functional theory in the B3LYP/6ꢀ311G(d,p) apꢀ
4
3
proximation using the Gaussian 09 program.
Single crystals of compound 1 were obtained by crystallizaꢀ
tion from CCl . The Xꢀray diffraction experiment was carried
4
out on an XCalibur CCD diffractometer with an EOS detector.
Data collection and processing, as well as determination and
refinement of unit cell parameters, were performed using the
CrysAlis PRO program44 on molybdenum radiation at 150.0(1) K
in an angle range of 2.88—29.07°. The total number of measured
reflections was 6605 of which 3470 reflections were independent
–
3
dcalc/g cm
μ/mm–
1
Scan range (θ/deg)
Number of reflections
measured (Rint
with I > 2σ(I)
Number of refined parameters
GOOF
)
6605
2863
231
1.016
0.0393
0.0970
(
Rint = 0.0164). The structure was solved by a direct method
using the program followed by a series of calculations of the
electron density maps. Hydrogen atoms were objectively localꢀ
ized from difference electron density syntheses and refined in
the isotropic approximation. The fullꢀmatrix anisotropic (for nonꢀ
R (I > 2σ(I))
l
wR2

4,6ꢀDiazidoꢀ2ꢀ(2,2,2ꢀtrinitroethylamino)ꢀ1,3,5ꢀtriazine Russ.Chem.Bull., Int.Ed., Vol. 65, No. 10, October, 2016
2473
Table 3. Bond lengths (d) and bond angles (ω) in structure 1
Bond d/Å Bond d/Å
Angle
ω/deg
Angle
ω/deg
C(1)—N(1) 1.3401(16)
C(1)—N(3) 1.3503(16)
C(1)—N(4) 1.3514(16)
C(2)—N(1) 1.3268(16)
C(2)—N(2) 1.3355(16)
C(2)—N(5) 1.3962(16)
C(3)—N(3) 1.3271(16)
C(3)—N(2) 1.3327(16)
C(3)—N(8) 1.3969(16)
C(4)—N(4) 1.4308(16)
C(4)—C(5) 1.5366(17)
C(5)—N(12) 1.5169(18)
C(5)—N(11) 1.5199(17)
C(5)—N(13) 1.5221(18)
N(1)—C(1)—N(3)
N(1)—C(1)—N(4)
N(3)—C(1)—N(4)
N(1)—C(2)—N(2)
N(1)—C(2)—N(5)
N(2)—C(2)—N(5)
N(3)—C(3)—N(2)
N(3)—C(3)—N(8)
N(2)—C(3)—N(8)
N(4)—C(4)—C(5)
125.43(11) N(11)—C(5)—N(13) 106.29(11)
118.83(11) N(12)—C(5)—C(4)
115.73(11) N(11)—C(5)—C(4)
127.33(11) N(13)—C(5)—C(4)
113.53(11) C(2)—N(1)—C(1)
119.14(11) C(3)—N(2)—C(2)
127.46(11) C(3)—N(3)—C(1)
113.28(11) C(1)—N(4)—C(4)
119.25(11) N(6)—N(5)—C(2)
112.42(11) N(7)—N(6)—N(5)
112.26(10)
113.42(11)
110.15(11)
113.64(11)
112.52(11)
113.28(11)
122.97(11)
113.41(11)
170.91(14)
112.67(11)
N(5)—N(6)
N(6)—N(7)
N(8)—N(9)
1.2664(16)
1.1144(17)
1.2671(16)
N(9)—N(10) 1.1112(16)
N(11)—O(2) 1.2102(17)
N(11)—O(1) 1.2177(16)
N(12)—O(3) 1.2130(15)
N(12)—O(4) 1.2150(16)
N(13)—O(5) 1.2142(19)
N(13)—O(6) 1.2143(18)
N(12)—C(5)—N(11) 105.86(10) N(9)—N(8)—C(3)
N(12)—C(5)—N(13) 108.55(11)
4
,6ꢀDiazidoꢀ2ꢀ(2,2,2ꢀtrinitroethylamino)ꢀ1,3,5ꢀtriazine (1).
4. P. Yin, J. Zhang, C. He, D. A. Parrish, J. M. Shreeve,
J. Mater. Chem. A, 2014, 2, 3200.
Compound 2 (0.9 g, 0.0051 mol) was added to a mixture of 25%
aqueous formalin (2.5 g, 0.021 mol) and dimethyl sulfoxide
5. V. Thottempudi, H. X. Gao, J. M. Shreeve, J. Am. Chem. Soc.,
2011, 133, 6464.
(15 mL), the mixture was stirred at room temperature for 30 min, and
a solution of NaOH (0.04 g, 0.001 mol) in Н О (5 mL) was added.
The obtained suspension was stirred to the complete dissolution of
6. Y. X. Tang, H. W. Yang, J. X. Hu, C. X. Lu, G. B. Cheng,
J. Energ. Mater., 2015, 33, 145.
2
the solid phase (1 day). Then a solution of H SO4 (50 mg,
7. Y. X. Tang, C. L. He, H. X. Gao, J. M. Shreeve, J. Mater.
Chem. A, 2015, 3, 15576.
8. Q. H. Zhang, J. H. Zhang, D. A. Parrish, J. M. Shreeve,
Chem. Eur. J., 2013, 19, 11000.
2
0
.0005 mol) in water (2.5 mL) was added dropwise with cooling in a
water bath to 14—16 °C. In 20—30 min, a solution of trinitromethane
10 g, 0.066 mol) in water (33 mL) was added at room temperature.
(
The reaction mixture was kept at room temperature for 3 days. The
precipitate formed was filtered off, several times washed with water,
and dried in air to a constant weight. 4,6ꢀDiazidoꢀ2ꢀ(2,2,2ꢀtriniꢀ
troethylamino)ꢀ1,3,5ꢀtriazine was obtained in a yield of 0.62 g (36%)
as colorless crystals with m.p. 113—114 °C. After recrystallization
9. R. Haiges, K. O. Christe, Inorg. Chem., 2013, 52, 7249.
10. O. A. Luk´yanov, G. V. Pokhvisneva, T. V. Ternikova, Russ.
Chem. Bull. (Int. Ed.), 2015, 64, 137 [Izv. Akad. Nauk, Ser.
Khim., 2015, 137].
11. V. V. Parakhin, O. A. Luk´yanov, Russ. Chem. Bull. (Int.
Ed.), 2013, 62, 2007 [Izv. Akad. Nauk, Ser. Khim., 2013,
2007].
12. O. A. Luk´yanov, G. V. Pokhvisneva, T. V. Ternikova, Russ.
Chem. Bull. (Int. Ed.), 2012, 61, 1783 [Izv. Akad. Nauk, Ser.
Khim., 2012, 1767].
13. O. A. Luk´yanov, V. V. Parakhin, Russ. Chem. Bull. (Int.
Ed.), 2012, 61, 1582 [Izv. Akad. Nauk, Ser. Khim., 2012,
1566].
–1
from CCl m.p. 113—114 °C. IR, ν/cm : 3263, 3131 (NН); 2145,
4
1
1
212 (N ); 1614, 1586, 1564, 1362, 803 sh (triazine, cycle); 1448,
3
1
336, 813 (NO ). H NMR (DMSOꢀd —CCl ), δ: 5.38 (d, 2 H,
2
6
4
13
CH , J = 6.5 Hz); 9.36 (t, 1 H, NH, J = 6.5 Hz). C NMR
2
(
1
DMSOꢀd —CCl ), δ: 170.54, 170.20, 168.15 (CN triazine);
6 4
14
25.07 [C(NO ) ]; 44.70 (CH ). N NMR (DMSOꢀd —CCl ),
2
3
2
6
4
δ: –33.1 [C(NO ) ], –140.0 (N , broad signal). Found (%):
2
3
3
C, 17.61; H, 0.84; N, 52.91; O, 28.13. C H N O . Calcuꢀ
5
3
13
6
lated (%): C, 17.60; H, 0.89; N, 53.37; O, 28.14.
14. O. A. Luk´yanov, G. V. Pokhvisneva, T. V. Ternikova, N. I.
Shlykova, Russ. Chem. Bull. (Int. Ed.), 2012, 61, 360 [Izv.
Akad. Nauk, Ser. Khim., 2012, 358].
15. O. A. Luk´yanov, G. V. Pokhvisneva, T. V. Ternikova, N. I.
Shlykova, M. E. Shagaeva, Russ. Chem. Bull. (Int. Ed.), 2011,
This work was financially supported by the Ministry of
Education and Science of the Russian Federation in terms
of the Agreement No. 14.613.21.0043 of 10.11.2015
6
0, 1703 [Izv. Akad. Nauk, Ser. Khim., 2011, 1678].
(
unique identifier RFMEFI61315X0043).
1
1
6. Q. Yu, Z. Wang, B. Wu, H. Yang, X. Ju, C. Lu, G. Cheng,
J. Mater. Chem. A, 2015, 3, 8156.
7. A. B. Sheremetev, N. S. Aleksandrova, N. V. Palysaeva, M. I.
Struchkova, V. A. Tartakovsky, K. Yu. Suponitsky, Chem. Eur.
J., 2013, 19, 12446.
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Received February 4, 2016;
in revised form June 7, 2016