CN115448879B - Polynitro nitrogen-rich energy-containing compound and preparation method thereof - Google Patents
Polynitro nitrogen-rich energy-containing compound and preparation method thereof Download PDFInfo
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- CN115448879B CN115448879B CN202210992730.9A CN202210992730A CN115448879B CN 115448879 B CN115448879 B CN 115448879B CN 202210992730 A CN202210992730 A CN 202210992730A CN 115448879 B CN115448879 B CN 115448879B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 64
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 229910052757 nitrogen Inorganic materials 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims description 9
- AXIFLJXPRZLOFM-UHFFFAOYSA-N 5-methyl-3,4-dinitro-1h-pyrazole Chemical compound CC=1NN=C([N+]([O-])=O)C=1[N+]([O-])=O AXIFLJXPRZLOFM-UHFFFAOYSA-N 0.000 claims abstract description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 239000000463 material Substances 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 12
- CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 claims abstract description 8
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 7
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 6
- ASURMMBYYOJOTQ-UHFFFAOYSA-N 5-methyl-3-nitro-1h-pyrazole Chemical compound CC1=CC([N+]([O-])=O)=NN1 ASURMMBYYOJOTQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000002360 explosive Substances 0.000 claims abstract description 3
- 230000001546 nitrifying effect Effects 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 238000006396 nitration reaction Methods 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000005457 ice water Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 2
- 238000004176 ammonification Methods 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 230000000977 initiatory effect Effects 0.000 abstract description 2
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 238000005474 detonation Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000001291 vacuum drying Methods 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- -1 detonation velocity Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B25/00—Compositions containing a nitrated organic compound
- C06B25/34—Compositions containing a nitrated organic compound the compound being a nitrated acyclic, alicyclic or heterocyclic amine
Abstract
The invention provides a polynitro nitrogen-rich energetic compound, which is a 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound with a structural formula shown as a formula I:the method comprises the steps of nitrifying 5-methyl-3-nitropyrazole under the action of fuming sulfuric acid and concentrated nitric acid, carrying out ammonification reaction on the obtained product and THA, and then adding tert-butyl hypochlorite or a mixture of sodium dichloroisocyanurate and acetic acid to react to obtain the 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound. The energy-containing compound with higher nitrogen content and higher energy is prepared as a novel nitrogen-rich energy-containing material to be applied to the green high-energy high-temperature-resistant initiating explosive; the synthesis steps are short, and the environment is not polluted.
Description
Technical Field
The invention belongs to the technical field of preparation of energetic material materials, and particularly relates to a polynitro nitrogen-rich energetic compound and a preparation method thereof.
Background
Energetic materials are one of the indispensable materials for weapon systems, and there has been a trend to synthesize environmentally friendly compounds. The combustion products of nitrogen-rich compounds are mainly dinitrogen compounds and are therefore of increasing interest in the field of energetic materials. However, polynitronitrogen-rich compounds, while having good density and detonation properties, are generally less stable, limiting their further use. How to further improve the stability of energetic materials while increasing the nitrogen content of the energetic materials is now the focus of research.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides the polynitro nitrogen-rich energy-containing compound and the preparation method thereof, wherein the nitrogen content of the energy-containing material is improved by introducing an azo bridge, and simultaneously, the heat stability of the energy-containing material is further improved by introducing a methyl group, so that the technical problem of storage of the nitrogen-rich compound is solved, and the safety of the energy-containing material is comprehensively improved.
The invention solves the technical problems by adopting the following technical scheme:
the first aim of the invention is to provide a polynitro nitrogen-rich energy-containing compound which is a 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energy-containing compound with a structural formula shown as a formula I:
the second object of the present invention is to provide a method for preparing a polynitronitrogen-rich energetic compound, comprising the steps of:
1) Nitrifying 5-methyl-3-nitropyrazole under the action of concentrated sulfuric acid and fuming nitric acid and carrying out ammoniation reaction with THA to obtain a compound shown in a formula II;
2) Dissolving a compound of the formula II in acetonitrile, after the compound is completely dissolved, adding tert-butyl hypochlorite or a mixture of sodium dichloroisocyanurate and acetic acid under a low temperature condition, adding a saturated sodium carbonate solution to adjust the pH to be neutral after the reaction is finished, extracting with ethyl acetate, and vacuum drying to obtain the 1,1 '(1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound, wherein the 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound is a polynitronitrogen-rich energetic compound;
the structural formula of the compound of the formula II is as follows:
further, in the step 1), 98% by mass of concentrated sulfuric acid is added.
Further, the volume ratio of the concentrated sulfuric acid to fuming nitric acid is 2:1.
Further, the solution obtained after the nitration reaction in the step 1) is added into 20-50 mL of ice water, and then extracted by diethyl ether/ethyl acetate.
Further, in the step 1), after the nitration reaction and the extraction, an equivalent amount of DBU is added, and then THA is added for the ammonification reaction.
Further, the ratio of the compound of formula II to t-butyl hypochlorite in step 2) is 1mmol:1.5mmol.
Further, the ratio of the compound of formula II to sodium dichloroisocyanurate, acetic acid in step 2) is 1mmol:1mmol:0.5ml.
Further, the low-temperature reaction condition of the compound of the formula II in the step 2) and the tert-butyl hypochlorite is-20 ℃ for 12 hours.
Further, the low temperature reaction condition of the compound of the formula II in the step 2) and the mixture of sodium dichloroisocyanurate and acetic acid is 0 ℃ for 12 hours.
The third object of the present invention is to provide the use of a 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound as a nitrogen-rich energetic material.
Furthermore, the energy-containing compound of 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) is used as a nitrogen-rich energy-containing material to be applied to the application of the green high-energy high-temperature-resistant initiating explosive.
Compared with the prior art, the invention has the beneficial technical effects that:
according to the invention, from available commercial raw materials, the nitro is introduced into an energetic complex system as an energy group, so that the oxygen balance level of molecules is improved, and meanwhile, an azo bridge is introduced, so that the nitrogen content of the molecules is improved, and the energy performance of the energetic material is improved. Finally, methyl is introduced as a stabilizing group to improve the thermal stability of the molecule. The preparation method is simple, and is environment-friendly and pollution-free. The nitrogen content of the 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound of the present invention was 37.84%.
The foregoing description is only an overview of the present invention, and is intended to be implemented in accordance with the teachings of the present invention in order that the same may be more clearly understood and to make the same and other objects, features and advantages of the present invention more readily apparent.
Drawings
FIG. 1 is a diagram showing the crystal structure of the energetic compound 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) prepared in example 1 of the present invention.
FIG. 2 is a nuclear magnetic resonance image of the 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound prepared in example 1 of the present invention.
Detailed Description
The technical scheme of the invention is further described in detail below with reference to the attached drawings and specific embodiments. It is to be understood that the following examples are illustrative only and are not to be construed as limiting the scope of the invention. All techniques implemented based on the above description of the invention are intended to be included within the scope of the invention.
In addition, unless otherwise specifically indicated, the various raw materials, reagents, instruments and equipment used in the present invention may be obtained commercially or prepared by existing methods.
Example 1:
the preparation method of the 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound comprises the following steps:
1) 1.27g of 10mmol 5-methyl-3-nitro-1H-pyrazole was added to 20ml 98% concentrated sulfuric acid, cooled to room temperature after complete dissolution, then 10ml fuming nitric acid was gradually added dropwise, and the temperature was gradually raised to 80℃after complete addition to conduct nitration reaction. Pouring the reaction solution into 20mL of ice water after the reaction is finished, extracting with 50mL of diethyl ether, and performing rotary evaporation and vacuum drying to obtain 5-methyl-3, 4-dinitro-1H-pyrazole; taking 2mol 346mg of prepared 5-methyl-3, 4-dinitro-1H-pyrazole, adding 10ml of acetonitrile for complete dissolution, adding equivalent DBU, stirring at normal temperature for 3 hours, finally adding new THA, continuously stirring for reaction for 3 hours, and performing rotary evaporation and vacuum drying to obtain the compound of the formula II.
2) Dissolving 187mg of 1mmol of the compound of formula II in 5ml of acetonitrile, stirring until the compound is completely dissolved, adding 162mg1.5mmol of tert-butyl hypochloride, and reacting at-20 ℃ for 12h; after the reaction is finished, adding saturated sodium carbonate solution to adjust the pH to be neutral, adding water to extract by ethyl acetate after spin drying, and obtaining the 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound. The crystal structure of the 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound is shown in figure 1.
Wherein the structural formula of the 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound is as follows:
the structural formula of the compound of the formula II is as follows:
elemental analysis is carried out on the obtained 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound, so as to obtain the following elements in percentage by mass: 25.86% C, 1.69% H, 37.81% N and 34.64% O. And (3) performing nuclear magnetic analysis, wherein only one group of methyl peaks except the water peak and the solvent peak accord with the structural characteristics. The crystal structure diagram is combined again to prove that the prepared 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-binitro-1H-pyrazole) energetic compound is prepared.
Example 2:
the preparation method of the 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound comprises the following steps:
1) 1.27g of 10mmol 5-methyl-3-nitro-1H-pyrazole was added to 20ml 98% concentrated sulfuric acid, cooled to completion of dissolution, then 10ml fuming nitric acid was gradually added dropwise, and after completion of addition, the temperature was gradually raised to 80℃to conduct nitration reaction. Pouring the reaction solution into 50mL of ice water after the reaction is finished, extracting with 50mL of ethyl acetate, and performing rotary evaporation and vacuum drying to obtain 5-methyl-3, 4-dinitro-1H-pyrazole; taking 2mol 346mg of prepared 5-methyl-3, 4-dinitro-1H-pyrazole, adding 10ml of acetonitrile for complete dissolution, adding equivalent DBU, stirring at normal temperature for 3 hours, finally adding new THA, continuously stirring for reaction for 3 hours, and performing rotary evaporation and vacuum drying to obtain the compound of the formula II.
2) In 5ml acetonitrile, stirring until completely dissolved, adding 220mg of 1mmol of sodium dichloroisocyanurate and 0.5ml of acetic acid, reacting at 0 ℃ for 12 hours, adding saturated sodium carbonate solution to adjust pH to neutrality, spin-drying, adding water, and extracting with ethyl acetate to obtain the 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound.
Wherein the structural formula of the 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound is as follows:
the structural formula of the compound of the formula II is as follows:
the product structure identification result obtained in this example is the same as that of example 1.
Example 3:
the detonation performance of the 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) compound, such as detonation velocity, detonation pressure and the like, is predicted and calculated by adopting EXPL05 software (version 6.05); the decomposition temperature of the 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) compound prepared in example 1 was measured by a differential calorimeter, and the specific results are shown in Table 1.
TABLE 1
[a]Thermal decomposition temperature [ DEGC ]]；[b]Density [ g cm ] -3 ]；[c]Oxygen balance (C0) [%]；[d]Molar enthalpy of formation [ kJ. Mol ] -1 ]；[e]Detonation pressure [ GPa ]]；[f]Detonation velocity [ m.s ] -1 ]
The foregoing embodiment numbers of the present invention are merely for the purpose of description, and do not represent the advantages or disadvantages of the embodiments.
The embodiments of the present invention have been described above with reference to the accompanying drawings, but the present invention is not limited to the above-described embodiments, which are merely illustrative and not restrictive, and many forms may be made by those having ordinary skill in the art without departing from the spirit of the present invention and the scope of the claims, which are to be protected by the present invention.
Claims (10)
1. A polynitro nitrogen-rich energetic compound characterized by: the polynitro nitrogen-rich energetic compound is a 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound, and the structural formula is shown in formula I:
2. a process for the preparation of the polynitro nitrogen-rich energetic compound of claim 1, comprising the steps of:
1) Nitrifying 5-methyl-3-nitropyrazole under the action of concentrated sulfuric acid and fuming nitric acid and carrying out ammoniation reaction with THA to obtain a compound shown in a formula II;
2) Dissolving a compound of the formula II in acetonitrile, adding tert-butyl hypochlorite or a mixture of sodium dichloroisocyanurate and acetic acid under a low temperature condition after the compound is completely dissolved, adding a saturated sodium carbonate solution to adjust the pH to be neutral after the reaction is completed, extracting the mixture with ethyl acetate, and drying the mixture in vacuum to obtain the 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound;
the structural formula of the compound of the formula II is as follows:
3. a method for preparing a polynitro nitrogen-rich energetic compound as claimed in claim 2, wherein: adding the solution obtained after the nitration reaction in the step 1) into 20-50 mL of ice water, and extracting with diethyl ether/ethyl acetate.
4. A method for preparing a polynitro nitrogen-rich energetic compound as claimed in claim 2, wherein: in the step 1), the equivalent DBU is added after the nitration reaction and the extraction, and then the THA is added for ammoniation reaction.
5. A method for preparing a polynitro nitrogen-rich energetic compound as claimed in claim 2, wherein: the ratio of the compound of formula II to t-butyl hypochlorite in step 2) is 1mmol:1.5mmol.
6. A method for preparing a polynitro nitrogen-rich energetic compound as claimed in claim 2, wherein: the ratio of the compound of formula II to sodium dichloroisocyanurate and acetic acid in step 2) is 1mmol:1mmol:0.5ml.
7. The method for preparing the polynitrogen-rich energy-containing compound as defined in claim 5, wherein the method comprises the following steps: the low-temperature reaction condition of the compound of the formula II in the step 2) and the tert-butyl hypochlorite is-20 ℃ for 12 hours.
8. The method for preparing the polynitro nitrogen-rich energetic compound according to claim 6, wherein: the low-temperature reaction condition of the compound in the formula II in the step 2) and the mixture of sodium dichloroisocyanurate and acetic acid is 0 ℃ for 12 hours.
9. Use of a 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound according to any of claims 2 to 8 as nitrogen-enriched energetic material.
10. Use of a 1,1' (1, 2-diazenyl) -bis (5-methyl-3, 4-dinitro-1H-pyrazole) energetic compound according to claim 9 as nitrogen-rich energetic material as green high energy high temperature resistant primary explosive.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110590670A (en) * | 2019-09-24 | 2019-12-20 | 西安近代化学研究所 | 1, 2-bis (3, 5-dinitropyrazolyl) ethane compound and synthetic method thereof |
| CN111499586A (en) * | 2020-05-25 | 2020-08-07 | 北京理工大学重庆创新中心 | Synthesis method of 5,5' -triazene bridged bis (2-methyl-4-nitro-1, 2, 3-triazole) compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110590670A (en) * | 2019-09-24 | 2019-12-20 | 西安近代化学研究所 | 1, 2-bis (3, 5-dinitropyrazolyl) ethane compound and synthetic method thereof |
| CN111499586A (en) * | 2020-05-25 | 2020-08-07 | 北京理工大学重庆创新中心 | Synthesis method of 5,5' -triazene bridged bis (2-methyl-4-nitro-1, 2, 3-triazole) compound |
Non-Patent Citations (2)
| Title |
|---|
| Jing, Mei等.Theoretical investigation on the structure and performance of N,N'-azobis-polynitrodiazoles.Journal of Molecular Modeling.2014,第20卷(第4期),1-9. * |
| N-Diazo-Bridged Nitroazoles: Catenated Nitrogen-Atom Chains Compatible with Nitro Functionalities;Yin, Ping等;Chemistry - A European Journal;第20卷(第22期);6707-6712 * |
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