复合型含能基团结构和性能的理论研究

doi:10.6023/A26040105

摘要/Abstract

打破含能材料的发展瓶颈, 是近年来亟待攻克的难题. 本文尝试从设计新型含能基团的角度来探索新含能分子. 通过将传统含能基团进行组合, 使用密度泛函理论(DFT)方法计算了分子结构、初始热分解机理, 使用KJ方程和EXPLO5计算了爆轰性能, 筛选出39个含能基团, 初始分解能垒≥30 kcal•mol^-1. 其中5个已有实验合成的结构在热稳定性方面, 计算结果和实验十分吻合. 尝试用烷烃和多胺骨架进行分子设计, 所得分子密度>2.0 g•cm^-3, 爆速>8000 m•s^-1, 爆压>33 GPa. 分子内张力/位阻、以及N原子孤对电子的超共轭效应, 对最终含能分子的动力学稳定性具有重要影响.

关键词: 复合型含能基团, 含能材料, 分子设计, 理论研究, 动力学稳定性

Breaking the development bottlenecks of traditional energetic materials has become an urgent problem to be solved in recent years. In general, energetic materials are composed of energetic groups and molecular skeletons. At present, most design strategies for energetic molecules focus on the construction of novel molecular skeletons. Inspired by the unconventional complex energetic groups reported in the literature, this study focused on the design of new "composite energetic groups". A total of 72 initial structures were obtained by combining traditional energetic groups. Theoretical calculations on their molecular structures, initial thermal decomposition mechanisms were performed via density functional theory (DFT) using the Gaussian16 program. Excellent kinetic stability ensures a sufficiently high thermal decomposition temperature and favorable chemical stability, which are essential prerequisites for the practical application of energetic molecules. Identifying accurate trigger bonds and reliable decomposition mechanisms is critical for determining the initial decomposition energy barriers. Multiple potentially fractured chemical bonds and various cleavage pathways were considered, including homolysis, heterolysis, group migration, and elimination. The Kamlet-Jacobs (KJ) equation and the EXPLO5 program were adopted to calculate detonation velocity and detonation pressure. Subsequently, 39 energetic groups were screened out based on energetic performance and kinetic stability, all possessing an initial decomposition energy barrier of ≥30 kcal•mol^-1, among which 34 were unprecedented new groups. For five experimentally synthesized structures, detailed comparisons demonstrated that the calculated thermal stability results were in excellent agreement with experimental data. Furthermore, molecular design was carried out using alkane skeletons and polyamine skeletons. It is revealed that the intramolecular strain and steric hindrance dominated by alkane skeletons, as well as the hyperconjugation effect, exert a significant influence on the kinetic stability of the final energetic molecules. All these molecules exhibit a density >2.0 g•cm^-3, a detonation velocity >8000 m•s^-1, and a detonation pressure >33 GPa.

Key words: composite energetic groups, energetic materials, molecular design, theoretical study, kinetic stability

引用此文

马玲玲, 凌琳, 李玉学, 吕龙. 复合型含能基团结构和性能的理论研究[J]. 化学学报, 2026, 84(6): 828-839.

Lingling Ma, Lin Ling, Yuxue Li, Long Lu. Theoretical Study on the Structure and Properties of Composite Energetic Groups[J]. Acta Chimica Sinica, 2026, 84(6): 828-839.

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图/表 17

图1. (A)新型含能基团. 1E: 三硝基甲基偶氮; 1H: 一氟二二氟氨基甲基偶氮; 1J: 三二氟胺基甲基偶氮; 2A: 2-硝基氧化偶氮; 2E: 1-三硝基甲基氧化偶氮; 2F: 1-一氟二硝甲基氧化偶氮. 3A: 二硝酰胺; 7A: 二二氟胺基硝基甲基; (B)含复合型含能基团的代表化合物

Figure 1. (A) New energetic groups. 1E: Trinitromethylazo; 1H: Fluoro- bis(difluoroamino)methylazo; 1J: Tri(difluoroamino)methylazo; 2A: 2-Nitroazoxy; 2E: 1-Trinitromethylazoxy; 2F: 1-Fluorodinitromethyla- zoxy; 3A: Dinitramide; 7A: Bis(difluoramino)nitromethyl. (B) Representative compounds containing composite energetic groups

图2. (A)复杂含能基团可看作是简单传统含能基团组合而来; (B)利用矩阵进行组合构建“复合型含能基团”

Figure 2. (A) Complex energetic groups can be regarded as combinations of simple traditional energetic groups. (B) Matrices are used to construct new "composite energetic groups"

图3. 过去的设计策略重点在分子骨架, 本工作的设计策略重点在含能基团

Figure 3. Previous design strategies focused on molecular skeletons, whereas the design strategy in this work centers on energetic groups

图4. 新含能基团的构建矩阵. 绿色背景的结构引发键解离能垒大于30 kcal•mol-1; 红色背景的结构引发键解离能垒小于30 kcal•mol-1. 蓝色框中的结构有相关理论研究; 红色框中的结构有相关实验合成报道. 引发键解离能垒的计算详见结果与讨论部分. 最左侧列中红色的“R”表示组合时的取代位置

Figure 4. The Construction Matrix for new energetic groups. Structures with a green background have an activation energy barrier greater than 30 kcal•mol-1; structures with a red background have an activation energy barrier less than 30 kcal•mol-1. Structures in blue boxes have relevant theoretical studies; structures in red boxes have reported experimental synthesis. The calculation of the energy barrier of the trigger bond is detailed in the Results and Discussion section. The red letter "R" in the leftmost column denotes the substitution position for combination

图5. 典型的复合型含能基团结构示例. 键长单位: Å. 计算在M06-2X/6-311＋G(d,p)水平上进行

Figure 5. Typical examples of structures for composite energetic groups. Bond lengths are given in angstroms (Å). Calculated on the M06‑2X/6‑311＋G(d,p) level

Compd.	Barrier	∆_fH_Solid	ρ	Q/(cal•g^-1)	D/(km•s^-1)	P/GPa	Compd.	Barrier	∆_fH_Solid	ρ	Q/(cal•g^-1)	D/(km•s^-1)	P/GPa
1H	39.2	－156.2	1.94	1516	9.053	36.8	5I	40.2	－619.9	2.30	1617	10.098	50.6
2A	33.7	107.1	1.64	1644	8.881	33.0	5'D	33.9	524.6	1.65	1571	8.412	28.6
2B	40.4	52.4	1.70	1670	9.165	34.8	5'F	32.8	－509.3	2.09	1486	9.692	44.2
2E	35.9	136.5	1.88	1472	9.134	38.0	5'H	36.5	－641.6	2.35	1556	9.776	47.9
2F	51.1	－108.6	1.80	1410	8.800	33.2	5'I	39.2	－646.8	2.34	1649	10.136	51.5
2G	37.4	76.8	1.89	1703	9.606	41.0	6D	30.7	111.7	1.74	1243	8.578	31.9
2H	47.9	－200.3	1.98	1473	9.512	41.4	6E	32.2	－90.0	2.00	1292	9.134	39.4
2J	39.1	4.0	2.07	1719	10.107	47.9	6F	34.7	－316.4	1.94	1363	9.073	37.0
3F	32.7	－208.5	1.90	1321	8.982	35.8	6G	30.0	－127.6	2.02	1496	9.638	43.0
3G	30.7	－22.0	1.97	1483	9.566	41.7	6H	33.7	－388.4	2.09	1504	9.845	45.7
3H	33.2	－267.2	2.06	1509	9.900	45.9	6I	37.6	－370.8	2.12	1604	9.895	46.5
4B	37.7	－49.5	1.91	1142	6.618	19.0	6J	30.7	－177.0	2.15	1737	10.268	50.6
4E	34.5	－26.1	1.95	1479	9.475	40.6	7A	38.8	－210.1	1.96	1495	9.762	43.3
4F	39.4	－264.7	1.95	1573	9.663	42.2	7D	32.2	151.0	1.88	1663	9.172	37.1
4G	32.1	－79.6	2.02	1677	9.964	45.9	7F	35.9	－380.6	2.09	1511	9.852	45.7
4H	43.6	－335.0	2.12	1567	9.614	43.9	7G	31.8	－183.1	2.17	1732	10.325	51.4
4J	37.7	－134.6	2.19	1775	10.133	49.7	7H	39.6	－444.7	2.01	1592	8.956	36.8
5D	35.7	543.0	1.63	1464	8.174	27.9	7I	40.1	－435.1	2.20	1612	9.932	47.9
5F	31.6	－491.2	2.03	1312	9.248	39.5	7J	33.5	－249.0	2.27	1758	10.075	50.1
5H	32.0	－626.1	2.28	1424	9.956	49.0	CL-20	35.8	466.5	2.07	1618	9.796	46.1

Compd.	Barrier	∆_fH_Solid	ρ	Q/(cal•g^-1)	D/(km•s^-1)	P/GPa	Compd.	Barrier	∆_fH_Solid	ρ	Q/(cal•g^-1)	D/(km•s^-1)	P/GPa
1H	39.2	－156.2	1.94	1516	9.053	36.8	5I	40.2	－619.9	2.30	1617	10.098	50.6
2A	33.7	107.1	1.64	1644	8.881	33.0	5'D	33.9	524.6	1.65	1571	8.412	28.6
2B	40.4	52.4	1.70	1670	9.165	34.8	5'F	32.8	－509.3	2.09	1486	9.692	44.2
2E	35.9	136.5	1.88	1472	9.134	38.0	5'H	36.5	－641.6	2.35	1556	9.776	47.9
2F	51.1	－108.6	1.80	1410	8.800	33.2	5'I	39.2	－646.8	2.34	1649	10.136	51.5
2G	37.4	76.8	1.89	1703	9.606	41.0	6D	30.7	111.7	1.74	1243	8.578	31.9
2H	47.9	－200.3	1.98	1473	9.512	41.4	6E	32.2	－90.0	2.00	1292	9.134	39.4
2J	39.1	4.0	2.07	1719	10.107	47.9	6F	34.7	－316.4	1.94	1363	9.073	37.0
3F	32.7	－208.5	1.90	1321	8.982	35.8	6G	30.0	－127.6	2.02	1496	9.638	43.0
3G	30.7	－22.0	1.97	1483	9.566	41.7	6H	33.7	－388.4	2.09	1504	9.845	45.7
3H	33.2	－267.2	2.06	1509	9.900	45.9	6I	37.6	－370.8	2.12	1604	9.895	46.5
4B	37.7	－49.5	1.91	1142	6.618	19.0	6J	30.7	－177.0	2.15	1737	10.268	50.6
4E	34.5	－26.1	1.95	1479	9.475	40.6	7A	38.8	－210.1	1.96	1495	9.762	43.3
4F	39.4	－264.7	1.95	1573	9.663	42.2	7D	32.2	151.0	1.88	1663	9.172	37.1
4G	32.1	－79.6	2.02	1677	9.964	45.9	7F	35.9	－380.6	2.09	1511	9.852	45.7
4H	43.6	－335.0	2.12	1567	9.614	43.9	7G	31.8	－183.1	2.17	1732	10.325	51.4
4J	37.7	－134.6	2.19	1775	10.133	49.7	7H	39.6	－444.7	2.01	1592	8.956	36.8
5D	35.7	543.0	1.63	1464	8.174	27.9	7I	40.1	－435.1	2.20	1612	9.932	47.9
5F	31.6	－491.2	2.03	1312	9.248	39.5	7J	33.5	－249.0	2.27	1758	10.075	50.1
5H	32.0	－626.1	2.28	1424	9.956	49.0	CL-20	35.8	466.5	2.07	1618	9.796	46.1

表1. 引发键解离能垒≥30 kcal•mol-1的新含能基团的计算结果. Barrier: 引发键解离能垒(kcal•mol-1); ∆fHSolid固态生成焓(kJ•mol-1, 详见SI), 密度ρ (g•cm-3), 爆热Q, KJ方程计算的爆速D和爆压P

Table 1. Calculated results for new energetic groups with trigger bond energy barrier≥30 kcal•mol-1. Barrier: Trigger bond energy barrier (in kcal•mol-1); ΔHf: Solid-state enthalpy of formation (in kJ•mol-1, See SI); ρ: Density (g•cm-3); Q: Detonation heat; D: Detonation velocity; P: Detonation pressure

图6. 1E的初始分解机理. (1) 1E-Path-a-Hetero, Bond-a的异裂; (2) 1E-Path-b-Homo, Bond-b的均裂; (3) 1E-Path-b-NO2-1,3-shift, NO2的1,3迁移; (4) 1E-Path-b-HONO-Elimination, HONO消除. 键长单位: Å. 计算在M06-2X/6-311＋G(d,p)水平上进行

Figure 6. The initial decomposition mechanism of 1E: (1) 1E-Path-a-Hetero: Heterolytic cleavage of Bond-a; (2) 1E-Path-b-Homo: Homolytic cleavage of Bond-b; (3) 1E-Path-b-NO2-1,3-shift: 1,3-migration of the NO2 group; (4) 1E-Path-b-HONO-Elimination: HONO elimination reaction. Selected bond lengths are in angstroms (Å), calculated at the M06-2X/6-311＋G(d,p) level

图7. 图6反应路径中的重要结构. 键长单位: Å. 计算在M06-2X/6-311＋G(d,p)水平上进行

Figure 7. Key structures in the reaction pathways of Figure 6. Selected bond lengths are in angstroms (Å), calculated at the M06-2X/6-311＋G(d,p) level

图8. 2E的初始分解机理. (1) 2E-Path-a-Hetero, Bond-a的异裂; (2) 2E-Path-a-Homo, Bond-a的均裂; (3) 2E-Path-b-NO2-1,3-shift, NO2的1,3迁移; (4) 2E-Path-b-Homo, Bond-b的均裂. 键长单位: Å. 计算在M06-2X/6-311＋G(d,p)水平上进行

Figure 8. The Initial decomposition mechanism of 2E: (1) 2E-Path-a-Hetero: Heterolytic cleavage of Bond-a; (2) 2E-Path-a-Homo: Homolytic cleavage of Bond-a; (3) 2E-Path-b-NO2-1,3-shift: 1,3-migration of the NO2 group; (4) 2E-Path-b-Homo: Homolytic cleavage of Bond-b (Å), calculated at the M06-2X/6-311＋G(d,p) level

图9. 图8反应路径中的重要结构. 键长单位: Å. 计算在M06-2X/6-311＋G(d,p)水平上进行

Figure 9. Key structures in the reaction pathways of Figure 8. Selected bond lengths are in angstroms (Å), calculated at the M06-2X/6-311＋G(d,p) level

Group	Compd.	Stability	Ref.	Barrier/ (kcal•mol^-1)
1E	1E-1	室温下几天内分解	[11]	20.3
1H	1H-3	“沸点81 ℃”, “remarkable thermal stability”	[13]	39.2
1J	1J-1	核磁\色谱观察到很少量样品	[13]	21.6
2A	2A-4	DSC, T_p=164 ℃	[21]	33.7
2E	BTNAF	DSC, T_p=183.6 ℃	[34]	35.9
2F	FDNAF	DSC, T_p=233.4 ℃	[38]	51.1
3A	3A-1	在熔点分解(71~72 ℃)	[39]	26.7
7A	7A-F	室温数月没有观察到分解	[40]	38.8

表2. 实验已合成的含复合型含能基团的化合物的热稳定性与引发键分解能垒计算值的比较

Table 2. Comparison between the thermal stability of experimentally synthesized compounds containing composite energetic groups and the calculated decomposition energy barriers of trigger bonds

图10. 含能基团7A和烷烃骨架、多胺骨架构成的含能分子

Figure 10. Energetic molecules composed of energetic group 7A with alkane skeletons and nitramine skeletons

Compd.	K-J Function		EXPLO5
Compd.	D	P	D	P	I_sp
7A	9762	43.3	8427	38.8	280.2
7A-PETN	10225	50.4	8679	44.1	270.3
7A-TMETN	9944	46.3	8746	43.9	275.4
7A-RDX	10145	49.2	8867	45.0	268.9
7A-HMX	10364	52.2	9007	47.1	268.9
7A-TNIW	10297	50.8	9443	48.6	278.5
Cl-20	9796	46.1	9773	44.8	272.1

表3. 新含能分子的爆速(D, m•s-1)、爆压(P, GPa)和比冲(Isp, s)

Table 3. Detonation velocity (D, m•s-1), detonation pressure (P, GPa), and specific impulse (Isp, s) of the novel energetic molecules

Compd.	∆_fH_Solid	ρ	a/Å	b/Å	c/Å	Barrrier
7A	－210.1	1.96	1.480	1.541	—	38.8
7A-PETN	－513.0	2.17	1.491	1.536	1.539	33.3
7A-TMETN	－497.9	2.07	1.489	1.543	1.529	38.2
7A-RDX	－199.1	2.14	1.523	1.563	1.382	27.8
7A-HMX	－261.2	2.20	1.515	1.576	1.404	28.7
7A-TNIW	288.1	2.14	1.507	1.585	1.403	29.9

表4. 新含能分子的生成焓(ΔHf (kJ•mol-1))、密度(g•cm-3)、关键键长(Å)和引发键解离能垒(kcal•mol-1)

Table 4. Enthalpy of formation (∆fHSolid, kJ•mol-1), density (g•cm-3), key bond lengths (Å), and trigger bond energy barriers (kcal•mol-1) of the new energetic molecules

图11. 含能分子7A-PETN、7A-TMETN和7A-RDX的初始分解机理

Figure 11. Initial decomposition mechanisms of energetic molecules 7A-PETN, 7A-TMETN and 7A-RDX

图12. 基团7A和含能分子7A-PETN、7A-TMETN代表性结构的原子距离(Å)和键角(度), “C”表示中心碳原子.

Figure 12. Selected atomic distances (Å) and bond angles (in degree) of the energetic group 7A and energetic molecules 7A-PETN, 7A-TMETN; atoms marked with C is the central carbon atom.

图13. (A)过渡态7A-a-TS和(B) 7A-DMA-a-TS的自旋密度分布以及与超共轭有关的分子轨道

Figure 13. Spin density distribution of transition states and molecular orbitals related to hyperconjugation of (A) 7A-a-TS and (B) 7A-DMA-a-TS

参考文献 51

[1]	Bottaro, J. C. Chemistry & Industry 1996, 249.
[2]	Wang, W. J. J. Solid Rocket Technol. 2003, 26, 42 (in Chinese).
	(王文俊, 固体火箭技术, 2003, 26, 42.)
[3]	Sikder, A. K.; Sikder, N. J. Hazard. Mater. 2004, 112, 1. pmid: 15225926
[4]	Huang, H.; Wang, Z. S.; Huang, H. J.; Li, J. S. Chin. J. Explos. Propellants 2005, 28, 9 (in Chinese).
	(黄辉, 王泽山, 黄亨建, 李金山. 火炸药学报, 2005, 28, 9.)
[5]	Klapötk, T. M. Chemistry of High Energy Materials, Translated by Zhang, J. G.; Qin, J., Beijing Institute of Technology Press, Beijing, 2016 (in Chinese).
	(Thomas, M Klapötk著, 高能材料化学, 张建国, 秦涧译, 北京理工大学出版社, 北京, 2016.)
[6]	Trache, D.; Klapötke, T. M.; Maiz, L.; Abd-Elghany, M.; DeLuca, L. T. Green Chem. 2017, 19, 4711. doi: 10.1039/C7GC01928A
[7]	Huang, H. J.; Huang, H. Materials China 2018, 37, 889 (in Chinese).
	(黄亨建, 黄辉, 中国材料进展, 2018, 37, 889.)
[8]	Dong, H. S. Chin. J. Energ. Mater. 2004, A01, 1 (in Chinese).
	(董海山, 含能材料, 2004, A01, 1.)
[9]	Tian, J. J.; Zhang, Q. H.; Li, J. S. Chin. J. Energ. Mater. 2016, 24, 1 (in Chinese).
	(田均均, 张庆华, 李金山, 含能材料, 2016, 24, 1 )
[10]	Du, Y.; Qu, Z. K.; Wang, H. C.; Cui, H.; Wang, X. J. Explos. Pyrotech. 2021, 46, 860. doi: 10.1002/prep.v46.6
[11]	Pankov, A.; Pevzner, M.; Bagal, L. Khim. Geterotsikl. Soedin. 1972, 8, 649.
[12]	Hynes, J. B.; Austin, T. E.; Bigelow, L. A. Inorg. Chem. 1968, 7, 1647. doi: 10.1021/ic50066a037
[13]	Hynes, J. B.; Austin, T. E.; Bigelow, L. Inorg. Chem. 1972, 11, 418. doi: 10.1021/ic50108a045
[14]	Churakov, A. M.; Ioffe, S. L.; Tartakovsky, V. A. Mendeleev Commun. 1996, 6, 20. doi: 10.1070/MC1996v006n01ABEH000560
[15]	Churakov, A. M.; Semenov, S. E.; Ioffe, S. L.; Strelenko, Y. A.; Tartakovsky, V. A. Russ. Chem. Bull. 1997, 46, 1042. doi: 10.1007/BF02496149
[16]	Sheremetev, A. B.; Semenov, S. E.; Kuzmin, V. S.; Strelenko, Y. A.; Ioffe, S. L. Chem. - Eur. J. 1998, 4, 1023. doi: 10.1002/(ISSN)1521-3765
[17]	Li, H.; Wang, B. Z.; Li, X. Z.; Lai, W. P.; Fan, X. Z.; Tong, J. F. Bull. Korean Chem. Soc. 2013, 34, 686. doi: 10.5012/bkcs.2013.34.2.686
[18]	Hui, L. I.; Wang, B. Z. Chin. J. Energ. Mater. 2014, 22, 880.
[19]	Wang, Y.; Li, S.; Li, Y.; Zhang, R.; Wang, D.; Pang, S. J. Mater. Chem. A 2014, 2, 20806. doi: 10.1039/C4TA04716H
[20]	Leonov, N. E.; Klenov, M. S.; Anikin, O. V.; Churakov, A. M.; Strelenko, Y. A.; Monogarov, K. A.; Tartakovsky, V. A.. Eur. J. Org. Chem. 2019, 2019, 91.
[21]	Anikin, O. V.; Leonov, N. E.; Klenov, M. S.; Churakov, A. M.; Voronin, A. A.; Muravyev, N. V.; Strelenko, Y. A.; Fedyanin, I. V.; Tartakovsky, V. A. Eur. J. Org. Chem. 2019, 2019, 4189. doi: 10.1002/ejoc.201900314
[22]	Klenov, M. S.; Leonov, N. E.; Guskov, A. A.; Churakov, A. M.; Strelenko, Y. A.; Tartakovsky, V. A. Russ. Chem. Bull. 2019, 68, 1798. doi: 10.1007/s11172-019-2628-7
[23]	Leonov, N. E.; Klenov, M. S.; Anikin, O. V.; Churakov, A. M.; Strelenko, Y. A.; Voronin, A. A.; Lempert, D. B.; Muravyev, N. V.; Fedyanin, I. V.; Semenov, S. E.; Tartakovsky, V. A. ChemistrySelect 2020, 5, 12243. doi: 10.1002/slct.v5.39
[24]	Lukýanov, O. A.; Pokhvisneva, G. V.; Ternikova, T. V.; Shlykova, N. I.; Shagaeva, M. E. Russ. Chem. Bull. 2011, 60, 1703. doi: 10.1007/s11172-011-0254-0
[25]	Luk’yanov, O. A.; Parakhin, V. V. Russ. Chem. Bull. 2012, 61, 1582. doi: 10.1007/s11172-012-0210-7
[26]	Luk’yanov, O. A.; Parakhin, V. V.; Pokhvisneva, G. V., Ternikova, T. V. Russ. Chem. Bull. 2012, 61, 355. doi: 10.1007/s11172-012-0049-y
[27]	Luk’yanov, O. A.; Pokhvisneva, G. V.; Ternikova, T. V.; Shlykova, N. I. Russ. Chem. Bull. 2012, 61, 360. doi: 10.1007/s11172-012-0050-5
[28]	Luk’yanov, O. A.; Pokhvisneva, G. V.; Ternikova, T. V. Russ. Chem. Bull. 2012, 61, 1783. doi: 10.1007/s11172-012-0245-9
[29]	Parakhin, V. V.; Luk’yanov, O. A. Russ. Chem. Bull. 2013, 62, 516. doi: 10.1007/s11172-013-0071-8
[30]	Luk’yanov, O. A.; Pokhvisneva, G. V.; Ternikova, A. T. Russ. Chem. Bull. 2015, 64, 137. doi: 10.1007/s11172-015-0832-7
[31]	Parakhin, V. V.; Luk’yanov, O. A. Russ. Chem. Bull. 2016, 65, 295. doi: 10.1007/s11172-016-1301-7
[32]	Zhang, J. R.; Bi, F. Q.; Wang, B. Z.; Zhang, J. L.; Zhai, L. J.; Li, Y. N.; Jia, S. Y. Chin. J. Explos. Propellants. 2016, 39, 12 (in Chinese).
	(张家荣, 毕福强, 王伯周, 张俊林, 翟连杰, 李亚南, 贾思媛, 火炸药学报, 2016, 39, 12.) doi: 10.14077/j.issn.1007-7812.2016.06.002
[33]	Bi, F. Q.; Wang, Y.; Wang, B. Z.; Zhang, J. R.; Zhang, J. L.; Zhai, L. J.; Li, X. Z. Chin. J. Energ. Mater. 2016, 24, 1063 (in Chinese).
	(毕福强, 王玉, 王伯周, 张家荣, 张俊林, 翟连杰, 李祥志, 含能材料, 2016, 24, 1063.)
[34]	Zhang, J. R.; Bi, F. Q.; Wang, B. Z.; Lian, P.; Zhai, L. J.; Jia, S. Y. Chin. J. Explos. Propellants 2017, 25, 701.
[35]	Zhang, J. R.; Bi, F. Q.; Wang, B. Z.; Zhang, J. L.; Jia, S. Y. Chin. J. Explos. Propellants. 2017, 40, 45 (in Chinese).
	(张家荣, 毕福强, 张俊林, 贾思媛, 火炸药学报, 2017, 40, 45.) doi: 10.14077/j.issn.1007-7812.2017.05.008
[36]	Zhang, J. R.; Bi, F. Q.; Zhang, J. L.; Jia, S. Y.; Wang, B. Z. Chin. J. Energ. Mater. 2021, 29, 798 (in Chinese).
	(张家荣, 毕福强, 张俊林, 贾思媛, 王伯周, 含能材料, 2021, 29, 798.)
[37]	Luk’yanov, O. A.; Pokhvisneva, G. V.; Ternikova, A. T. Russ. Chem. Bull. 2015, 64, 83. doi: 10.1007/s11172-015-0824-7
[38]	Zhang, J. R.; Bi, F. Q.; Lian, P.; Zhang, J. L.; Wang, B. Z. Chin. J. Org. Chem. 2017, 37, 2736 (in Chinese).
	(张家荣, 毕福强, 廉鹏, 张俊林, 王伯周, 有机化学, 2017, 37, 2736.) doi: 10.6023/cjoc201701014
[39]	Hamel, E. E.; Olsen, R. E. US3428667A, 1969.
[40]	Talbott, R. L.; Koshar, R. J. US3387033 A, 1968.
[41]	Cui, Y. K.; Cheng, S. F.; Ling, L.; Li, Y. X.; Lu, L. Acta Chim. Sinica 2024, 82, 377 (in Chinese). doi: 10.6023/A24010017
	(崔勇康, 成守飞, 凌琳, 李玉学, 吕龙. 化学学报, 2024, 82, 377.)
[42]	Kamlet, M. J.; Hurwitz, H. J. Chem. Phys. 1968, 48, 3685.
[43]	Keshavarz, M. H.; Pouretedal, H. R. Thermochim. Acta 2004, 414, 203. doi: 10.1016/j.tca.2003.11.019
[44]	Sućeska, M. Propellants, Explos., Pyrotech. 1999, 24, 280. doi: 10.1002/(ISSN)1521-4087
[45]	Li, W. X. Chem. Bull. 1988, 6, 19 (in Chinese).
	(李卫星, 化学通报, 1988, 6, 19.)
[46]	Peterson, J. P.; Winter, A. H. J. Am. Chem. Soc. 2019, 141, 12901. doi: 10.1021/jacs.9b06576 pmid: 31352783
[47]	Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Petersson, G. A.; Nakatsuji, H.; Li, X.; Caricato, M.; Marenich, A. V.; Bloino, J.; Janesko, B. G.; Gomperts, R.; Mennucci, B.; Hratchian, H. P.; Ortiz, J. V.; Izmaylov, A. F.; Sonnenberg, J. L.; Williams-Young, D.; Ding, F.; Lipparini, F.; Egidi, F.; Goings, J.; Peng, B.; Petrone, A.; Hen derson, T.; Ranasinghe, D.; Zakrzewski, V. G.; Gao, J.; Rega, N.; Zheng, G.; Liang, W.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Throssell, K.; Montgomery, J. A. Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M. J.; Heyd, J. J.; Brothers, E. N.; Kudin, K. N.; Staroverov, V. N.; Keith, T. A.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A. P.; Burant, J. C.; Iyengar, S. S.; To masi, J.; Cossi, M.; Millam, J. M.; Klene, M.; Adamo, C.; Cammi, R.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Farkas, O.; For esman, J. B.; Fox, D. J.,Gaussian 16, Revision A.03, Gaussian, Inc., Wallingford CT, 2016.
[48]	Bader, R. F.; Carroll, M. T.; Cheeseman, J. R.; Chang, C. J. Am. Chem. Soc. 1987, 109, 7968. doi: 10.1021/ja00260a006
[49]	Rice, B. M.; Hare, J. J.; Byrd, E. F. J. Phys. Chem. A 2007, 111, 10874. doi: 10.1021/jp073117j
[50]	Hehre, W. J.; Ditchfield, R.; Radom, L.; Pople, J. A. J. Am. Chem. Soc. 1970, 92, 4796. doi: 10.1021/ja00719a006
[51]	Ling, L.; Wang, J.; Li, J.; Li, Y. X.; Lu, L. Chin. J. Org. Chem. 2023, 43, 285 (in Chinese). doi: 10.6023/cjoc202206027
	(凌琳, 王健, 李婧, 李玉学, 吕龙, 有机化学, 2023, 43, 285.) doi: 10.6023/cjoc202206027