有机化学 ›› 2021, Vol. 41 ›› Issue (4): 1466-1488.DOI: 10.6023/cjoc202009019 上一篇 下一篇
综述与进展
李光磊a,b, 黄海丰b,c,*(), 杨军b,*(), 段红珍a,*()
收稿日期:
2020-09-08
修回日期:
2020-09-28
发布日期:
2020-11-04
通讯作者:
黄海丰, 杨军, 段红珍
基金资助:
Guanglei Lia,b, Haifeng Huangb,c,*(), Jun Yangb,*(), Hongzhen Duana,*()
Received:
2020-09-08
Revised:
2020-09-28
Published:
2020-11-04
Contact:
Haifeng Huang, Jun Yang, Hongzhen Duan
About author:
Supported by:
文章分享
吡唑环上有三个可修饰的碳位点和一个可修饰的NH位点, 通过对这四个位点的修饰(主要是引入硝基、硝胺基、氨基、羟基以及形成稠环等), 可设计出种类丰富的吡唑含能化合物. 同时, 相对于2,4,6-三硝基甲苯(TNT)、黑索金(RDX)、奥克托今(HMX)等常规含能化合物, 吡唑含能化合物具有氮含量高、生成焓高及感度低等优势. 近年来, 国内外基于吡唑骨架设计并合成了大量吡唑含能离子盐, 其中很多种化合物表现出高能及钝感等特性. 按单环吡唑含能离子盐、联环吡唑含能离子盐及稠环吡唑含能离子盐, 分类综述了近年来所报道的吡唑含能离子盐的合成及性能, 并对该类化合物的应用前景进行了展望.
李光磊, 黄海丰, 杨军, 段红珍. 吡唑含能离子盐的合成研究进展[J]. 有机化学, 2021, 41(4): 1466-1488.
Guanglei Li, Haifeng Huang, Jun Yang, Hongzhen Duan. Progress in the Synthesis of Energetic Salts Based on Pyrazole[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1466-1488.
Compd. | Tma/℃ | Tdb/℃ | dc/(g?cm–3) | ΔfHd/(kJ?mol–1)/(kJ?g–1) | Pe/GPa | Df/(m?s–1) | ISg/J | FSh/N | |
---|---|---|---|---|---|---|---|---|---|
2a | — | 224 | 1.73 | 60.5/0.28 | 29.9 | 8461 | 40 | — | |
2b | 158 | 167 | 1.69 | 299.0/1.10 | 25.6 | 7871 | >40 | — | |
2c | 171 | 171 | 1.71 | 273.5/0.95 | 26.0 | 7972 | >40 | — | |
2d | 168 | 168 | 1.77 | 401.2/1.40 | 31.9 | 8543 | >40 | — | |
2e | 188 | 196 | 1.76 | 235.6/0.78 | 27.7 | 8216 | >40 | — | |
2f | — | 243 | 1.68 | 452.3/0.75 | 24.3 | 7817 | >40 | — | |
2g | 163 | 235 | 1.66 | 28.3/0.11 | 24.7 | 7865 | >40 | — | |
2h | 136 | 222 | 1.69 | 133.6/0.48 | 26.9 | 8134 | >40 | — | |
2i | 206 | 206 | 1.76 | 355.0/1.12 | 28.8 | 8359 | >40 | — | |
2j | 166 | 219 | 1.61 | 375.0/1.19 | 23.7 | 7586 | >40 | — | |
2k | 120 | 167 | 1.64 | 459.8/1.45 | 25.2 | 7922 | 35 | — | |
2l | 122 | 197 | 1.62 | 246.5/0.84 | 25.3 | 7983 | >40 | — | |
2m | 125 | 184 | 1.65 | 352.7/1.15 | 27.2 | 8236 | >40 | — | |
4 | — | 176 | 1.82 | 35.1/0.15 | 35.1 | 8676 | 6 | — | |
6a | — | 171 | 1.72 | 3.1/0.01 | 28.8 | 8176 | >40 | — | |
6b | — | 140 | 1.73 | 274.9/0.95 | 29.5 | 8175 | >40 | — | |
6c | — | 132 | 1.73 | 250.5/0.83 | 29.2 | 8177 | >40 | — | |
6d | — | 118 | 1.74 | 381.6/1.26 | 30.8 | 8345 | >40 | — | |
6e | — | 186 | 1.76 | 213.7/0.67 | 29.7 | 8261 | >40 | — | |
6f | — | 185 | 1.77 | 331.9/1.00 | 31.1 | 8442 | >40 | — | |
11a | — | 147 | 1.80 | 54.2/0.19 | 37.4 | 9013 | 30 | — | |
11b | — | 171 | 1.75 | 274.7/0.97 | 33.8 | 8917 | 5 | — | |
11c | — | 115 | 1.64 | 544.6/1.53 | 25.3 | 7921 | >40 | — | |
11d | — | 167 | 1.75 | 496.6/1.29 | 27.9 | 8244 | >40 | — | |
11e | 103 | 118 | 1.74 | 762.9/1.98 | 29.7 | 8452 | >40 | — | |
11f | — | 170 | 1.71 | 452.4/1.09 | 27.1 | 8196 | >40 | — | |
11g | — | 194 | 1.71 | 718.2/1.61 | 27.9 | 8342 | >40 | — | |
11h | — | 229 | 1.66 | –0.8/–0.01 | 24.3 | 7920 | >40 | — | |
11i | — | 180 | 1.64 | 227.9/0.62 | 25.5 | 8117 | >40 | — | |
11j | — | 178 | 1.65 | 464.1/1.17 | 27.5 | 8385 | >40 | — | |
11k | — | 172 | 1.65 | 701.5/1.65 | 28.9 | 8581 | 23 | — | |
11l | 132 | 189 | 1.69 | –362.8/–0.86 | 23.3 | 7713 | >40 | — | |
11m | — | 144 | 1.81 | –108.6/–0.35 | 30.4 | 8378 | 5 | — | |
11n | — | 166 | 1.72 | –229.4/–0.72 | 24.4 | 7799 | >40 | — | |
15a | — | 141 | 1.85 | 264.2/0.77 | 40.2 | 9410 | 8 | 80 | |
15b | — | 152 | 1.75 | 489.3/1.42 | 35.7 | 9066 | 5 | 60 | |
18a | — | 166 | 1.86 | 193.7/0.77 | 38.5 | 9195 | 10 | 80 | |
18b | — | 180 | 1.86 | 293.7/1.17 | 38.7 | 9176 | 10 | 120 | |
18c | — | 171 | 1.72 | 122.3/0.44 | 28.3 | 8319 | 40 | 360 | |
Compd. | Tma/℃ | Tdb/℃ | dc/(g?cm–3) | ΔfHd/(kJ?mol–1)/(kJ?g–1) | Pe/GPa | Df/(m?s–1) | ISg/J | FSh/N | |
18d | — | 200 | 1.79 | 232.3/0.80 | 32.2 | 8745 | 24 | 160 | |
18e | — | 177 | 1.78 | 488.9/1.62 | 31.9 | 8645 | 20 | 160 | |
18f | — | 183 | 1.81 | 320.4/1.01 | 31.5 | 8629 | 30 | 240 | |
18g | — | 153 | 1.84 | 720.5/2.27 | 37.4 | 9170 | 6 | 60 | |
18h | — | 142 | 1.77 | 416.7/0.79 | 32.8 | 8652 | 20 | 120 | |
18i | — | 130 | 1.88 | 450.0/1.34 | 39.5 | 9237 | 8 | 80 | |
22a | — | 244 | 1.62 | –147.3/–0.92 | 20.3 | 7776 | 28 | 240 | |
22b | — | 181 | 1.64 | –93.3/–0.53 | 22.8 | 7929 | 26 | 240 | |
22c | — | 223 | 1.63 | 8.8/0.05 | 23.8 | 8339 | 23 | 240 | |
23b | — | 204 | 1.71 | 12.4/0.05 | 26.4 | 8200 | 40 | 360 | |
23c | — | 169 | 1.71 | 219.8/0.79 | 28.0 | 8540 | 40 | 360 | |
23d | — | 214 | 1.75 | 337.2/1.15 | 30.7 | 8877 | 40 | 360 | |
26a | — | 167 | 1.68 | 68.7/0.36 | 28.2 | 8279 | 10 | 360 | |
26b | — | 180 | 1.70 | 27.0/0.12 | 25.1 | 8063 | 30 | 360 | |
26c | 132 | 169 | 1.64 | 144.9/0.58 | 24.7 | 8021 | 10 | 360 | |
27a | — | 224 | 1.62 | –253.4/–1.21 | 24.4 | 7909 | 30 | 288 | |
27b | — | 266 | 1.68 | 7.8/0.03 | 24.2 | 7935 | 40 | 360 | |
27c | — | 131 | 1.68 | 115.2/0.46 | 25.7 | 8159 | 10 | 360 | |
31 | — | 129 | 1.80 | 194.8/0.78 | 33.8 | 8790 | 7 | 192 | |
36a | — | 141 | 1.78 | 85.4/0.36 | 33.0 | 8601 | >20 | 192 | |
36b | — | 166 | 1.80 | 135.5/0.54 | 34.1 | 8700 | >20 | 162 | |
36c | — | 161 | 1.72 | 43.8/0.16 | 28.7 | 8256 | >20 | 240 | |
36d | — | 140 | 1.71 | 231.4/0.78 | 30.1 | 8480 | >20 | 252 | |
TNTi | 81 | 290 | 1.65 | –55.5/–0.24 | 23.5 | 7459 | 15 | 353 | |
RDXi | 205 | 210 | 1.81 | 86.3/0.39 | 38.0 | 8983 | 7.5 | 120 | |
HMXi | 275 | 279 | 1.90 | 116.1/0.39 | 41.5 | 9221 | 7 | 112 | |
CL-20i | — | 215 | 2.03 | 365.4/0.83 | 46.7 | 9455 | 4 | 48 |
Compd. | Tma/℃ | Tdb/℃ | dc/(g?cm–3) | ΔfHd/(kJ?mol–1)/(kJ?g–1) | Pe/GPa | Df/(m?s–1) | ISg/J | FSh/N | |
---|---|---|---|---|---|---|---|---|---|
2a | — | 224 | 1.73 | 60.5/0.28 | 29.9 | 8461 | 40 | — | |
2b | 158 | 167 | 1.69 | 299.0/1.10 | 25.6 | 7871 | >40 | — | |
2c | 171 | 171 | 1.71 | 273.5/0.95 | 26.0 | 7972 | >40 | — | |
2d | 168 | 168 | 1.77 | 401.2/1.40 | 31.9 | 8543 | >40 | — | |
2e | 188 | 196 | 1.76 | 235.6/0.78 | 27.7 | 8216 | >40 | — | |
2f | — | 243 | 1.68 | 452.3/0.75 | 24.3 | 7817 | >40 | — | |
2g | 163 | 235 | 1.66 | 28.3/0.11 | 24.7 | 7865 | >40 | — | |
2h | 136 | 222 | 1.69 | 133.6/0.48 | 26.9 | 8134 | >40 | — | |
2i | 206 | 206 | 1.76 | 355.0/1.12 | 28.8 | 8359 | >40 | — | |
2j | 166 | 219 | 1.61 | 375.0/1.19 | 23.7 | 7586 | >40 | — | |
2k | 120 | 167 | 1.64 | 459.8/1.45 | 25.2 | 7922 | 35 | — | |
2l | 122 | 197 | 1.62 | 246.5/0.84 | 25.3 | 7983 | >40 | — | |
2m | 125 | 184 | 1.65 | 352.7/1.15 | 27.2 | 8236 | >40 | — | |
4 | — | 176 | 1.82 | 35.1/0.15 | 35.1 | 8676 | 6 | — | |
6a | — | 171 | 1.72 | 3.1/0.01 | 28.8 | 8176 | >40 | — | |
6b | — | 140 | 1.73 | 274.9/0.95 | 29.5 | 8175 | >40 | — | |
6c | — | 132 | 1.73 | 250.5/0.83 | 29.2 | 8177 | >40 | — | |
6d | — | 118 | 1.74 | 381.6/1.26 | 30.8 | 8345 | >40 | — | |
6e | — | 186 | 1.76 | 213.7/0.67 | 29.7 | 8261 | >40 | — | |
6f | — | 185 | 1.77 | 331.9/1.00 | 31.1 | 8442 | >40 | — | |
11a | — | 147 | 1.80 | 54.2/0.19 | 37.4 | 9013 | 30 | — | |
11b | — | 171 | 1.75 | 274.7/0.97 | 33.8 | 8917 | 5 | — | |
11c | — | 115 | 1.64 | 544.6/1.53 | 25.3 | 7921 | >40 | — | |
11d | — | 167 | 1.75 | 496.6/1.29 | 27.9 | 8244 | >40 | — | |
11e | 103 | 118 | 1.74 | 762.9/1.98 | 29.7 | 8452 | >40 | — | |
11f | — | 170 | 1.71 | 452.4/1.09 | 27.1 | 8196 | >40 | — | |
11g | — | 194 | 1.71 | 718.2/1.61 | 27.9 | 8342 | >40 | — | |
11h | — | 229 | 1.66 | –0.8/–0.01 | 24.3 | 7920 | >40 | — | |
11i | — | 180 | 1.64 | 227.9/0.62 | 25.5 | 8117 | >40 | — | |
11j | — | 178 | 1.65 | 464.1/1.17 | 27.5 | 8385 | >40 | — | |
11k | — | 172 | 1.65 | 701.5/1.65 | 28.9 | 8581 | 23 | — | |
11l | 132 | 189 | 1.69 | –362.8/–0.86 | 23.3 | 7713 | >40 | — | |
11m | — | 144 | 1.81 | –108.6/–0.35 | 30.4 | 8378 | 5 | — | |
11n | — | 166 | 1.72 | –229.4/–0.72 | 24.4 | 7799 | >40 | — | |
15a | — | 141 | 1.85 | 264.2/0.77 | 40.2 | 9410 | 8 | 80 | |
15b | — | 152 | 1.75 | 489.3/1.42 | 35.7 | 9066 | 5 | 60 | |
18a | — | 166 | 1.86 | 193.7/0.77 | 38.5 | 9195 | 10 | 80 | |
18b | — | 180 | 1.86 | 293.7/1.17 | 38.7 | 9176 | 10 | 120 | |
18c | — | 171 | 1.72 | 122.3/0.44 | 28.3 | 8319 | 40 | 360 | |
Compd. | Tma/℃ | Tdb/℃ | dc/(g?cm–3) | ΔfHd/(kJ?mol–1)/(kJ?g–1) | Pe/GPa | Df/(m?s–1) | ISg/J | FSh/N | |
18d | — | 200 | 1.79 | 232.3/0.80 | 32.2 | 8745 | 24 | 160 | |
18e | — | 177 | 1.78 | 488.9/1.62 | 31.9 | 8645 | 20 | 160 | |
18f | — | 183 | 1.81 | 320.4/1.01 | 31.5 | 8629 | 30 | 240 | |
18g | — | 153 | 1.84 | 720.5/2.27 | 37.4 | 9170 | 6 | 60 | |
18h | — | 142 | 1.77 | 416.7/0.79 | 32.8 | 8652 | 20 | 120 | |
18i | — | 130 | 1.88 | 450.0/1.34 | 39.5 | 9237 | 8 | 80 | |
22a | — | 244 | 1.62 | –147.3/–0.92 | 20.3 | 7776 | 28 | 240 | |
22b | — | 181 | 1.64 | –93.3/–0.53 | 22.8 | 7929 | 26 | 240 | |
22c | — | 223 | 1.63 | 8.8/0.05 | 23.8 | 8339 | 23 | 240 | |
23b | — | 204 | 1.71 | 12.4/0.05 | 26.4 | 8200 | 40 | 360 | |
23c | — | 169 | 1.71 | 219.8/0.79 | 28.0 | 8540 | 40 | 360 | |
23d | — | 214 | 1.75 | 337.2/1.15 | 30.7 | 8877 | 40 | 360 | |
26a | — | 167 | 1.68 | 68.7/0.36 | 28.2 | 8279 | 10 | 360 | |
26b | — | 180 | 1.70 | 27.0/0.12 | 25.1 | 8063 | 30 | 360 | |
26c | 132 | 169 | 1.64 | 144.9/0.58 | 24.7 | 8021 | 10 | 360 | |
27a | — | 224 | 1.62 | –253.4/–1.21 | 24.4 | 7909 | 30 | 288 | |
27b | — | 266 | 1.68 | 7.8/0.03 | 24.2 | 7935 | 40 | 360 | |
27c | — | 131 | 1.68 | 115.2/0.46 | 25.7 | 8159 | 10 | 360 | |
31 | — | 129 | 1.80 | 194.8/0.78 | 33.8 | 8790 | 7 | 192 | |
36a | — | 141 | 1.78 | 85.4/0.36 | 33.0 | 8601 | >20 | 192 | |
36b | — | 166 | 1.80 | 135.5/0.54 | 34.1 | 8700 | >20 | 162 | |
36c | — | 161 | 1.72 | 43.8/0.16 | 28.7 | 8256 | >20 | 240 | |
36d | — | 140 | 1.71 | 231.4/0.78 | 30.1 | 8480 | >20 | 252 | |
TNTi | 81 | 290 | 1.65 | –55.5/–0.24 | 23.5 | 7459 | 15 | 353 | |
RDXi | 205 | 210 | 1.81 | 86.3/0.39 | 38.0 | 8983 | 7.5 | 120 | |
HMXi | 275 | 279 | 1.90 | 116.1/0.39 | 41.5 | 9221 | 7 | 112 | |
CL-20i | — | 215 | 2.03 | 365.4/0.83 | 46.7 | 9455 | 4 | 48 |
Entry | Starting material | Reagent | Yield/% |
---|---|---|---|
1 | LLM-116 | H2O2/H2SO4 | 93 |
2 | LLM-116 | H2S2O8 | 93 |
3 | LLM-116 | Oxone | 85 |
4 | ADNP | NaNO2/H2SO4 | 80 |
5 | ADNP | H2S2O8 | 37 |
6 | TIP | HNO3/SiO2/H2SO4 | 92 |
Entry | Starting material | Reagent | Yield/% |
---|---|---|---|
1 | LLM-116 | H2O2/H2SO4 | 93 |
2 | LLM-116 | H2S2O8 | 93 |
3 | LLM-116 | Oxone | 85 |
4 | ADNP | NaNO2/H2SO4 | 80 |
5 | ADNP | H2S2O8 | 37 |
6 | TIP | HNO3/SiO2/H2SO4 | 92 |
Compd. | Tma/℃ | Tdb/℃ | dc/(g?cm–3) | ΔfHd/(kJ?mol–1)/(kJ?g–1) | Pe/GPa | Df/(m?s–1) | ISg/J | FSh/N |
---|---|---|---|---|---|---|---|---|
39 | — | 262 | 1.88 | 274.7/0.79 | 34.6 | 8615 | >40 | — |
41a | — | 228 | 1.73 | 246.5/0.63 | 27.3 | 8041 | >40 | — |
41b | 249 | 272 | 1.67 | 506.4/1.26 | 27.1 | 8088 | >40 | — |
41c | 210 | 272 | 1.71 | 448.8/1.07 | 27.9 | 8201 | >40 | — |
41d | 212 | 266 | 1.72 | 558.0/1.29 | 29.0 | 8339 | >40 | — |
41e | — | 259 | 1.75 | 331.2/0.91 | 31.1 | 8330 | >40 | — |
41f | 247 | 297 | 1.82 | 557.0/1.26 | 31.0 | 8449 | >40 | — |
41g | 166 | 261 | 1.72 | 700.4/1.63 | 28.9 | 8231 | >40 | — |
41h | — | 260 | 1.80 | 428.1/1.19 | 32.8 | 8536 | >40 | — |
44a | 132 | 285 | 1.73 | 622.8/2.06 | 31.6 | 8621 | >40 | >360 |
44b | — | 215 | 1.76 | 709.9/2.23 | 34.4 | 8832 | 33 | 252 |
44c | — | 241 | 1.74 | 811.4/2.56 | 32.9 | 8798 | >40 | >360 |
44d | — | 340 | 1.78 | 624.1/1.81 | 31.1 | 8660 | >40 | >360 |
44e | — | 281 | 1.65 | 728.9/2.03 | 26.5 | 8236 | >40 | >360 |
44f | 233 | 262 | 1.70 | 831.7/2.22 | 28.9 | 8541 | 27 | 240 |
44g | — | 242 | 1.71 | 941.4/2.42 | 30.0 | 8685 | 20 | 216 |
44h | — | 279 | 1.72 | 828.3/2.16 | 28.0 | 8363 | >40 | 252 |
44i | — | 222 | 1.80 | 1211.7/3.15 | 35.2 | 9031 | 12 | 252 |
44j | — | 292 | 1.74 | 944.8/2.37 | 29.5 | 8555 | >40 | >360 |
44k | — | 303 | 1.77 | 1166.1/2.65 | 30.5 | 8647 | 20 | >360 |
49a | 186 | 260 | 1.68 | 422.3/1.55 | 25.1 | 8153 | >40 | >360 |
49b | 192 | 200 | 1.65 | 573.8/2.00 | 25.6 | 8264 | >40 | >360 |
49c | 224 | 260 | 1.75 | 470.2/1.62 | 29.8 | 8592 | >40 | >360 |
52a | — | 156 | 1.64 | 793.0/2.66 | 25.8 | 8167 | >40 | >360 |
52b | — | 137 | 1.72 | 937.1/2.99 | 29.7 | 8640 | 28 | 240 |
52c | — | 151 | 1.76 | 834.3/2.66 | 32.2 | 8747 | 32 | >360 |
55a | — | 216 | 1.72 | 763.6/2.96 | 31.3 | 8745 | 40 | 360 |
55b | — | 171 | 1.84 | 805.8/2.94 | 38.3 | 9295 | 35 | 216 |
55c | — | 196 | 1.77 | 910.0/3.15 | 35.0 | 9162 | 10 | 160 |
55d | — | 257 | 1.74 | 729.1/2.43 | 29.6 | 8668 | 40 | 360 |
55e | 195 | 221 | 1.61 | 834.7/2.65 | 25.4 | 8229 | 37.5 | 252 |
55f | 178 | 216 | 1.70 | 935.9/2.83 | 29.3 | 8712 | 30 | 240 |
55g | 188 | 208 | 1.66 | 1049.2/3.04 | 28.6 | 8657 | 12.5 | 216 |
55h | — | 216 | 1.76 | 930.3/2.73 | 29.5 | 8649 | 40 | 324 |
55i | — | 239 | 1.74 | 1049.8/2.96 | 29.6 | 8701 | 35 | 360 |
55j | — | 270 | 1.72 | 1275.2/3.23 | 28.6 | 8562 | 40 | 360 |
Compd. | Tma/℃ | Tdb/℃ | dc/(g?cm–3) | ΔfHd/(kJ?mol–1)/(kJ?g–1) | Pe/GPa | Df/(m?s–1) | ISg/J | FSh/N |
56a | — | 229 | 1.75 | 547.1/2.25 | 28.9 | 8801 | 35 | 360 |
56b | — | 187 | 1.78 | 445.0/1.82 | 29.9 | 8818 | 32 | 360 |
56c | — | 251 | 1.70 | 399.1/1.75 | 24.9 | 8286 | 40 | >360 |
56d | — | 224 | 1.69 | 485.5/1.70 | 23.9 | 8244 | 40 | >360 |
56e | — | 287 | 1.72 | 337.7/1.03 | 23.6 | 8138 | 40 | >360 |
63a | — | 137 | 1.85 | 220.6/0.58 | 35.8 | 8851 | 8 | 240 |
63b | 94 | 155 | 1.77 | 220.9/0.56 | 31.5 | 8670 | 10 | 240 |
63c | — | 193 | 1.76 | 116.2/0.33 | 29.4 | 8343 | 10 | 240 |
63d | — | 196 | 1.70 | 353.3/0.76 | 25.2 | 8136 | 15 | 360 |
63e | 185 | 186 | 1.75 | 791.9/1.55 | 27.3 | 8306 | 16 | 360 |
63f | — | 206 | 1.76 | 565.4/1.10 | 26.5 | 8219 | 12 | 360 |
63g | 187 | 193 | 1.81 | 1359.4/2.64 | 34.2 | 8952 | 10 | 360 |
63h | — | 250 | 1.80 | 1269.7/2.04 | 28.9 | 8542 | 18 | 360 |
67a | — | 187 | 1.76 | 711.4/1.77 | 30.0 | 8680 | >40 | >360 |
67b | — | 171 | 1.79 | 842.0/1.92 | 33.6 | 9077 | >40 | >360 |
67c | — | 187 | 1.73 | 1062.4/2.46 | 30.2 | 8759 | >40 | >360 |
67d | — | 195 | 1.71 | 677.9/1.40 | 25.1 | 8193 | >40 | >360 |
67e | — | 191 | 1.71 | 1068.7/2.07 | 27.3 | 8502 | >40 | >360 |
67f | — | 208 | 1.75 | 1014.6/1.85 | 29.7 | 8705 | 22.4 | >360 |
67g | — | 169 | 1.72 | 1300.5/2.58 | 25.7 | 8117 | >40 | >360 |
67h | — | 176 | 1.72 | 1511.2/2.39 | 25.9 | 8143 | >40 | >360 |
67i | — | 190 | 1.74 | 1270.5/2.84 | 26.0 | 8159 | >40 | >360 |
70b | — | 209 | 1.71 | 432.7/1.44 | 24.3 | 8062 | 20 | 360 |
70c | — | 254 | 1.67 | 348.4/1.25 | 28.3 | 8431 | 5 | 360 |
70d | — | 197 | 1.69 | 425.1/1.44 | 31.0 | 8648 | 10 | 360 |
70f | — | 168 | 1.76 | 820.6/2.52 | 27.9 | 8441 | 2 | 192 |
70h | — | 240 | 1.73 | 298.0/0.71 | 18.8 | 7364 | 40 | >360 |
72a | — | 250 | 1.68 | 405.1/1.58 | 22.4 | 7714 | 8 | >360 |
74a | — | 218 | 1.75 | 390.9/1.30 | 27.2 | 8223 | 15 | >360 |
74b | 251 | 286 | 1.68 | –50.4/–0.17 | 23.0 | 7689 | 40 | >360 |
74c | — | 230 | 1.76 | 303.7/1.00 | 28.6 | 8271 | 10 | >360 |
74e | — | 240 | 1.66 | 740.7/1.75 | 21.6 | 7563 | 10 | >360 |
76a | — | 201 | 1.81 | 295.7/0.85 | 32.8 | 8673 | 2 | 216 |
79a | — | 225 | 1.77 | 291.0/1.07 | 28.6 | 8516 | 25 | 168 |
79b | 220 | 289 | 1.81 | 287.3/0.92 | 29.0 | 8257 | 18 | 160 |
79c | — | 174 | 1.82 | 1404.5/2.68 | 30.4 | 8641 | 25 | 240 |
79d | 240 | 254 | 1.81 | 153.0/0.35 | 26.4 | 8109 | 20 | 240 |
79e | — | 202 | 1.75 | –196.3/–0.42 | 23.8 | 7745 | 25 | 288 |
79f | — | 213 | 1.76 | 346.3/1.02 | 25.7 | 8228 | 50 | >360 |
79g | — | 261 | 1.81 | 1566.2/2.65 | 30.6 | 8952 | 50 | 360 |
80 | — | 315 | 2.15 | 45.7/0.11 | 31.1 | 8275 | 1.5 | 60 |
82a | — | 304 | 1.78 | 327.4/0.71 | 28.0 | 8391 | >40 | >360 |
82b | — | 195 | 1.79 | 535.4/1.09 | 29.5 | 8632 | >40 | 216 |
82c | — | 183 | 1.73 | 1013.5/1.84 | 29.6 | 8731 | 2 | 54 |
82d | — | 206 | 1.80 | 767.4/1.42 | 28.6 | 8461 | >40 | >360 |
82e | — | 257 | 1.81 | 329.1/0.87 | 32.2 | 8638 | 7.5 | >360 |
82f | — | 156 | 1.84 | 634.5/1.56 | 35.5 | 9038 | 4 | 192 |
82g | — | 244 | 1.70 | 1040.1/1.82 | 26.0 | 8224 | 37.5 | >360 |
TNTi | 81 | 290 | 1.65 | –55.5/–0.24 | 23.5 | 7459 | 15 | 353 |
RDXi | 205 | 210 | 1.81 | 86.3/0.39 | 38.0 | 8983 | 7.5 | 120 |
HMXi | 275 | 279 | 1.90 | 116.1/0.39 | 41.5 | 9221 | 7 | 112 |
CL-20i | — | 215 | 2.04 | 365.4/0.83 | 46.7 | 9455 | 4 | 48 |
Compd. | Tma/℃ | Tdb/℃ | dc/(g?cm–3) | ΔfHd/(kJ?mol–1)/(kJ?g–1) | Pe/GPa | Df/(m?s–1) | ISg/J | FSh/N |
---|---|---|---|---|---|---|---|---|
39 | — | 262 | 1.88 | 274.7/0.79 | 34.6 | 8615 | >40 | — |
41a | — | 228 | 1.73 | 246.5/0.63 | 27.3 | 8041 | >40 | — |
41b | 249 | 272 | 1.67 | 506.4/1.26 | 27.1 | 8088 | >40 | — |
41c | 210 | 272 | 1.71 | 448.8/1.07 | 27.9 | 8201 | >40 | — |
41d | 212 | 266 | 1.72 | 558.0/1.29 | 29.0 | 8339 | >40 | — |
41e | — | 259 | 1.75 | 331.2/0.91 | 31.1 | 8330 | >40 | — |
41f | 247 | 297 | 1.82 | 557.0/1.26 | 31.0 | 8449 | >40 | — |
41g | 166 | 261 | 1.72 | 700.4/1.63 | 28.9 | 8231 | >40 | — |
41h | — | 260 | 1.80 | 428.1/1.19 | 32.8 | 8536 | >40 | — |
44a | 132 | 285 | 1.73 | 622.8/2.06 | 31.6 | 8621 | >40 | >360 |
44b | — | 215 | 1.76 | 709.9/2.23 | 34.4 | 8832 | 33 | 252 |
44c | — | 241 | 1.74 | 811.4/2.56 | 32.9 | 8798 | >40 | >360 |
44d | — | 340 | 1.78 | 624.1/1.81 | 31.1 | 8660 | >40 | >360 |
44e | — | 281 | 1.65 | 728.9/2.03 | 26.5 | 8236 | >40 | >360 |
44f | 233 | 262 | 1.70 | 831.7/2.22 | 28.9 | 8541 | 27 | 240 |
44g | — | 242 | 1.71 | 941.4/2.42 | 30.0 | 8685 | 20 | 216 |
44h | — | 279 | 1.72 | 828.3/2.16 | 28.0 | 8363 | >40 | 252 |
44i | — | 222 | 1.80 | 1211.7/3.15 | 35.2 | 9031 | 12 | 252 |
44j | — | 292 | 1.74 | 944.8/2.37 | 29.5 | 8555 | >40 | >360 |
44k | — | 303 | 1.77 | 1166.1/2.65 | 30.5 | 8647 | 20 | >360 |
49a | 186 | 260 | 1.68 | 422.3/1.55 | 25.1 | 8153 | >40 | >360 |
49b | 192 | 200 | 1.65 | 573.8/2.00 | 25.6 | 8264 | >40 | >360 |
49c | 224 | 260 | 1.75 | 470.2/1.62 | 29.8 | 8592 | >40 | >360 |
52a | — | 156 | 1.64 | 793.0/2.66 | 25.8 | 8167 | >40 | >360 |
52b | — | 137 | 1.72 | 937.1/2.99 | 29.7 | 8640 | 28 | 240 |
52c | — | 151 | 1.76 | 834.3/2.66 | 32.2 | 8747 | 32 | >360 |
55a | — | 216 | 1.72 | 763.6/2.96 | 31.3 | 8745 | 40 | 360 |
55b | — | 171 | 1.84 | 805.8/2.94 | 38.3 | 9295 | 35 | 216 |
55c | — | 196 | 1.77 | 910.0/3.15 | 35.0 | 9162 | 10 | 160 |
55d | — | 257 | 1.74 | 729.1/2.43 | 29.6 | 8668 | 40 | 360 |
55e | 195 | 221 | 1.61 | 834.7/2.65 | 25.4 | 8229 | 37.5 | 252 |
55f | 178 | 216 | 1.70 | 935.9/2.83 | 29.3 | 8712 | 30 | 240 |
55g | 188 | 208 | 1.66 | 1049.2/3.04 | 28.6 | 8657 | 12.5 | 216 |
55h | — | 216 | 1.76 | 930.3/2.73 | 29.5 | 8649 | 40 | 324 |
55i | — | 239 | 1.74 | 1049.8/2.96 | 29.6 | 8701 | 35 | 360 |
55j | — | 270 | 1.72 | 1275.2/3.23 | 28.6 | 8562 | 40 | 360 |
Compd. | Tma/℃ | Tdb/℃ | dc/(g?cm–3) | ΔfHd/(kJ?mol–1)/(kJ?g–1) | Pe/GPa | Df/(m?s–1) | ISg/J | FSh/N |
56a | — | 229 | 1.75 | 547.1/2.25 | 28.9 | 8801 | 35 | 360 |
56b | — | 187 | 1.78 | 445.0/1.82 | 29.9 | 8818 | 32 | 360 |
56c | — | 251 | 1.70 | 399.1/1.75 | 24.9 | 8286 | 40 | >360 |
56d | — | 224 | 1.69 | 485.5/1.70 | 23.9 | 8244 | 40 | >360 |
56e | — | 287 | 1.72 | 337.7/1.03 | 23.6 | 8138 | 40 | >360 |
63a | — | 137 | 1.85 | 220.6/0.58 | 35.8 | 8851 | 8 | 240 |
63b | 94 | 155 | 1.77 | 220.9/0.56 | 31.5 | 8670 | 10 | 240 |
63c | — | 193 | 1.76 | 116.2/0.33 | 29.4 | 8343 | 10 | 240 |
63d | — | 196 | 1.70 | 353.3/0.76 | 25.2 | 8136 | 15 | 360 |
63e | 185 | 186 | 1.75 | 791.9/1.55 | 27.3 | 8306 | 16 | 360 |
63f | — | 206 | 1.76 | 565.4/1.10 | 26.5 | 8219 | 12 | 360 |
63g | 187 | 193 | 1.81 | 1359.4/2.64 | 34.2 | 8952 | 10 | 360 |
63h | — | 250 | 1.80 | 1269.7/2.04 | 28.9 | 8542 | 18 | 360 |
67a | — | 187 | 1.76 | 711.4/1.77 | 30.0 | 8680 | >40 | >360 |
67b | — | 171 | 1.79 | 842.0/1.92 | 33.6 | 9077 | >40 | >360 |
67c | — | 187 | 1.73 | 1062.4/2.46 | 30.2 | 8759 | >40 | >360 |
67d | — | 195 | 1.71 | 677.9/1.40 | 25.1 | 8193 | >40 | >360 |
67e | — | 191 | 1.71 | 1068.7/2.07 | 27.3 | 8502 | >40 | >360 |
67f | — | 208 | 1.75 | 1014.6/1.85 | 29.7 | 8705 | 22.4 | >360 |
67g | — | 169 | 1.72 | 1300.5/2.58 | 25.7 | 8117 | >40 | >360 |
67h | — | 176 | 1.72 | 1511.2/2.39 | 25.9 | 8143 | >40 | >360 |
67i | — | 190 | 1.74 | 1270.5/2.84 | 26.0 | 8159 | >40 | >360 |
70b | — | 209 | 1.71 | 432.7/1.44 | 24.3 | 8062 | 20 | 360 |
70c | — | 254 | 1.67 | 348.4/1.25 | 28.3 | 8431 | 5 | 360 |
70d | — | 197 | 1.69 | 425.1/1.44 | 31.0 | 8648 | 10 | 360 |
70f | — | 168 | 1.76 | 820.6/2.52 | 27.9 | 8441 | 2 | 192 |
70h | — | 240 | 1.73 | 298.0/0.71 | 18.8 | 7364 | 40 | >360 |
72a | — | 250 | 1.68 | 405.1/1.58 | 22.4 | 7714 | 8 | >360 |
74a | — | 218 | 1.75 | 390.9/1.30 | 27.2 | 8223 | 15 | >360 |
74b | 251 | 286 | 1.68 | –50.4/–0.17 | 23.0 | 7689 | 40 | >360 |
74c | — | 230 | 1.76 | 303.7/1.00 | 28.6 | 8271 | 10 | >360 |
74e | — | 240 | 1.66 | 740.7/1.75 | 21.6 | 7563 | 10 | >360 |
76a | — | 201 | 1.81 | 295.7/0.85 | 32.8 | 8673 | 2 | 216 |
79a | — | 225 | 1.77 | 291.0/1.07 | 28.6 | 8516 | 25 | 168 |
79b | 220 | 289 | 1.81 | 287.3/0.92 | 29.0 | 8257 | 18 | 160 |
79c | — | 174 | 1.82 | 1404.5/2.68 | 30.4 | 8641 | 25 | 240 |
79d | 240 | 254 | 1.81 | 153.0/0.35 | 26.4 | 8109 | 20 | 240 |
79e | — | 202 | 1.75 | –196.3/–0.42 | 23.8 | 7745 | 25 | 288 |
79f | — | 213 | 1.76 | 346.3/1.02 | 25.7 | 8228 | 50 | >360 |
79g | — | 261 | 1.81 | 1566.2/2.65 | 30.6 | 8952 | 50 | 360 |
80 | — | 315 | 2.15 | 45.7/0.11 | 31.1 | 8275 | 1.5 | 60 |
82a | — | 304 | 1.78 | 327.4/0.71 | 28.0 | 8391 | >40 | >360 |
82b | — | 195 | 1.79 | 535.4/1.09 | 29.5 | 8632 | >40 | 216 |
82c | — | 183 | 1.73 | 1013.5/1.84 | 29.6 | 8731 | 2 | 54 |
82d | — | 206 | 1.80 | 767.4/1.42 | 28.6 | 8461 | >40 | >360 |
82e | — | 257 | 1.81 | 329.1/0.87 | 32.2 | 8638 | 7.5 | >360 |
82f | — | 156 | 1.84 | 634.5/1.56 | 35.5 | 9038 | 4 | 192 |
82g | — | 244 | 1.70 | 1040.1/1.82 | 26.0 | 8224 | 37.5 | >360 |
TNTi | 81 | 290 | 1.65 | –55.5/–0.24 | 23.5 | 7459 | 15 | 353 |
RDXi | 205 | 210 | 1.81 | 86.3/0.39 | 38.0 | 8983 | 7.5 | 120 |
HMXi | 275 | 279 | 1.90 | 116.1/0.39 | 41.5 | 9221 | 7 | 112 |
CL-20i | — | 215 | 2.04 | 365.4/0.83 | 46.7 | 9455 | 4 | 48 |
Compd. | Tma/℃ | Tdb/℃ | dc/(g?cm–3) | ΔfHd/(kJ?mol–1)/(kJ?g–1) | Pe/GPa | Df/(m?s–1) | ISg/J | FSh/N |
---|---|---|---|---|---|---|---|---|
86a | 160 | 328 | 1.69 | 158.5/0.68 | 25.4 | 8212 | >40 | 360 |
86b | 174 | 327 | 1.82 | 274.2/1.04 | 35.4 | 9005 | 29 | 360 |
86c | — | 247 | 1.72 | 501.0/1.91 | 30.3 | 8860 | 16 | 160 |
86d | — | 287 | 1.71 | 481.9/1.62 | 24.5 | 8036 | >40 | 360 |
86e | — | 289 | 1.67 | 963.8/2.30 | 24.6 | 8230 | >40 | 360 |
86g | 318 | 324 | 1.68 | 173.3/0.55 | 22.5 | 7948 | >40 | 360 |
86h | 213 | 222 | 1.69 | 477.0/1.38 | 25.6 | 8400 | >40 | 360 |
86i | — | 209 | 1.71 | 679.6/1.80 | 28.0 | 8732 | >40 | 360 |
86j | 208 | 215 | 1.76 | 605.5/2.00 | 29.9 | 8814 | 12 | 80 |
86k | — | 238 | 1.79 | 505.6/1.32 | 27.9 | 8355 | 23 | 160 |
90a | — | 144 | 1.67 | 393.1/1.96 | 26.3 | 8341 | 15 | 120 |
90b | — | 112 | 1.76 | 439.4/2.02 | 31.9 | 8859 | 8 | 120 |
90c | — | 192 | 1.62 | 371.0/1.53 | 22.5 | 7911 | 40 | 360 |
90d | — | 181 | 1.64 | 485.3/1.88 | 24.3 | 8196 | 25 | 240 |
90e | — | 188 | 1.74 | 916.4/2.71 | 27.5 | 8519 | 15 | 160 |
93a | — | 170 | 1.88 | 531.2/1.38 | 41.3 | 9495 | 7 | 120 |
93b | — | 181 | 1.81 | 423.1/1.20 | 35.9 | 8977 | 10 | 120 |
93c | — | 174 | 1.85 | 738.9/1.93 | 39.5 | 9399 | 5 | 60 |
93d | — | 190 | 1.68 | 454.7/1.04 | 26.9 | 8295 | 35 | 360 |
93e | — | 141 | 1.70 | 1144.8/2.17 | 30.8 | 8884 | 10 | 80 |
93f | — | 153 | 1.71 | 692.9/1.49 | 29.3 | 8612 | 30 | 360 |
93g | — | 163 | 1.78 | 1683.3/3.25 | 36.0 | 9166 | 5 | 60 |
93h | — | 203 | 1.83 | 1599.5/2.56 | 33.1 | 8993 | 10 | 120 |
96a | — | 178 | 1.61 | 1062.2/2.65 | 26.0 | 8237 | 27.5 | 324 |
96b | — | 221 | 1.75 | 1223.0/3.07 | 31.3 | 9082 | 12 | 144 |
96c | — | 280 | 1.69 | 916.8/2.49 | 26.2 | 8404 | 19 | >360 |
96d | — | 299 | 1.62 | 926.9/2.05 | 22.4 | 8023 | >60 | >360 |
96e | — | 255 | 1.64 | 1143.3/2.37 | 24.9 | 8396 | 35 | >360 |
100a | — | 169 | 1.78 | 188.9/0.43 | 33.0 | 8677 | 3 | 90 |
100b | — | 187 | 1.86 | 288.8/0.61 | 37.3 | 9148 | 2 | 20 |
100c | — | 165 | 1.81 | 497.5/1.06 | 36.1 | 8984 | 5 | 60 |
TNTi | 81 | 290 | 1.65 | –55.5/–0.24 | 23.5 | 7459 | 15 | 353 |
RDXi | 205 | 210 | 1.81 | 86.3/0.39 | 38.0 | 8983 | 7.5 | 120 |
HMXi | 275 | 279 | 1.90 | 116.1/0.39 | 41.5 | 9221 | 7 | 112 |
CL-20i | — | 215 | 2.03 | 365.4/0.83 | 46.7 | 9455 | 4 | 48 |
Compd. | Tma/℃ | Tdb/℃ | dc/(g?cm–3) | ΔfHd/(kJ?mol–1)/(kJ?g–1) | Pe/GPa | Df/(m?s–1) | ISg/J | FSh/N |
---|---|---|---|---|---|---|---|---|
86a | 160 | 328 | 1.69 | 158.5/0.68 | 25.4 | 8212 | >40 | 360 |
86b | 174 | 327 | 1.82 | 274.2/1.04 | 35.4 | 9005 | 29 | 360 |
86c | — | 247 | 1.72 | 501.0/1.91 | 30.3 | 8860 | 16 | 160 |
86d | — | 287 | 1.71 | 481.9/1.62 | 24.5 | 8036 | >40 | 360 |
86e | — | 289 | 1.67 | 963.8/2.30 | 24.6 | 8230 | >40 | 360 |
86g | 318 | 324 | 1.68 | 173.3/0.55 | 22.5 | 7948 | >40 | 360 |
86h | 213 | 222 | 1.69 | 477.0/1.38 | 25.6 | 8400 | >40 | 360 |
86i | — | 209 | 1.71 | 679.6/1.80 | 28.0 | 8732 | >40 | 360 |
86j | 208 | 215 | 1.76 | 605.5/2.00 | 29.9 | 8814 | 12 | 80 |
86k | — | 238 | 1.79 | 505.6/1.32 | 27.9 | 8355 | 23 | 160 |
90a | — | 144 | 1.67 | 393.1/1.96 | 26.3 | 8341 | 15 | 120 |
90b | — | 112 | 1.76 | 439.4/2.02 | 31.9 | 8859 | 8 | 120 |
90c | — | 192 | 1.62 | 371.0/1.53 | 22.5 | 7911 | 40 | 360 |
90d | — | 181 | 1.64 | 485.3/1.88 | 24.3 | 8196 | 25 | 240 |
90e | — | 188 | 1.74 | 916.4/2.71 | 27.5 | 8519 | 15 | 160 |
93a | — | 170 | 1.88 | 531.2/1.38 | 41.3 | 9495 | 7 | 120 |
93b | — | 181 | 1.81 | 423.1/1.20 | 35.9 | 8977 | 10 | 120 |
93c | — | 174 | 1.85 | 738.9/1.93 | 39.5 | 9399 | 5 | 60 |
93d | — | 190 | 1.68 | 454.7/1.04 | 26.9 | 8295 | 35 | 360 |
93e | — | 141 | 1.70 | 1144.8/2.17 | 30.8 | 8884 | 10 | 80 |
93f | — | 153 | 1.71 | 692.9/1.49 | 29.3 | 8612 | 30 | 360 |
93g | — | 163 | 1.78 | 1683.3/3.25 | 36.0 | 9166 | 5 | 60 |
93h | — | 203 | 1.83 | 1599.5/2.56 | 33.1 | 8993 | 10 | 120 |
96a | — | 178 | 1.61 | 1062.2/2.65 | 26.0 | 8237 | 27.5 | 324 |
96b | — | 221 | 1.75 | 1223.0/3.07 | 31.3 | 9082 | 12 | 144 |
96c | — | 280 | 1.69 | 916.8/2.49 | 26.2 | 8404 | 19 | >360 |
96d | — | 299 | 1.62 | 926.9/2.05 | 22.4 | 8023 | >60 | >360 |
96e | — | 255 | 1.64 | 1143.3/2.37 | 24.9 | 8396 | 35 | >360 |
100a | — | 169 | 1.78 | 188.9/0.43 | 33.0 | 8677 | 3 | 90 |
100b | — | 187 | 1.86 | 288.8/0.61 | 37.3 | 9148 | 2 | 20 |
100c | — | 165 | 1.81 | 497.5/1.06 | 36.1 | 8984 | 5 | 60 |
TNTi | 81 | 290 | 1.65 | –55.5/–0.24 | 23.5 | 7459 | 15 | 353 |
RDXi | 205 | 210 | 1.81 | 86.3/0.39 | 38.0 | 8983 | 7.5 | 120 |
HMXi | 275 | 279 | 1.90 | 116.1/0.39 | 41.5 | 9221 | 7 | 112 |
CL-20i | — | 215 | 2.03 | 365.4/0.83 | 46.7 | 9455 | 4 | 48 |
[1] |
Yang, G.-C.; Li, X.-D. Chin. J. Energ. Mater. 2018, 26,1000. (in Chinese)
|
( 杨光成, 李小东, 含能材料, 2018, 26,1000.)
|
|
[2] |
Lu, M. Chin. J. Energ. Mater. 2018, 26,373. (in Chinese)
|
( 陆明, 含能材料, 2018, 26,373.)
|
|
[3] |
Huo, H.; Zhang, J.; Dong, J.; Zhai, L.; Guoy, T.; Wang, Z.; Bi, F.; Wang, B. RSC Adv. 2020, 10,11816.
|
[4] |
Fischer, N.; Fischer, D.; Klapötke, T.M.; Piercey, D.G.; Stierstorfer, J. J. Mater. Chem. 2012, 22,20418.
|
[5] |
Huang, X.-C.; Guo, T.; Liu, M.; Wang, Z.-J.; Qiu, S.-J.; Ge, Z.-X. Chin. J. Energ. Mater. 2015, 23,291. (in Chinese)
|
( 黄晓川, 郭涛, 刘敏, 王子俊, 邱少君, 葛忠学, 含能材料, 2015, 23,291.)
|
|
[6] |
Trache, D.; Klapötke, T.M.; Maiz, L.; Abd-Elghany, M..; DeLuca, L.T. Green Chem. 2017, 19,4711.
|
[7] |
Oommen, C.; Jain, S.R. J. Hazard. Mater. 1999, 67,253.
pmid: 10370180 |
[8] |
Jos, J.; Mathew, S. Crit. Rev. Solid State Mater. Sci. 2017, 42,470.
|
[9] |
Venkatachalam, S.; Santhosh, G.; Ninan, K.N. Propellants, Explos.,Pyrotech. 2004, 29,178.
|
[10] |
Schoyer, H.F. R.; Welland-Veltmans, W.H. M.; Louwers, J.; Korting, P. A., O.G.; Heijden, A. E., D.M.; Keizers, H.L. J.; Berg, R.P. J. Propul. Power 2002, 18,131.
|
[11] |
Freudenmann, D.; Ciezki, H.K. Propellants, Explos.,Pyrotech. 2019, 44,1084.
|
[12] |
Drake, G.; Hawkins, T.; Brand, A.; Hall, L.; Mckay, M. Propellants, Explos.,Pyrotech. 2003, 28,174.
|
[13] |
Singh, R.P.; Verma, R.D.; Shreeve, J.M. Angew. Chem., Int. Ed. 2006, 45,3584.
|
[14] |
Gao, H.; Shreeve, J.M. Chem. Rev. 2011, 111,7377.
|
[15] |
Gao, H.; Zhang, Q.; Shreeve, J.M. J. Mater. Chem. A 2020, 8,4193.
|
[16] |
He, P.; Zhang, J.G.; Yin, X.; Wu, J.T.; Wu, L.; Zhou, Z.N.; Zhang, T.L. Chem.-Eur. J. 2016, 22,7670.
|
[17] |
Zhang, Y.; Gao, H.; Joo, Y.H.; Shreeve, J.M. Angew Chem., Int. Ed. 2011, 50,9554.
|
[18] |
Zhou, Y.-F.; Wang, T.; Wang, Q.-X.; Gao, H.-X. Chin. J. Energ. Mater. 2018, 26,967. (in Chinese)
|
( 周奕霏, 汪涛, 王秋晓, 高海翔, 含能材料, 2018, 26,967.)
|
|
[19] |
Wang, R.; Xu, H.; Guo, Y.; Sa, R.; Shreeve, J.M. J. Am. Chem. Soc. 2010, 132,11904.
|
[20] |
Dippold, A.A.; Klapötke, T.M. J. Am. Chem. Soc. 2013, 135,9931.
|
[21] |
Chen, S.; Liu, Y.; Feng, Y.; Yang, X.; Zhang, Q. Chem. Commun. 2020, 56,1493.
|
[22] |
Yang, F.; Zhang, P.; Zhou, X.; Lin, Q.; Wang, P.; Lu, M. Cryst. Growth Des. 2020, 20,3737.
|
[23] |
Zhao, G.; Kumar, D.; Yin, P.; He, C.; Imler, G.H.; Parrish, D.A.; Shreeve, J.M. Org. Lett. 2019, 21,1073.
|
[24] |
Zhao, T.-X.; Li, L.; Dong, Z.; Zhang, Y.; Zhang, G.-Q.; Huang, M.; Li, H.-B. Chin. J. Org. Chem. 2014, 34,304. (in Chinese)
|
( 赵廷兴, 李磊, 董战, 张勇, 张光全, 黄明, 李鸿波, 有机化学, 2014, 34,304.)
|
|
[25] |
Fustero, S.; Sánchez-Roselló, M.; Barrio, P.; Simón-Fuentes, A. Chem. Rev. 2011, 111,6984.
|
[26] |
Zheng, K.; Iqbal, S.; Hernandez, P.; Park, H.; LoGrasso, P.V.; Feng, Y. J. Med. Chem. 2014, 57,10013.
|
[27] |
Urich, R.; Grimaldi, R.; Luksch, T.; Frearson, J.A.; Brenk, R.; Wyatt, P.G. J. Med. Chem. 2014, 57,75369.
|
[28] |
Lahm, G.P.; Cordova, D.; Barry, J.D. Bioorg. Med. Chem. 2009, 17,4127.
|
[29] |
Weston, C.E.; Richardson, R.D.; Haycock, P.R.; White, A.J. P.; Fuchter, M.J. J. Am. Chem. Soc. 2014, 136,11878.
pmid: 25099917 |
[30] |
Hervé, G.; Roussel, C.; Graindorge, H. Angew. Chem., Int. Ed. 2010, 49,3177.
|
[31] |
Tang, Y.; Kumar, D.; Shreeve, J.M. J. Am. Chem. Soc. 2017, 139,13684.
|
[32] |
Kumar, D.; He, C.; Mitchell, L.A.; Parrish, D.A.; Shreeve, J.M. J. Mater. Chem. A 2016, 4,9220.
|
[33] |
Yin, P.; Zhang, J.; He, C.; Parrish, D.A.; Shreeve, J.M. J. Mater. Chem. A. 2014, 2,3200.
|
[34] |
Huang, H.; Shi, Y.; Li, H.; Li, H.; Pang, A.; Yang, J. Org. Lett. 2020, 22,5866.
pmid: 32672468 |
[35] |
Drukenmüller, I.E.; Klapötke, T.M.; Morgenstern, Y.; Rusan, M.; Stierstorfer, J.; Z. Anorg. Allg. Chem. 2014, 640,2139.
|
[36] |
Jiang, T.; Zhang, X.-Y.; Jing, M.; Shu, Y.-J.; Wang, J. Chin. J. Energ. Mater. 2014, 222,654. (in Chinese)
|
( 蒋涛, 张晓玉, 景梅, 舒远杰, 王军, 含能材料, 2014, 222,654.)
|
|
[37] |
Zhao, X.X.; Qi, C.; Zhang, L.B. Molecules 2014, 19,896.
|
[38] |
Politzer, P.; Lane, P.; Murray, J.S. Mol. Phys. 2013, 112,719.
|
[39] |
Wu, J.-P.; Cao, D.-L.; Wang, J.-L.; Liu, Y.; Li, Y.-X. Chin. J. Energ. Mater. 2016, 24,1121. (in Chinese)
|
( 吴军鹏, 曹端林, 王建龙, 刘洋, 李永祥, 含能材料, 2016, 24,1121.)
|
|
[40] |
Wang, W.-J.; Li, H.; Pan, R.-M.; Zhu, W.-H. Chin. J. Org. Chem. 2019, 39,1362. (in Chinese)
|
( 王万军, 李欢, 潘仁明, 朱卫华, 有机化学, 2019, 39,1362.)
|
|
[41] |
Zhang, Y.Q.; Guo, Y.; Joo, Y.H. Chem.-Eur. J. 2010, 116,10778.
|
[42] |
Zhang, Y.Q.; Parrish, D.A.; Shreeve, J.M. J. Mater. Chem. 2012, 22,12659.
|
[43] |
Schmidt, R.D.; Lee, G.S.; Pagoria, P.F.; Mitchell, A.R. J. Heterocycl. Chem. 2001,38, 1227.
|
[44] |
Zhang, Y.Q.; Parrish, D.A.; Shreeve, J.M. Chem.-Eur. J. 2012, 18,987.
pmid: 22170699 |
[45] |
Yin, P.; Parrish, D.A.; Shreeve, J.M. J. Am. Chem. Soc. 2015, 1137,4778.
|
[46] |
Deng, M.-C.; Wang, Y.; Zhang, W.-Q.; Zhang, Q.-H. Chin. J. Energ. Mater. 2017, 25,646. (in Chinese)
|
( 邓沐聪, 王毅, 张文全, 张庆华, 含能材料, 2017, 25,646.)
|
|
[47] |
Yin, P.; Mitchell, L.A.; Parrish, D.A. Chem.-Asian J. 2017, 112,378.
|
[48] |
Bölter, M.F.; Klapötke, T.M.; Kustermann, T.; Lenz, T.; Stierstorfer, J. Eur. J. Inorg. Chem. 2018, 37,4125.
|
[49] |
Zhang, Y.Y.; Li, Y.N. Dalton Trans. 2019, 448,1524.
|
[50] |
Zhang, Y.Y.; Li, Y.N.; Yu, T.; Liu, Y.Z.; Chen, S.P.; Ge, Z.X.; Sun, C.H.; Pang, S.P. ACS Omega 2019, 44,19011.
|
[51] |
Lei, C.J.; Yang, H.W.; Cheng, G.B. Dalton Trans. 2020, 49,1660.
|
[52] |
Hervé, G.; Roussel, C.; Graindorge, H. Angew. Chem., Int. Ed. 2010, 122,3177.
|
[53] |
Dalinger, I.L.; Vatsadze, I.A.; Shkineva, T.K.; Popova, G.P.; Shevelev, S.A. Mendeleev Commun. 2010, 20,253.
|
[54] |
Ravi, P.; Tewari, S.P. Catal. Commun. 2012, 19,37.
|
[55] |
Ravi, P.; Gore, G.M.; Tewari, S.P.; Sikder, A, K. J. Heterocycl. Chem. 2013, 50,1322.
|
[56] |
Zhao, X.X.; Zhang, J.C.; Li, S.H.; Yang, Q.P.; Liu, Y.C.; Pang, S.P. Org. Process Res. Dev. 2014, 18,886.
|
[57] |
Ravi, P.; Gore, G.M.; Sikder, A.K.; Tewari, S.P. Synth. Commun. 2012, 42,3463.
|
[58] |
Bölter, M.F.; Harter, A.; Klapötke, T.M.; Stierstorfer, J. ChemPlusChem 2018, 83,804.
|
[59] |
Janssen, J. W., A.M.; Habraken, C.L. J. Org. Chem. 1971, 36,3081.
|
[60] |
Janssen, J. W., A.M.; Koeners, H.J.; Kruse, C.G.; Habraken, C.L. J. Org. Chem. 1973, 38,1777.
|
[61] |
Makosza, M.; Winiarski, J. Acc. Chem. Res. 1987, 20,282.
|
[62] |
Li, C.; Liang, L.X.; Wang, K.; Bian, C.M.; Zhang, J.; Zhou, Z.M. J. Mater. Chem. A 2014, 22,18097.
|
[63] |
Li, C.; Zhang, M.; Chen, Q.S.; Li, Y.Y.; Gao, H.Q.; Fu, W.; Zhou, Z.M. Dalton Trans. 2016, 445,17956.
|
[64] |
Kumar, D.; Imler, G.H.; Parrish, D.A.; Shreeve, J.M. Chem.-Eur. J. 2017, 23,7876.
|
[65] |
Fu, W.; Zhao, B.J.; Zhang, M.; Li, C.; Gao, H.Q.; Zhang, J.; Zhou, Z.M. J. Mater. Chem. A 2017, 5,5044.
|
[66] |
Tang, Y.X.; Ma, J.C.; Imler, G.H.; Parrish, D.A.; Shreeve, J.M. Dalton Trans. 2019, 48,14490.
pmid: 31528967 |
[67] |
Sheremetev, A.B.; Yudin, I.L.; Palysaeva, N.V.; Suponitsky, K. Y. J. Heterocycl. Chem. 2012, 49,394.
|
[68] |
Tang, Y.X.; He, C.L.; Imler, G.H.; Parrish, D.A.; Shreeve, J.M. J. Mater. Chem. A 2018, 6,5136.
|
[69] |
Xu, M.X.; Cheng, G.B.; Xiong, H.L.; Wang, B.H.; Ju, X.H.; Yang, H.W. New J. Chem. 2019, 43,11157.
|
[70] |
Benz, M.; Klapötke, T.M.; Stierstorfer, J. Z. Anorg. Allg. Chem. 2020, 646,1.
|
[71] |
Gospodinov, I.; Domasevitch, K.V.; Unger, C.C.; Klapötke, T.M. Cryst. Growth Des. 2020, 20,755.
|
[72] |
Ma, Q.; Zhang, G.J.; Li, J.; Zhang, Z.Q.; Lu, H.C.; Liao, L.Y.; Fan, G.J.; Nie, F. Chem. Eng. J. 2020, 379,1.
|
[73] |
Tang, Y.; He, C.; Mitchell, L.A.; Parrish, D.A.; Shreeve, J.M. Angew. Chem., Int. Ed. 2016, 55,5565.
|
[74] |
Zhang, M.; Fu, W.; Li, C.; Gao, H.Q.; Tang, L.W.; Zhou, Z.M. Eur. J. Inorg. Chem. 2017, 22,2883.
|
[75] |
Schulze, M.C.; Scott, B.L.; Chavez, D.E. J. Mater. Chem. A 2015, 3,17963.
|
[76] |
Klenov, M.S.; Guskov, A.A.; Anikin, O.V.; Churakov, A.M.; Strelenko, Y.A.; Fedyanin, I.V.; Lyssenko, K.A.; Tartakovsky, V.A. Angew. Chem., Int. Ed. 2016, 55,11472.
|
[77] |
Chavez, E.E.; Parrish, D.A.; Mitchell, L.; Imler, G.H. Angew. Chem., Int. Ed. 2017, 56,3575.
|
[78] |
Yin, P.; Zhang, J.; Imler, G.H.; Parrish, D.A.; Shreeve, J.M. Angew. Chem., Int. Ed. 2017, 56,8834.
|
[79] |
Zhang, J.; Yin, P.; Mitchell, L.A.; Parrish, D.A.; Shreeve, J.M. J. Mater. Chem. A 2016, 4,7430.
|
[80] |
Shevelev, S.A.; Dalinger, I.L.; Shkineva, T.K.; Gulevskaya, B. I., U. V. I.; Kanishichev, M.I. Russ. Chem. Bull. 1993. 42,1063.
|
[81] |
Zhang, J.H.; Parrish, D.A.; Shreeve, J.M. Chem.-Asian J. 2014, 99,2953.
|
[82] |
Yin, P.; He, C.L.; Shreeve, J.M. J. Mater. Chem. A 2016, 4,1514.
|
[83] |
Yin, P.; Zhang, J.H.; Mitchell, L.A.; Parrish, D.A.; Shreeve, J.M. Angew. Chem., Int. Ed. 2016, 555,12895.
|
[84] |
Li, Y.N.; Hu, J.J.; Chang, P.; Chen, T.; Zhang, H.W.; Wang, B. Chin. J. Expl. Propell. 2019, 42,341. (in Chinese)
|
( 李亚南, 胡建建, 常佩, 陈涛, 张红武, 王彬, 火炸药学报, 2019, 42,341.)
|
|
[85] |
Xia, H.L.; Zhang, W.Q.; Jin, Y.H. ACS Appl. Mater. Interfaces 2019, 111,45914.
|
[86] |
Zhang, W.Q.; Xia, H.L.; Yu, R.J.; Zhang, J.H.; Wang, K.C.; Zhang, Q.H. Propellants, Explos.,Pyrotech. 2020, 45,546.
|
[87] |
Luo, Y.-F.; Ge, Z.-X.; Wang, B.-Z.; Zhang, H.-H; Liu, X. Chin. J. Energ. Mater. 2007, 15,205. (in Chinese)
|
( 罗义芬, 葛忠学, 王伯周, 张海昊, 刘愆, 含能材料, 2007, 15,205.)
|
|
[88] |
Cameron, M.; Gowenlock, B.G.; Boyd, A.F. J. Chem. Soc.,Perkin Trans. 2 1996, 11,2271.
|
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