6236–6239; (d) Y.-H. Joo, B. Twamley and J. M. Shreeve,
€
C. M. Sabate and M. Rusan, Z. Anorg. Allg. Chem., 2008, 634,
1867–1874; (f) C.-M. Jin, C. Ye, C. Piekarski, B. Twamley and
J. M. Shreeve, Eur. J. Inorg. Chem., 2005, 3760–3767; (g)
Y. Gao, C. Ye, B. Twamley and J. M. Shreeve, Chem.–Eur. J.,
After stirring at ambient temperature for 3 h, the silver salt was
removed by filtering the solution three times, and the solvent was
removed under a stream of air. A 0.890 g portion (2.43 mmol,
98%) of colorless crystal 13 was obtained. Colorless crystal; mp
140 ꢀC, 213 ꢀC (dec.). ~n/cmꢁ1 3386, 3331, 3303, 3252, 3150, 3068,
1678, 1636, 1505, 1454, 1393, 1339, 1295, 1261, 1187, 1157, 1111,
1038, 978, 889, 801, 707, 591. dH (300 MHz; D2O) 4.97 (2 H, s,
CH2), 7.09 (4 H, br. s), 8.47 (4 H, br. s). dC (75.5 MHz; D2O) 49.0,
155.9, 159.8, 172.2. dH (300 MHz; DMSO[D6]) 4.53 (10 H, s, NH2
and CH2 overlap), 7.41 (4 H, s), 9.20 (4 H, s). dC (75.5 MHz;
DMSO[D6]) 49.3, 156.9, 160.3, 170.5. d14N (50.7 MHz; DMSO
[D6]) ꢁ14.5 (NO2). d15N (50.7 MHz; DMSO[D6]) ꢁ327.4, ꢁ311.6,
ꢁ287.0, ꢁ161.7, ꢁ155.9, ꢁ73.6, ꢁ18.9, ꢁ15.0 (NO2), 2.9. Found
C, 15.89; H, 4.85; N, 60.71. Calc. for C5H18N16O4: C, 16.39; H,
4.95; N, 61.18. Density: 1.498 g cmꢁ3, Impact sensitivity: >40 J.
Chem.–Eur. J., 2009, 15, 9097–9104; (e) T. M. Klapotke,
€
2006, 12, 9010–9018; (h) T. M. Klapotke and C. M. Sabate,
Chem. Mater., 2008, 20, 1750–1763; (i) T. M. Klapotke and
C. M. Sabate, Chem. Mater., 2008, 20, 3629–3627; (j)
€
T. M. Klapotke, C. M. Sabate and J. M. Welch, Z. Anorg. Allg.
Chem., 2008, 634, 857–866; (k) T. M. Klapotke, C. M. Sabate
€
and J. Stierstorfer, New J. Chem., 2009, 33, 136–147; (l)
€
T. M. Klapotke and C. M. Sabate, Dalton Trans., 2009, 1835–
1841; (m) C. M. Sabate, E. Jeanneau and J. Stierstorfer, Z.
Anorg. Allg. Chem., 2011, 637, 1490–1501.
3 J. A. Garrison and R. M. Herbst, J. Org. Chem., 1957, 22, 278–
283.
€
4 T. M. Klapotke in High Energy Density Materials (Ed.:
€
T. M. Klapotke), Springer, Berlin, 2007, p. 85.
5 R. Raap and J. Howard, Can. J. Chem., 1969, 47, 813–819.
6 F. Einberg, J. Org. Chem., 1970, 35, 3978–3980.
Bis(triaminoguanidinium) 4-(carboxylatomethyl)-5-
7 (a) G.-W. Yang, Q.-Y. Li, Y. Zhou, G.-Q. Gu, Y.-S. Ma and
R.-X. Yuan, Inorg. Chem. Commun., 2008, 11, 1239–1242; (b)
G.-W. Yang, Q.-Y. Li, Y. Zhou, G.-Q. Gu, Y.-S. Ma and
R.-X. Yuan, Inorg. Chim. Acta, 2009, 362, 1234–1238; (c)
V. Hartdegen, T. M. Klapotke and S. M. Sproll, Inorg. Chem.,
2009, 48, 9549–9556; (d) Q.-Y. Li, G.-W. Yang, X.-Y. Tang,
Y.-S. Ma, W. Yao, F. Zhou, J. Chen and H. Zhou, Cryst. Growth
Des., 2010, 10, 165–170.
nitroiminotetrazolate monohydrate (14$H2O)
To an aqueous solution of 700 mg (4.98 mmol) tri-
aminoguanidine hydrochloride in 10 mL of water was added 1.00
g (2.49 mmol) silver 4-(carboxylatomethyl)-5-nitroiminotetrazol-
1-ide (12). After stirring at ambient temperature for 3 h, the silver
salt was removed by filtering 3 times, and the solvent was
removed under air. A 0.880 g portion (2.22 mmol, 89%) of white
solid 14$H2O was obtained. White solid; mp 109 ꢀC (H2O),
8 F. D. Marsh, J. Org. Chem., 1972, 37, 2966–2969.
9 (a) Y.-H. Joo and J. M. Shreeve, Angew. Chem., Int. Ed., 2009, 48,
564–567; (b) Y.-H. Joo and J. M. Shreeve, Chem.–Eur. J., 2009, 15,
3198–3203; (c) Y.-H. Joo and J. M. Shreeve, Angew. Chem., Int.
Ed., 2010, 49, 7320–7323; (d) Y.-H. Joo and J. M. Shreeve, J. Am.
Chem. Soc., 2010, 132, 15081–15091.
10 H. H. Krause in Energetic Materials (Ed.: U. Teipel), VCH,
Weinheim, 2005, p. 1.
11 S. Bastea, L. E. Fried, K. R. Glaesemann, W. M. Howard,
P. C. Souers, P. A. Vitello, CHEETAH 5.0 User’s Manual,
Lawrence Livermore National Laboratory, 2007.
170 C (dec.). ~n/cmꢁ1 3625, 3351, 3294, 3264, 3215, 1683, 1611,
ꢀ
1504, 1443, 1377, 1327, 1293, 1244, 1131, 1103, 1038, 1009, 951,
913, 795, 678, 637, 558. dH (300 MHz; D2O) 4.99 (2 H, s, CH2),
8.55 (br. s). dC (75.5 MHz; D2O) 48.9, 155.8, 159.2, 172.1. d15N
(50.7 MHz; D2O) ꢁ323.6, ꢁ281.2, ꢁ154.1, ꢁ147.1, ꢁ73.3,
ꢁ13.6, ꢁ8.3, 3.7. Found C, 14.17; H, 5.41; N, 61.06. Calc. for
C5H22N18O5$H2O: C, 14.49; H, 5.35; N, 60.85.
12 A portion of 20 mg of energetic materials was subjected to a drop-
hammer test using a 5 or 10 kg weight.
The water of crystallization of 14$H2O could be removed by
heating under high vacuum at 60 ꢀC for 5 h.
13 Bruker 2010, APEX2 v2010.3–0, Bruker AXS Inc., Madison,
Wisconsin, USA.
14 Bruker 2009, SAINT v7.68A, Bruker AXS Inc., Madison, Wisconsin,
USA.
15 Bruker 2008, XPREP v2008/2, Bruker AXS Inc., Madison,
Wisconsin, USA.
16 Bruker 2008, SADABS v2008/1, Bruker AXS Inc., Madison,
Wisconsin, USA.
14. White solid; mp 170 C, 188 C (dec.). ~n/cmꢁ1 3348, 3322,
3212, 3003, 2954, 1686, 1615, 1505, 1458, 1384, 1340, 1300, 1256,
1204, 1133, 1112, 1036, 972, 893, 801, 682, 637, 611. dH
(300 MHz; DMSO[D6]) 4.47 (14 H, s, NH2 and CH2 overlap),
8.65 (6 H, br. s). dC (75.5 MHz; DMSO[D6]) 49.7, 156.9, 159.3,
169.0. Found C, 14.87; H, 5.14; N, 62.15. Calc. for C5H20N18O4:
C, 15.15; H, 5.09; N, 63.61. Density: 1.529 g cmꢁ3. Impact
sensitivity: >40 J.
ꢀ
ꢀ
17 Bruker 2008, SHELXTL v2008/4. Bruker AXS Inc., Madison,
Wisconsin, USA.
18 Gaussian 03, Revision D.01, M. J. Frisch, G. W. Trucks,
H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman,
J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant,
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C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev,
A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala,
K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg,
V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain,
O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari,
J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford,
J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz,
I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham,
C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill,
B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople,
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Acknowledgements
The authors gratefully acknowledge the support of the Office of
Naval Research (N00014-10-0097) and the Agency for Defense
Development (Korea).
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