J. M. Shreeve et al.
2058C (decomp); IR (KBr): n˜ =3464, 3330, 3206, 1690, 1605, 1456, 1306,
1132, 994, 762, 643 cmꢀ1 1H NMR: d=8.57 (s, 6H), 4.49 (s, 12H) ppm;
;
[2] a) H. Gao, Y. Huang, B. Twamley, C. Ye, J. M. Shreeve, ChemSus
h) H. Gao, C. Ye, O. D. Gupta, J.-C. Xiao, M. A. Hiskey, B. Twam-
13C NMR: d=169.7, 160.4, 135.2 ppm; elemental analysis (%) calcd for
C8H18N14O8 (MW=438.32): C 21.92, H 4.14, N 44.74; found: C 21.55, H
4.21, N 44.26.
Biguanidinium nitranilate monohydrate (9): Compound 9 was synthe-
sized by the same method as for 5 using 1.0 equivalent of biguanidinium
sulfate. Reddish-orange crystalline needles, yield 86%, 1=1.825 gcmꢀ3
,
m.p. 1788C, Td =2658C; IR (KBr): n˜ =3462, 3333, 3157, 2689, 1734, 1664,
1
1592, 1516, 1458, 1287, 1022, 778 cmꢀ1; H NMR: d=8.09 (s, 4H), 4.33 (s,
4H) ppm; 13C NMR: d=168.8, 157.2, 134.2 ppm; elemental analysis (%)
calcd for C8H11N7O9 (MW=349.21): C 27.51, H 3.17, N 28.08; found: C
27.34, H 3.09, N 27.74.
Aminocarbonylguanidinium nitranilate monohydrate (10): Compound 10
was synthesized by the same method as for 5 using 1.0 equivalent of
A
ACHTUNGTRENNUNGcarbonylguanidinium chloride. Orange solid, yield 82%, 1=
1736, 1695, 1587, 1456, 1335, 1251, 1024, 929, 766 cmꢀ1 1H NMR: d=
;
10.28 (s, 2H), 8.17 (s, 8H), 7.21 (s, 4H) ppm; 13C NMR: d=169.6, 156.9,
155.9, 134.4 ppm; elemental analysis (%) calcd for C10H16N10O11 (MW=
452.29): C 26.56, H 3.57, N 30.97; found: C 26.80, H 3.27, N 31.86.
b) T. M. Klapçtke, J. Stierstorfer, A. U. Wallek, Chem. Mater. 2008,
20, 4519–4530; c) T. M. Klapçtke, P. Mayer, C. M. Sabate, J. M.
Welch, N. Wiegand, Inorg. Chem. 2008, 47, 6014–6027; d) T. M. Kla-
ghiosoff, T. M. Klapçtke, P. Mayer, C. M. Sabate, A. Penger, J. M.
Holl, K. Karaghiosoff, T. M. Klapçtke, K. Loehnwitz, P. Mayer, H.
Noeth, K. Polborn, C. J. Rohbogner, M. Suter, J. J. Weigand, Inorg.
Chem. 2005, 44, 4237–4253.
5-Aminotetrazolium nitranilate (11): Compound 11 was synthesized by
the same method as for 5 using 1.0 equivalent of 5-aminotetrazolium
chloride. Brown crystalline needles, yield 96%, 1=1.697 gcmꢀ3, m.p.
2168C (decomp); IR (KBr): n˜ =3335, 3173, 2986, 2833, 1696, 1626, 1586,
1452, 1312, 1256, 1026, 789 cmꢀ1
;
1H NMR: d=7.98 (s, 4H) ppm;
13C NMR: d=166.3, 156.8, 132.9 ppm; elemental analysis (%) calcd for
C8H8N12O8 (MW=400.22): C 24.01, H 2.01, N 42.00; found: C 23.64, H
1.99, N 41.16.
3,4,5-Triamino-1,2,4-triazolium nitranilate (12): Compound 12 was syn-
thesized by the same method as for 5 using 1.0 equivalent of guanizinium
[4] Fickett W, Davis W. C. Detonation. Berkeley: Univ. Calif. Press,
1979..
chloride. Orange crystals, yield 96%, 1=1.713 gcmꢀ3
,
m.p. 3028C
(decomp); IR (KBr): n˜ =3426, 3355, 3290, 3183, 3022, 1699, 1602, 1526,
[5] a) O. Exner, Collect. Czech. Chem. Commun. 1967, 32, 1–23; b) J.
Stine, Report DE81032016; Los Alamos National Laboratory: Los
260–278; f) S. Beaucamp, N. Marchet, D. Mathieu, V. Agafonov,
mann, Acta Crystallogr. Sect B 2002, 57, 489–493; h) H. R. Karfun-
1457, 1264, 1022, 802, 770 cmꢀ1 1H NMR: d=7.06 (s, 8H), 5.66 (s, 4H)
;
ppm; 13C NMR: d=169.7, 151.3, 134.8 ppm; elemental analysis (%) calcd
for C10H14N14O8 (MW=458.31): C 26.21, H 3.08, N 42.79; found: C 25.97,
H 2.96, N 42.24.
1-Methyl-4-amino-1,2,4-triazolium nitranilate (13): Compound 13 was
synthesized by the same method as for 5 using 1.0 equivalent of 1-
methyl-4-amino-1,2,4-triazolium iodide. Orange crystalline needles, yield
94%, 1=1.671 gcmꢀ3, m.p. 2178C (decomp); IR (KBr): n˜ =3435, 3275,
3150, 3113, 3047, 1627, 1562, 1434, 1287, 1254, 1174, 997, 764 cmꢀ1
;
1H NMR: d=10.19 (s, 2H), 9.16 (s, 2H), 7.05 (s, 4H), 4.04 (s, 6H) ppm;
13C NMR: d=169.8, 146.3, 144.4, 134.9, 40.2 ppm; elemental analysis (%)
calcd for C12H14N10O8 (MW=426.30): C 33.81, H 3.31, N 32.86; found: C
33.38, H 3.14, N 32.21.
ences therein.
1,2,4-Triazolium nitranilate (14): Compound 14 was synthesized by the
same method as for 5 using 1.0 equivalent of 1,2,4-triazolium chloride.
Red crystalline solid, yield 87%, 1=1.799 gcmꢀ3, m.p. 2698C (decomp);
IR (KBr): n˜ =3119, 2949, 2800, 1595, 1526, 1475, 1316, 1035, 947, 881,
[7] a) M. Tsuyoshi, M. Yasushi, Y. Yumi, F. Kozo, Y. Hideki, S. Gunzi,
N. Kazuhiro, J. Am. Chem. Soc. 2007, 129, 10837–10846; b) F. A.
[8] H. Bock, S. Nick, C. Nather, J. W. Bats, Z. Naturforsch. B: Chem.
Sci. 1994, 49, 1021–1030.
632 cmꢀ1 1H NMR: d=9.87 (s, 4H), 9.07 (s, 4H) ppm; 13C NMR: d=
;
167.5, 145.5, 133.5 ppm; elemental analysis (%) calcd for C10H8N8O8
(MW=368.22): C 32.62, H 2.19, N 30.43; found: C 32.66, H 2.06, N
29.81.
[9] a) M. K. Kabir, M. Kawahara, K. Adachi, S. Kawata, T. Ishii, S.
Kiaagawa, Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A 2002, 376,
65–70; b) C. Robl, Z. Naturforsch., B: Chem. Sci. 1987, 42, 972–
976; c) F. Tinti, M. Verdaguer, O. Kahn, J. M. Savariault, Inorg.
Anal. Chim. Acta, 1972, 58, 131–139.
[10] O. C. Dermer, V. H. Dermer, J. Am. Chem. Soc. 1939; 61, 3302–
3303.
Acknowledgements
[11] a) A. Hammerl, T. M. Klapçtke, H. Noth, M. Warchhold, G. Holl,
Hammerl, G. Holl, M. Kaiser, T. M. Klapçtke, H. Z. Piotrowski, Z.
Natl. Bur. Stand. 1970, 74 A, 309; d) M. Gobel, T. M. Klapçtke, Z.
Anorg. Allg. Chem. 2007, 633, 1006–1017; e) J. O. Thomas, R. Limi-
The authors gratefully acknowledge the support of DTRA (HDTRA1–
07–1–0024), NSF (CHE-0315275), and ONR (N00014–06–1–1032). The
Bruker (Siemens) SMART APEX diffraction facility was established at
the University of Idaho with the assistance of the NSF-EPSCoR program
and the M. J. Murdock Charitable Trust, Vancouver, WA.
922
ꢀ 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Chem. Eur. J. 2009, 15, 917 – 923