TMS) d/ppm: 3.12 (s, 9 H, –CH3), 3.49 (s, 6 H, –CH3);
13C{1H} NMR (DMSO-d6, 100.63 MHz, 25 1C, TMS)
d/ppm: 42.4 (3 C, CH3), 38.1 (2 C, CH3); Raman v˜/cmꢁ1 (rel.
int.): 291(13), 343(8), 384(4), 420(4), 495(3), 562(7), 777(9),
825(9), 916(3), 949(1), 966(4), 1106(5), 1145(3), 1251(5),
1304(3), 1364(6), 1396(21), 1427(11), 1444(9), 1475(37), 2730(2),
2762(1), 2791(5), 2840(11), 2945(92), 3008(100), 3018(86);
IR v˜/cmꢁ1 (golden gate, rel. int.): 3071(w) 3010(w) 2945(w)
2356(w) 2182(w) 2168(w) 2042(w) 1963(w) 1946(w) 1704(w)
1629(w) 1598(w) 1555(w) 1482(m) 1461(m) 1439(w) 1407(m)
1385(s) 1361(m) 1299(w) 1261(m) 1229(m) 1139(w) 1113(w)
1101(m) 1049(w) 968(m) 948(m) 908(m) 820(w) 775(m) 746(w)
707(w) 638(w) 589(s) 558(w) 497(w) 473(w) 463(w).
2007, 2025–2030; R. W. Wang, H. Gao, C. Ye, B. Twamley and
J. M. Shreeve, Inorg. Chem., 2007, 46, 932–938.
6 G. Kaplan, G. Drake, K. Tollison, L. Hall and T. Hawkins,
J. Heterocycl. Chem., 2005, 42, 19–27; H. Oestmark, Proceedings
of the 9th Seminar on New Trends in the Research of Energetic
Materials, Institute of Energetic Materials, University of
Pardubice, Czech Republic, April 19–21, 2006.
7 J. Uddin, V. Barone and G. E. Scuseria, Mol. Phys., 2006, 104,
745–749; H. Oestmark, S. Walin and P. Goede, Cent. Eur. J. Energ.
Mater., 2007, 4, 83–108.
8 H. Feuer and A. T. Nielsen, Nitro Compounds, Wiley-VCH,
Weinheim, Germany, 1990.
9 A. T. Nielsen, Nitrocarbons, Wiley-VCH, Weinheim, Germany, 1995.
10 D. E. Chavez, M. A. Hiskey and R. D. Gilardi, Angew. Chem., Int.
Ed., 2000, 39, 1861–1863.
11 A. Hammerl, T. M. Klapotke, H. Noth, M. Warchhold, G. Holl
¨
and M. Kaiser, Inorg. Chem., 2001, 40, 3570–3575.
¨
12 International Conference on Green Propellant for Space Propul-
sion, Noordwijk, The Netherlands, June 20–22, 2001; http://
esamultimedia.esa.int/conferences/01a05/index.html.
Acknowledgements
13 A. K. Sikder and N. Sikder, J. Hazard. Mater., 2004, A112, 1–15.
14 H. Gao, Y. Huang, C. Ye, B. Twamley and J. M. Shreeve,
Chem.–Eur. J., 2008, 14, 5596–5603.
Financial support by the Centre Nationale de la Recherche
´
Scientifique (CNRS), the Centre Nationale d’Etudes Spatiales
15 (a) T. M. Klapoetke, P. Mayer, A. Schulz and J. J. Weigand,
Propellants, Explos., Pyrotech., 2004, 29, 325; (b) J. Heppekausen,
(CNES), the Societe Nationale des Poudres et des Explosifs
´
(SNPE) and the University Claude Bernard of Lyon are
gratefully acknowledged.
T. M. Klapotke and S. M. Sproll, J. Org. Chem., 2009, 74,
¨
D. Blaser, Z. Naturforsch., B: Chem. Sci., 2002, 57, 365–376;
¨
2460–2466; (c) B. Porath, P. Rademacher, R. Bose and
¨
(d) B. Rose, D. Schollmeyer and H. Meier, Liebigs Ann./Recl.,
1997, 409–412.
16 B. Porath, R. Munzenberg, P. Heymans, P. Rademacher, R. Bose,
¨
references therein.
17 W. E. Bull, H. A. Seaton and L. F. Audrieth, J. Am. Chem. Soc.,
1958, 80, 2516–2518.
Notes and references
¨
D. Blaser and R. Latz, Eur. J. Org. Chem., 1998, 1431–1440 and
1 T. M. Klapotke, P. Mayer, C. Miro
´
Sabate
N. Wiegand, Inorg. Chem., 2008, 47(13), 6014–6027;
T. M. Klapotke, C. Miro Sabate and J. Stierstorfer, Z. Anorg.
Allg. Chem., 2008, 11, 1867–1874; M. von Denffer, T. M. Klapotke
´
, J. M. Welch and
¨
´
´
¨
¨
18 N. Wiberg, H. Bayer and H. Bachhuber, Angew. Chem., 1975,
87(6), 202–203; N. Wiberg, H. W. Haering and S. K. Vasisht,
Z. Naturforsch. B: Anorg. Chem. Org. Chem., 1979, 34(2), 356–357.
19 A. F. Holleman, E. Wiberg and N. Wiberg, Lehrbuch der
Anorganischen Chemie, Walter de Gruyter, Berlin, Germany,
101st edn, 1995.
20 F. O. Rice and C. J. Grelecki, J. Am. Chem. Soc., 1957, 79(11),
2679–2680.
21 R. A. Rowe and L. F. Audrieth, J. Am. Chem. Soc., 1956, 78(3),
563–564.
22 H. H. Sisler, M. A. Mathur, S. R. Jain and R. Greengard, Ind. Eng.
Chem. Prod. Res. Dev., 1981, 20, 181–185.
23 L. J. Madgzinski, K. S. Pillay, H. Richard and Y. L. Chow, Can. J.
Chem., 1978, 56, 1657–1667 and references therein.
24 W. McBride and H. W. Kruse, J. Am. Chem. Soc., 1957, 79(3),
572–577.
and C. Miro
T. M. Klapo
2009, 1825–1834; T. M. Klapotke and C. Miro
´
Sabate
´
, Z. Anorg. Allg. Chem., 2008, 634, 2575–2582;
Sabate and M. Rasp, Dalton Trans.,
Sabate, Dalton
Trans., 2009, 1835–1841; M. Ebespacher, T. M. Klapotke and
´
´
¨
tke, C. Miro
´
´
¨
¨
¨
C. Miro
´
Sabate
´
,
Helv. Chim. Acta, 2009, 92, 977–996;
Sabate and J. M. Welch, Eur. J. Inorg.
Chem., 2009, 769–776; M. Ebespacher, T. M. Klapotke and
T. M. Klapotke, C. Miro
´
´
¨
¨
¨
C. Miro Sabate, New J. Chem., 2009, 33, 517–527; H. Delalu,
´ ´
, Cent. Eur.
K. Karaghiosoff, T. M. Klapotke and C. Miro
´
Sabate
´
¨
J. Energ. Mater, 2010, 7(3), 115–129.
2 T. M. Klapotke, P. Mayer, A. Schulz and J. J. Weigand,
¨
Propellants, Explos., Pyrotech., 2004, 29, 325–332; D. L. Strout,
J. Phys. Chem. A, 2004, 108, 10911–10916; M. H. V. Huynh,
M. A. Hiskey, E. L. Hartline, D. P. Montoya and R. Gilardi,
Angew. Chem., 2004, 116, 5032–5036 (Angew. Chem., Int. Ed.,
2004, 43, 4924–4928); R. Haiges, S. Schneider, T. Schroer and
K. O. Christe, Angew. Chem., 2004, 116, 5027–5032 (Angew.
Chem., Int. Ed., 2004, 43, 4919–4924).
25 W. H. Urry, P. Szecsi and D. W. Moore, J. Am. Chem. Soc., 1964,
86(11), 2224–2229.
26 S. N. Singh and R. K. Prasad, J. Indian Chem. Soc., 1992, 69(10),
648–650.
3 R. P. Singh, R. D. Verma, D. T. Meshri and J. M. Shreeve, Angew.
Chem., 2006, 118, 3664–3682 (Angew. Chem., Int. Ed., 2006, 45,
27 W. R. McBride and H. W. Kruse, US Pat., 3 135 800, 1952.
28 Method A: hold temperature at 90 1C for 1 min, then heat at
2 1C minꢁ1 to 130 1C.
3584–3601); T. M. Klapotke, Structure and Bonding, Springer,
¨
Berlin/Heidelberg, Germany, 2007; G. Drake, US Pat., 6 509
473, 2003; V. A. Dulles and G. Drake, AFOSR Ionic Liquids
Workshop, Aberdeen, MD, 2003.
29 (a) T. M. Klapotke and C. Miro
´
Sabate
´
, Z. Anorg. Allg. Chem.,
¨
2008, 634, 1017–1024; (b) T. M. Klapotke and C. Miro
´
Sabate,
´
¨
4 T. Abe, Y.-H. Joo, G.-H. Tao and J. M. Shreeve, Chem.–Eur. J.,
2009, 15, 4102–4110; Y.-H. Joo and J. M. Shreeve, Eur. J. Org.
Chem., 2009, 3573–3578; G.-H. Tao, Y.-H. Joo, B. Twamley and
J. M. Shreeve, J. Mater. Chem., 2009, 19, 5850–5854; Y. Guo,
G.-H. Tao, Z. Zeng, H. Gao and J. M. Shreeve, Chem.–Eur. J.,
2010, 16, 3753–3762; G.-H. Tao, Y. Guo, D. A. Parrish and
J. M. Shreeve, J. Mater. Chem., 2010, 20, 2999–3005; Y.-H. Joo
and J. M. Shreeve, Angew. Chem., Int. Ed., 2010, 49, 7320–7323;
Y.-H. Joo and J. M. Shreeve, J. Am. Chem. Soc., 2010, 132,
15081–15090.
Eur. J. Inorg. Chem., 2008, 5350–5366.
30 (a) K. Karaghiosoff, T. M. Klapotke, P. Mayer, C. Miro
´
Sabate
A. Penger and J. M. Welch, Inorg. Chem., 2008, 47, 1007–1019;
(b) C. Darwich, T. M. Klapotke and C. Miro Sabate, Chem.–Eur. J.,
2008, 14, 5756–5771; (c) T. M. Klapotke, C. Miro Sabate, A. Penger,
´
,
¨
´
´
¨
´
´
¨
M. Rusan and J. M. Welch, Eur. J. Inorg. Chem., 2009,
880–896.
31 F. R. Benson, The High Nitrogen Compounds, Wiley, New York,
1984.
32 N. B. Colthup, L. H. Daly and S. E. Wiberley, Introduction to
Infrared and Raman Spectroscopy, Academic Press, Boston, USA,
1990.
33 N–N and NQN bond lengths from: International Tables for X-ray
Crystallography, Kluwer Academic Publishers, Dordrecht, 1992,
vol. C.
5 H. Gao, C. Ye, R. W. Winter, G. L. Gard, M. E. Sitzmann and
J. M. Shreeve, Eur. J. Inorg. Chem., 2006, 3221–3226; Y. Gao,
C. F. Ye, B. Twamley and J. M. Shreeve, Chem.–Eur. J., 2006, 12,
9010–9018; G. Gao, R. Wang, B. Twamley, M. A. Hiskey and
J. M. Shreeve, Chem. Commun., 2006, 4007–4009; Y. Huang,
H. Gao, B. Twamley and J. M. Shreeve, Eur. J. Inorg. Chem.,
c
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