Journal of Inorganic and General Chemistry
www.zaac.wiley-vch.de
ARTICLE
Zeitschrift für anorganische und allgemeine Chemie
1
362 (29), 1337 (22), 1317 (34), 1241 (28), 1202 (17), 1143 (37), 1110
41), 1004 (19), 966 (17), 923 (94), 895 (35), 838 (65), 751 (17), 685
29), 669 (24), 598 (27), 585 (32), 560 (31), 520 (27), 493 (28), 354
Acknowledgements
(
(
(
HSF is gratefully acknowledged for the award of a Ph.D. scholarship
to Q.J.A. Financial support of this work by the Ludwig-Maximilian
University of Munich (LMU), the U.S. Army Research Laboratory
–1
46), 333 (29), 259 (51), 222 (26) cm . MS (DEI+) m/e: 281.2 [[M +
+
H] ]. C
C 30.00, H 4.25, N 19.92%. DSC (5 °C min , onset): 188 °C (mp.),
02 °C (dec.). BAM drophammer: Ͼ40 J. Friction tester: Ͼ360 N
grain size 100–500 μm).
7 12 4 8
H N O (280.19): calcd. C 30.01, H 4.32, N 20.00%; found:
–1
(
(
ARL), the Armament Research, Development and Engineering Center
ARDEC), the Office of Naval Research (ONR) under Grant No.
2
(
ONR.N00014-12-1-0538, and the Bundeswehr – Wehrtechnische
Dienststelle für Waffen und Munition (WTD 91) under Grant No.
E/E91S/FC015/CF049 is gratefully acknowledged. We acknowledge
collaborations with Dr. Mila Krupka (OZM Research, Czech Republic)
in the development of new testing and evaluation methods for ener-
getic materials and with Dr. Muhamed Suceska (Brodarski Institute,
Croatia) in the development of new computational codes to predict
the detonation and propulsion parameters of novel explosives. We are
indebted to and thank Drs. Betsy M. Rice, Jesse Sabatini, and Brad
Forch (ARL, Aberdeen, Proving Ground, MD) for many inspired dis-
cussions.
1
Nitroisobutylglycerol tris(nitrocarbamate) (3c): H NMR ([D
6
]ace-
) ppm. 1 C{ H} NMR
2
3
1
tone): δ = 13.7 (br., 3 H, NH), 4.88 (s, 6 H, CH
[D ]acetone): δ = 147.2 (CO), 88.2 (CNO ), 62.6 (CH
NMR ([D ]acetone): δ = –8 (CNO ), –46 (NHNO ) ppm. IR (ATR):
ν˜ = 3247 (w), 3197 (w), 3053 (w), 2360 (w), 1772 (s), 1614 (s), 1571
w), 1553 (m), 1445 (m), 1387 (w), 1355 (w), 1329 (m), 1198 (s),
174 (s), 1012 (w), 979 (m), 955 (m), 861 (w), 819 (w), 801 (w), 747
1
4
(
6
2
2
) ppm.
N
6
2
2
(
1
–1
(w), 718 (w) cm . Raman (1064 nm, 500 mW): ν˜ = 3198 (9), 3022
(18), 2983 (32), 2918 (10), 2708 (7), 1774 (43), 1619 (16), 1573 (10),
1555 (12), 1468 (33), 1357 (28), 1323 (42), 1268 (14), 1207 (14), 1180
(
6
11), 1101 (12), 1031 (100), 981 (20), 862 (35), 816 (11), 732 (12),
–1
References
47 (16), 464 (35), 350 (29), 234 (27) cm . MS (DCI+) m/e: 416.2
+
[
[M + H] ]. C
found: C 20.34, H 2.33, N 23.92%. DSC (5 °C min , onset): 149 °C
dec.). BAM drophammer: 15 J. Friction tester: 360 N (grain size
Ͻ100 μm).
7
H
9
N
7
O
14 (415.18): calcd. C 20.25, H 2.18, N 23.62%;
[1] J. Thiele, A. Lachman, Justus Liebigs Ann. Chem. 1895, 288,
–1
267–311.
[
2] a) Q. J. Axthammer, B. Krumm, T. M. Klapötke, J. Org. Chem.
015, 80, 6329–6335; b) Q. J. Axthammer, B. Krumm, T. M.
(
2
Klapötke, Eur. J. Org. Chem. 2015, 2015, 723–729; c) Q. J. Axt-
hammer, T. M. Klapötke, B. Krumm, Chem. Asian J.
DOI: 10.1002/asia.201501241.
1
But-2-yne-1,4-diyl dicarbamate (2d): H NMR ([D
6
]DMSO): δ = 6.7
) ppm. 13C{ H} NMR ([D
1
[3] J. Köhler, R. Meyer, A. Homburg, Explosivstoffe, Wiley-VCH,
Weinheim, Germany, 2008.
(br., 4 H, NH
2
), 4.61 (s, 4 H, CH
2
6
]DMSO): δ
156.3 (CO), 82.0 (Csp), 51.8 (CH ]DMSO): δ =
) ppm. 14N NMR ([D
302 (NH ) ppm. IR (ATR): ν˜ = 3445 (m), 3333 (w), 3251 (m), 3188
=
–
(
(
6
(
1
(
(
2
6
[
4] A. R. Modarresi-Alam, F. Khamooshi, M. Nasrollahzadeh, H. A.
Amirazizi, Tetrahedron 2007, 63, 8723–8726.
2
w), 2954 (w), 1722 (s), 1601 (m), 1445 (m), 1406 (m), 1319 (s), 1225
[
[
5] M. G. Kim, J. Appl. Polym. Sci. 2011, 122, 2209–2220.
6] a) R. Graf, Chem. Ber. 1956, 89, 1071–1079; b) D. N. Dhar,
K. S. K. Murthy, Synthesis 1986, 1986, 437–449.
m), 1154 (m), 1121 (m), 1039 (s), 1003 (m), 927 (m), 773 (s), 723 (m),
–1
86 (w) cm . Raman (1064 nm, 500 mW): ν˜ = 3446 (3), 3247 (6), 3184
6), 2980 (31), 2955 (100), 2903 (7), 2879 (9), 2327 (36), 2254 (79),
714 (18), 1608 (13), 1454 (45), 1402 (22), 1335 (19), 1234 (24), 1136
20), 1053 (20), 990 (13), 933 (37), 832 (15), 643 (33), 561 (38), 432
[7] Q. J. Axthammer, T. M. Klapötke, B. Krumm, R. Moll, S. F. Rest,
Z. Anorg. Allg. Chem. 2014, 640, 76–83.
[8] a) G. Gattow, W. K. Knoth, Z. Anorg. Allg. Chem. 1983, 499,
194–204; b) D. S. Bohle, Z. Chua, Inorg. Chem. 2014, 53, 11160–
–1
+
26), 355 (73), 249 (18) cm . MS (DEI+) m/e: 173.1 [[M + H] ].
(172.14): calcd C 41.86, H 4.68, N 16.27%; found: C 41.69,
11172.
6 8 2 4
C H N O
–1
[9] a) T. Urbanski, W. Tarantowicz, Bull. Acad. Pol. Sci. Ser. Sci.
Chim. Geol. Geogr. 1958, 6, 289–292; b) A. D. Nikolaeva, A. P.
Kirsanov SU504749A1 1976; c) S. Narasimhan, S. K. Srinivasan,
N. Venkatasubramanian, Magn. Reson. Chem. 1987, 25, 91–92.
H 4.67, N 16.49%. DSC (5 °C·min , onset): 187 °C (melt.), 264 °C
dec.). BAM drophammer: Ͼ40 J. Friction tester: Ͼ360 N (grain size
(
Ͻ100 μm).
[
10] T. M. Klapötke, Chemistry of High-Energy Materials, 2nd ed.,
de Gruyter, Berlin, 2012.
But-2-yne-1,4-diyl bis(nitrocarbamate) (3d): 1H NMR ([D
]ace-
6
[
[
[
11] M. Su c´ eska, EXPLO5 V.6.02, Zagreb (Croatia), 2013.
12] M. Göbel, T. M. Klapötke, Adv. Funct. Mater. 2009, 19, 347–365.
13] A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Gia-
covazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R.
Spagna, J. Appl. Crystallogr. 1999, 32, 115–119.
) ppm. 13C{ H} NMR
1
tone): δ = 13.5 (br., 2 H, NH), 4.95 (s, 4 H, CH
2
(
(
(
[D
6
]acetone): δ = 147.9 (CO), 81.0 (Csp), 53.9 (CH
]acetone): δ = –46 (NO ), –199 (NH) ppm. IR (ATR): ν˜ = 3168
) ppm. 14N NMR
2
[D
6
2
w), 3048 (w), 1737 (m), 1606 (m), 1442 (m), 1374 (m), 1319 (m),
235 (m), 1189 (s), 1159 (s), 1011 (m), 995 (w), 936 (s), 816 (m), 754
1
[14] a) G. M. Sheldrick, SHELX-97, Programs for Crystal Structure
Determination, 1997; b) G. M. Sheldrick, Acta Crystallogr., Sect.
A 2008, 64, 112–122.
–1
(w), 731 (w), 662 (w) cm . Raman (1064 nm, 500 mW): ν˜ = 3173
(5), 2998 (20), 2967 (71), 2885 (7), 2336 (21), 2271 (25), 2258 (30),
[
[
[
15] L. Farrugia, J. Appl. Crystallogr. 1999, 32, 837–838.
1738 (20), 1628 (15), 1458 (14), 1442 (10), 1375 (38), 1329 (42), 1239
16] A. Spek, Acta Crystallogr., Sect. D 2009, 65, 148–155.
17] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A.
Robb, J. R. Cheeseman, V. B. G. Scalmani, B. Mennucci, G. A.
Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F.
Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M.
Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Naka-
jima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. J. A. Montgom-
ery, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers,
K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K.
Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi,
M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B.
Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E.
(
(
8), 1196 (21), 1013 (100), 992 (14), 949 (10), 935 (12), 783 (10), 532
–1
12), 467 (26), 346 (41), 287 (5) cm . MS (DEI+) m/e: 263.1 [[M +
+
6 6 4 8
H] ]. C H N O (262.13): calcd. C 27.49, H 2.31, N 21.37%; found:
C 27.42, H 2.42, N 21.19%. DSC (5 °C·min , onset): 148 °C (dec.).
–1
BAM drophammer: 8 J. Friction tester: 240 N (grain size 100–
500 μm).
Supporting Information (see footnote on the first page of this article):
Selected bond lengths, angles, torsion angles, information on hydrogen
bonds for the compounds 2a, 3a–d are available.
Z. Anorg. Allg. Chem. 2016, 211–218
217
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