Energetic materials containing fluorine. Design, synthesis and testing of furazan-containing energetic materials bearing a pentafluorosulfanyl group

Journal of Fluorine Chemistry

Volumn 143, Issue , 2012, Pages 112-122

  Martinez, Henry ^a   Zheng, Zhaoyun ^a   Dolbier Jr , William R ^a  

^a University of Florida ^*  (United States)

Author keywords

Basicity; Energetic materials; Furazan; Nucleophilicity; Pentafluorosulfanyl group

Indexed keywords

EID: 84867404900     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2012.03.010     Document Type: Article

References (46)

1. J.P. Agrawal, and R. Hodgson Organic Chemistry of Explosives 2007 John Wiley & Sons West Sussex
2. L.E. Fried, R. Manaa, P.F. Pagoria, and R.L. Simpson Annu. Rev. Mater. Res. 31 2001 291
3. L. Kazandjian, and J. Danel Propellants Explos. Pyrotech. 31 2006 20 24
4. J.P. Agrawal Prog. Energy Combust. Sci. 24 1998 1
5. C. Ye, G.L. Gard, R.W. Winter, R.G. Syvret, B. Twamley, and J.M. Shreeve Org. Lett. 9 2007 3841 3844
6. M.E. Sitzmann, W.H. Gilligan, D.L. Ornellas, and J.S. Thrasher J. Energetic Mater. 8 1990 352 374
7. M.E. Sitzmann J. Fluorine Chem. 52 1991 195 207
8. H. Gao, C. Ye, R.W. Winter, G.L. Gard, M.E. Sitzmann, and J.M. Shreeve Eur. J. Inorg. Chem. 2006 3221
9. D.L. Ornellas Propellants Explos. Pyrotech. 14 1989 122 123
10. A.B. Sheremetiv, V.O. Kulagina, N.S. Aleksandrova, D.E. Dmitriev, and Y.A. Strelenko Propellants Explos. Pyrotech. 23 1998 142
11. P.F. Pagoria, G.S. Lee, A.R. Mitchell, and R.D. Schmidt Thermochim. Acta 384 2002 187 204
12. C. Zhang J. Mol. Struct. (Theochem.) 2006 77
13. I. Kohsari, S.M. Pourmortazaavi, and S.S. Hajimirsadeghi J. Therm. Anal. Calorim. 89 2007 543
14. A.B. Sheremetev, and N.S. Aleksandrova Russ. Chem. Bull. 54 2005 1715
15. M.B. Talawar, R. Sivabalan, N. Senthilkumar, G. Prabhu, and S.N. Asthana J. Hazard. Mater. 113 2004 11
16. D. Chavez, L. Hill, M. Hiskey, and S. Kinkead J. Energetic Mater. 18 2000 219
17. C.H. Lim, T.K. Kim, K.H. Kim, K.H. Chung, and J.S. Kim Bull. Kor. Chem. Soc. 31 2010 1400
18. M.B. Talawar, J.K. Nair, S.M. Pundalik, R.S. Satput, and S. Venugopalan J. Hazard. Mater. 136 2006 978
19. R.W. Beal, and T.B. Brill Propellants Explos. Pyrotech. 25 2000 241
20. M.D. Coburn J. Heterocycl. Chem. 5 1968 83
21. T.B. Brill, and G.K. Williams Combust. Flame 114 1998 569
22. V.P. Sinditskii, A.B. Sheremetev, and N.S. Aleksandrova Thermochim. Acta 473 2008 25
23. V.G. Kiselev, and N.P. Gritsan J. Phys. Chem. A 113 2009 3677
24. A.I. Lesnikovich, O.A. Ivanshkevich, S.V. Levchilk, A.I. Balabanovich, P.N. Gaponik, and A.A. Kulak Thermochim. Acta 388 2002 233
25. A.A. Paletsky, N.V. Budachev, and O.P. Korobeinichev Kinet. Catal. 50 2009 627
26. G. Silva, and J. Bozzelli J. Org. Chem. 73 2008 1343
27. K.W. Paul, M.M. Hurley, and K.K. Irikura J. Phys. Chem. A 113 2009 2483
28. V.G. Adndrianov, and A.V. Eremeev Chem. Heterocycl. Compd. 30 1994 608
29. R. Wang, Y. Guo, Z. Zeng, B. Twamley, and J.M. Shreeve Chem. Eur. J. 15 2009 2625
30. S. Garg, and J.M. Shreeve J. Mater. Chem. 21 2011 4787
31. A.B. Sheremetev, N.N. Makhova, and W. Friedrichsen Adv. Heterocycl. Chem. 78 2001 65 188
32. I.V. Tselinsky, S.F. Mel'nikova, and S.N. Vergisov Chem. Heterocycl. Compd. 17 1981 228
33. W.R. Dolbier Jr., S. Ait-Mohand, T.D. Schertz, T.A. Sergeeva, J.A. Cradlebaugh, A. Mitani, G.L. Gard, R.W. Winter, and J.S. Thrasher J. Fluorine Chem. 127 2006 1302 1310
34. S.M. Putis, V.Y. Zubarev, V.S. Poplavskii, and V.A. Ostrovskii Chem. Heterocycl. Compd. 40 2004 854
35. M.E. Sitzmann J. Fluorine Chem. 70 1995 31 38
36. A.R. Katritzky, Y. Zhang, and S.K. Singh Synthesis 2003 2795
37. K.C. Nicolaou, Y.-L. Zhong, P.S. Baran, J. Jung, H.-S. Choi, and W.H. Yoon J. Am. Chem. Soc. 124 2002 2202 2211
38. A.F. Clifford, and A. Shanzer J. Fluorine Chem. 7 1976 65 76
39. J.S. Thrasher, J.L. Howell, and A.F. Clifford Chem. Ber. 117 1984 1707
40. M.E. Sitzmann, W.H. Gilligan, US Patent 4,231,186 (1989).
41. M. Kol, and S. Rozen Chem. Commun. 1991 567 568
42. S. Rozen, and M. Kol J. Org. Chem. 57 1992 7342 7344
43. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J. 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, and J.A. Pople Gaussian 03, Revision E.01 2004 Gaussian, Inc. Wallingford, CT
44. S.W. Benson Thermochemical Kinetics 1976 John Wiley and Sons New York
45. C. Ye, and J.M. Shreeve Chem. Eng. Data 53 2008 520 524
46. M.J. Kamlet, and S.J. Jacobs J. Chem. Phys. 48 1968 23 35