4,4′-Bis(nitramino)azofurazan and its salts. Study of molecular and crystal structure based on X-ray and quantum chemical data

Russian Chemical Bulletin

Volumn 58, Issue 10, 2009, Pages 2129-2136

  Suponitsky, K Yu ^a   Lyssenko, K A ^a   Antipin, M Yu ^a   Aleksandrova, N S ^b   Sheremetev, A B ^b   Novikova, T S ^b  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^b N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

azofurazans; density; density functional theory; furazans; nitramines; quantum chemical calculations; single crystal X ray diffraction

Indexed keywords

EID: 77955753607     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11172-009-0291-0     Document Type: Article

References (56)

1. E. Yu. Orlova, Khimiya i tekhnologiya brizantnykh vzryvchatykh veshchestv [Chemistry and Technology of High Explosives], Khimiya, Leningrad, 1981 (in Russian).
2. Organic Energetic Compounds, Ed. P. L. Marinkas, Nova Science Publ. Inc., 1996.
3. Energeticheskie kondensirivannye sistemy. Kratkii Entsiklopedicheskii slovar' [Energetic Condensed Systems. Abridged Encyclopaedia], Ed. B. P. Zhukov, 2nd edition, Yanus-K, Moscow, 2000 (in Russian).
4. Yu. Shu B. L. Korsunskii G. M. Nazin 2004 Uspekhi Khimii 73 320
5. Russ. Chem. Rev. (Engl. Transl.), 2004, 73
6. S. V. Sysolyatin A. A. Lobanova Yu. T. Chernikova G. V. Sakovich 2005 Uspekhi Khimii 74 830
7. Russ. Chem. Rev. (Engl. Transl.), 2005, 74
8. T. M. Klapotke, in Structure and Bonding, Ed. D. M. P. Mingos, Springer-Verlag, Berlin-Heidelberg, 2007, vol. 125, pp. 85-121.
9. J. P. Agrawal, R. D. Hodgson, Organic Chemistry of Explosives, John Wiley and Sons, Ltd., 2007.
10. S. V. Sysolyatin G. V. Sakovich V. N. Surmachev 2007 Uspekhi Khimii 76 724
11. Russ. Chem. Rev. (Engl. Transl.), 2007, 76
12. A. L. Fridman V. P. Ivshin S. S. Novikov 1969 Uspekhi Khimii 38 1448 1:CAS:528:DyaF1MXltVWiurY%3D
13. Russ. Chem. Rev. (Engl. Transl.), 1969, 38, 640
14. A. B. Sheremetev 1997 Ross. Khim. Zh. (Zh. Ross. Khim. O-va im. D. I. Mendeleeva) 41 43 1:CAS:528:DyaK2sXltVans74%3D
15. Mendeleev. Chem. J. (Engl. Transl.), 1997, 41, 62
16. G. K. Williams T. B. Brill 1998 Combustion and Flame 114 569 10.1016/S0010-2180(97)00330-1 1:CAS:528:DyaK1cXjtlahurw%3D (Pubitemid 28243854)
17. V. A. Frolovskii, V. A. Petrosyan, Izv. Akad. Nauk, Ser. Khim., 1999, 1935
18. Russ. Chem. Bull. (Engl. Transl.), 1999, 48, 1911
19. A. B. Sheremetev, I. L. Yudin, N. N. Makhova, I. V. Ovchinnikov, D. B. Lempert, Proc. 33st Int. Annual Conference of ICT - Energetic Materials: Synthesis, Production, and Application (June 25-June 28, 2002, Karlsruhe, FRG), 128/1-12.
20. th Int. Annual Conference of ICT - Energetic Materials: Reactions of Propellants, Explosives and Pyrotechnics (June 24-June 27, 2003, Karlsruhe, FRG), 101/1-10.
21. S. D. Shaposhnikov T. V. Romanova N. P. Spiridonova S. F. Mel'nikova I. V. Tselinskii 2004 Zh. Organ. Khim. 40 922
22. Russ. J. Org. Chem. (Engl. Transl.), 2004, 40, 884
23. A. V. Sergievskii T. V. Romanova S. F. Mel'nikova I. V. Tselinskii 2005 Zh. Organ. Khim. 41 270
24. Russ. J. Org. Chem. (Engl. Transl.), 2005, 41, 261
25. A. B. Sheremetev E. A. Ivanova N. P. Spiridonova S. F. Mel'nikova I. V. Tselinsky K. Yu. Suponitsky M. Yu. Antipin 2005 J. Heterocycl. Chem. 42 1237 10.1002/jhet.5570420634 1:CAS:528:DC%2BD2MXhtVaksb3O
26. A. B. Sheremetev, N. S. Aleksandrova, Izv. Akad. Nauk, Ser. Khim., 2005, 1665
27. Russ. Chem. Bull., Int. Ed., 2005, 54, 1715
28. G. N. Nechiporenko, D. B. Lempert, S. I. Soglasnova, N. N. Makhova, A. B. Sheremetev, Energeticheskie kondensirivannye sistwmy. Materialy III Vserossiiskoi konferetsii [Energetic Condensed Systems. Proc. III All-Russian Conference] (Chernogolovka), Yanus-K, Moscow, 2006, p. 193-194 (in Russian).
29. S. D. Shaposhnikov, A. Yu. Perkatyi, A. S. Yankovsky, S. F. Melnikova, I. V. Tselinsky, New Trends in Research of Energetic Materials, Pardubice, Czech Republic, 2007, 316-321.
30. Y. Oyumi A. L. Rheingold T. B. Brill 1986 J. Phys. Chem. 90 4686 10.1021/j100410a046 1:CAS:528:DyaL28XltlehsLk%3D
31. C. K. Lowe-Ma J. W. Fischer R. L. Willer 1990 Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 46 1853 10.1107/S0108270189013739
32. R. L. Willer R. S. Day 1992 J. Heterocycl. Chem. 29 1835 10.1002/jhet.5570290726 1:CAS:528:DyaK3sXhvFWltr0%3D
33. G. D. Solodyuk M. D. Boldyrev B. V. Gidaspov V. D. Nikolaev 1981 Zh. Organ. Khim. 17 861 1:CAS:528:DyaL3MXkvVSrsbc%3D
34. Russ. J. Org. Chem. (Engl. Transl.), 1981, 17
35. SMART and SAINT, Release 5.0, Area Detector control and Integration Software, Bruker AXS, Analytical X-Ray Instruments, Madison, Wisconsin, USA, 1998.
36. G. M. Sheldrick, SADABS: A Program for Exploiting the Redundancy of Area-detector X-Ray Data, University of Göttingen, Göttingen, Germany, 1999.
37. G. M. Sheldrick, SHELXTL-97 Program for Solution and Refinement of Crystal Structure, Bruker AXS Inc., Madison, WI-53719, USA, 1997.
38. W. Klyne V. Prelog 1960 Experientia 16 521 10.1007/BF02158433 1:CAS:528:DyaF3MXht1aisbY%3D
39. A. B. Sheremetev E. V. Shatunova B. B. Averkiev D. E. Dmitriev V. A. Petukhov M. Yu. Antipin 2004 Heteroatom Chem. 15 131 10.1002/hc.10226 1:CAS:528:DC%2BD2cXisFGhsro%3D
40. F. H. Allen 2002 Acta Crystallogr. B58 380 1:CAS:528:DC%2BD38XktVOqu74%3D
41. R. W. Beal C. D. Incarvito B. J. Rhatigan A. L. Rheingold T. B. Brill 2000 Propellants Explos. Pyrotech. 25 277 10.1002/1521-4087(200012)25:6<277:: AID-PREP277>3.0.CO;2-P 1:CAS:528:DC%2BD3MXmtFaisA%3D%3D (Pubitemid 32136324)
42. B. B. Averkiev M. Yu. Antipin A. B. Sheremetev T. V. Timofeeva 2003 Acta Crystallogr., Sect. C C59 o383 10.1107/S0108270103009521 1:CAS:528: DC%2BD3sXlt1OhtL8%3D
43. A. S. Batsanov Yu. T. Struchkov 1985 Zh. Struktur. Khim. 26 65 1:CAS:528:DyaL2MXktVKhur0%3D
44. J. Struct. Chem. (Engl. Transl.), 1985, 26
45. A. R. Katritzky B. Wallis R. T. C. Brownlee R. D. Topsom 1965 Tetrahedron 21 1681 10.1016/S0040-4020(01)98638-7 1:CAS:528:DyaF2MXks1ejtr8%3D
46. A. B. Sheremetev Yu. A. Strelenko T. S. Novikova L. I. Khmelnitskii 1993 Tetrahedron 49 5905 10.1016/S0040-4020(01)87956-4 1:CAS:528:DyaK2cXosFSg
47. A. B. Sheremetev N. N. Makhova W. Friedrichsen 2001 Adv. Heterocycl. Chem. 78 65 10.1016/S0065-2725(01)78003-8 1:CAS:528:DC%2BD3MXjtVShu7c%3D (Pubitemid 32303805)
48. A. K. Zelenin M. L. Trudell R. D. Gilardi 1998 J. Heterocycl. Chem. 35 151 10.1002/jhet.5570350128 1:CAS:528:DyaK1cXhvFWhtbk%3D
49. A. D. Becke 1988 Phys. Rev. A 38 3098 10.1103/PhysRevA.38.3098 1:CAS:528:DyaL1cXmtlOhsLo%3D
50. C. Adamo V. Barone 1999 J. Chem. Phys. 110 6158 10.1063/1.478522 1:CAS:528:DyaK1MXitVCmt7Y%3D
51. Y. Zhao N. E. Schultz D. G. Truhlar 2005 J. Chem. Phys. 123 161103 10.1063/1.2126975 (Pubitemid 41527623)
52. Y. Zhao N. E. Schultz D. G. Truhlar 2006 J. Chem. Theor. Comp. 2 364 10.1021/ct0502763
53. A. E. Reed R. B. Weinstock F. Weinhold 1985 J. Chem. Phys. 83 735 10.1063/1.449486 1:CAS:528:DyaL2MXltFSisLY%3D
54. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, T. V. Jr., 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. 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, Gaussian 03, Revision E.01, Gaussian, Inc., Wallingford CT, 2004.
55. R. S. Rowland R. Taylor 1996 J. Phys. Chem. 100 7384 10.1021/jp953141+ 1:CAS:528:DyaK28Xit1ykt7k%3D
56. F. Zhuji C. Zhiwei P. Kezhen G. Renxiao D. Zhuyue 1985 Chin. J. Struct. Chem. 4 206