Skip to main content
SpringerLink
Log in

FOX-7 (1,1-Diamino-2,2-dinitroethene)

  • Chapter
  • First Online:
High Energy Density Materials

Part of the book series: Structure and Bonding ((STRUCTURE,volume 125))

Abstract

In this paper, the discovery and synthesis of the explosive 1,1-diamino-2,2-dinitroethene (FOX-7) are described, together with an account of its structural, spectroscopic, and explosive properties. The chemical reactivity of FOX-7 towards nucleophilic substitution (transamination), electrophilic substitution, and acid-base properties is explored, as is its thermal behavior (phase transformations and thermal decomposition). The molecular structure and physical properties of FOX-7 are compared with those of its three isomers (as yet unsynthesized), as derived by theoretical calculations. Finally, the physical properties of FOX-7 are compared to those of various energetic molecules that are structurally related to FOX-7.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Baum K, Bigelow SS, Nguyen NV, Archibald TA, Gilardi R, Flippen-Anderson JL (1992) J Org Chem 57:235

    Article  CAS  Google Scholar 

  2. Latypov NV, Bergman J, Langlet A, Wellmar U, Bemm U (1998) Tetrahedron 54:11525

    Article  CAS  Google Scholar 

  3. Latypov NV, Langlet A, Wellmar U (1999) WO Patent 99/03818

    Google Scholar 

  4. Latypov NV, Langlet A, Wellmar U, Goede P, Bergman J (2001) Insensitive Munitions and Energetic Materials Technology Symposium (NDIA) Bordeaux, France, p 620

    Google Scholar 

  5. Latypov NV, Johansson M, Holmgren E, Sizova EV, Sizov VV, Bellamy AJ (2007) Org Proc Res Dev 11:56

    Article  CAS  Google Scholar 

  6. Astrat'ev AA, Dashko DV, Marshin AY, Stepanov AI, Urazgil'deev NA (2001) Russian J Org Chem 37:729

    Article  Google Scholar 

  7. Lockert IJ (2001) DSTO-TR-1238

    Google Scholar 

  8. Bemm U, Östmark H (1997) Acta Cryst C54:1997

    Google Scholar 

  9. Gilardi R (1999) Cambridge Crystallographic Data Centre, CCDC 127539

    Google Scholar 

  10. Klapötke TM (2006) Ludwig-Maximilian University, Munich, Germany

    Google Scholar 

  11. Kempa PB, Herrmann M, Molina Metzger FJ, Thome V, Kjellström A, Latypov N (2004) International Annual Conference of ICT, Karlsruhe, Germany, 71:1–15

    Google Scholar 

  12. Kempa PB, Herrmann M (2005) Part Part Syst Char 22:418

    Article  CAS  Google Scholar 

  13. Bellamy AJ, Brzoska E (2003) J Ener Mater 21:43

    Article  CAS  Google Scholar 

  14. Evers J, Klapötke TM, Mayer P, Oehlinger G, Welch J (2006) Inorg Chem 45:4996

    Article  CAS  Google Scholar 

  15. Bemm U, Eriksson L (2001) Insensitive Munitions and Energetic Materials Technology Symposium (NDIA), Bordeaux, France, p 775

    Google Scholar 

  16. Östmark H, Bergmann H, Bemm U, Goede P, Holmgren E, Johannson M, Langlet A, Latypov NV, Pettersson A, Pettersson M-L, Wingborg N (2001) International Annual Conference of ICT, Karlsruhe, Germany, 26:1–21

    Google Scholar 

  17. Burnham AK, Weese RK, Wang R, Kwok QSM, Jones DEG (2005) International Annual Conference of ICT, Karlsruhe, Germany, 150:1–12

    Google Scholar 

  18. Burnham AK, Weese RK, Wang R, Kwok QSM, Jones DEG (2005) Proc North Am Therm Anal SOC CONF 33:51

    Google Scholar 

  19. Sinditskii VP, Levshenkov AI, Egorshev VY, Serushkin VV (2003) Proceedings of the 30th International Pyrotechnics Seminar, St Malo, France, p 299

    Google Scholar 

  20. Garmasheva NV, Chemagina IV, Filin VP, Kazakova MB, Loboiko BG (2004) New Trends in Research of Energetic Materials. 7th International Seminar. Pardubice, Czech Republic, p 116

    Google Scholar 

  21. Ticmanis U, Kaiser M, Pantel G, Fuhr I, Teipel U (2004) International Annual Conference of ICT, Karlsruhe, Germany, 70:1–13

    Google Scholar 

  22. Janzon B, Bergman H, Eldstäter C, Lamnevik, Östmark H (2002) 20th International Symposium on Ballistics. Orlando, FL, p 686

    Google Scholar 

  23. Matyushin YN, Afanas'ev GT, Lebedev VP, Manov MN, Pepekin VI (2003) International Annual Conference of ICT, Karlsruhe, Germany, 119:1–13

    Google Scholar 

  24. Bergman H, Östmark H, Pettersson A, Pettersson M-L, Bemm U, Hihkiö M (1999) NDIA Conference, Tampa, FL

    Google Scholar 

  25. Fraunhofer Institut for Chemische Technologie (2004) ICT Database of Thermochemical Values, Version 7.0

    Google Scholar 

  26. Akhavan J (2004) The Chemistry of Explosives, 2nd edn. Royal Soc Chem, p 78

    Google Scholar 

  27. Trzcinski WA, Cudzilo S, Chylek Z, Szymanczyk L (2006) International Annual Conference of ICT, Karlsruhe, Germany, 57:1–10

    Google Scholar 

  28. Cudzilo S, Trebinski R, Trzcinski WA, Wolanski P (1998) International Annual Conference of ICT, Karlsruhe, Germany, 150:1–8

    Google Scholar 

  29. Wild R, Teipel U (2004) International Annual Conference of ICT, Karlsruhe, Germany, 69:1–9

    Google Scholar 

  30. Cai H-Q, Shu Y-J, Yu W-F, Zeng G-Y, Cheng B-B (2004) Ener Mater 12:124

    CAS  Google Scholar 

  31. Rajappa S (1981) Tetrahedron 37:1453, (section 4.3)

    Article  CAS  Google Scholar 

  32. Marchetti L, Passalacqua V (1967) Ann Chim 57:1266

    CAS  Google Scholar 

  33. Fetell AI, Feuer H (1978) J Org Chem 43:1238

    Article  CAS  Google Scholar 

  34. Bellamy AJ, Latypov NV, Goede P (2002) J Chem Res (S)257

    Google Scholar 

  35. Bellamy AJ, Latypov NV, Goede P (2002) J Chem Research (M)0641–0661

    Google Scholar 

  36. Bellamy AJ, Goede P, Sandberg C, Latypov NV (2002) International Annual Conference of ICT, Karlsruhe, Germany, 3:1–9

    Google Scholar 

  37. Sandberg C, Latypov N, Goede P, Tryman R, Bellamy AJ (2002) New Trends in Research of Energetic Materials. 5th International Seminar. Pardubice, Czech Republic, p 292

    Google Scholar 

  38. Hervé G, Jacob G, Latypov N (2005) Tetrahedron 61:6743

    Article  CAS  Google Scholar 

  39. Baum K, Nguyen NV (1992) J Org Chem 57:3026

    Article  CAS  Google Scholar 

  40. Bellamy AJ, Latypov NV, Goede P (2003) J Chem Res (S)529

    Google Scholar 

  41. Bellamy AJ, Latypov NV, Goede P (2003) J Chem Res (M)0943–0958

    Google Scholar 

  42. Bellamy AJ, Latypov NV, Goede P (2004) New Trends in Research of Energetic Materials. 7th International Seminar. Pardubice, Czech Republic, p 75

    Google Scholar 

  43. Politzer P, Concha MC, Grice ME, Murray JS, Lane P, Habibollazadeh D (1998) J Mol Struc 452:75

    CAS  Google Scholar 

  44. Politzer P, Concha MC, Grice ME, Murray JS, Lane P, Habibollazadeh D (1998) Computational investigation of the structures and relative stabilities of amino/nitro derivatives of ethylene. J Mol Struc 452:77, reprinted with permission from Elsevier

    Google Scholar 

  45. Sorescu DC, Boatz JA, Thompson DL (2001) J Phys Chem A 105:5010

    Article  CAS  Google Scholar 

  46. Ji G-F, Xiao H-M, Dong H-S, Gong X-D, Li J-S, Wang Z-Y (2001) Acta Chim Sin 59:39

    CAS  Google Scholar 

  47. Grice ME, Habibollahzadeh D, Politzer P (1994) J Chem Phys 100:4706

    Article  CAS  Google Scholar 

  48. Zeman S (1997) Themochim Acta 302:11

    Article  CAS  Google Scholar 

  49. Zeman S (1999) J Ener Mater 17:305

    Article  CAS  Google Scholar 

  50. Zeman S (1999) Themochim Acta 333:121

    Article  CAS  Google Scholar 

  51. Zeman S, Krupka M (2003) Propell Explos Pyrotech 28:301

    Article  CAS  Google Scholar 

  52. Zeman S (2003) Propell Explos Pyrotech 28:308

    Article  CAS  Google Scholar 

  53. Licht H, Ritter H (1993) International Annual Conference of ICT 6:1–8

    Google Scholar 

  54. Hollins RA, Merwin LH, Nissan RA, Wilson WS, Gilardi R (1996) J Het Chem 33:895

    Article  CAS  Google Scholar 

  55. Pagoria PF, Mitchell AR, Schmidt RD, Simpson RL, Garcia F, Forbes J, Cutting J, Lee R, Swansiger R, Hoffman DM (1998) Insensitive Munitions & Energetic Materials Technology Symposium, San Diego, CA I-3-1–5

    Google Scholar 

  56. Pagoria P, Lee GS, Mitchell AR, Schmidt RD (2001) Insensitive Munitions & Energetic Materials Technology Symposium, Bordeaux, France 2:655

    Google Scholar 

  57. Kerth J, Kuglstatter W (2001) International Annual Conference of ICT, Karlsruhe, Germany, 166:1–11

    Google Scholar 

  58. Philbin SP, Millar RW, Coombes RG (2000) Propell Explos Pyrotech 25:302

    Article  CAS  Google Scholar 

  59. Rothstein LR, Petersen R (1979) Propell Explos 4:56

    Article  CAS  Google Scholar 

  60. Rothstein LR, Petersen R (1979) Propell Explos 4:86

    Article  Google Scholar 

  61. Rothstein LR, Petersen R (1981) Propell Explos 6:91

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Cranfield University, Defence Academy of the United Kingdom, Shrivenham, SN6 8LA, Swindon, UK

    Anthony J. Bellamy

Authors
  1. Anthony J. Bellamy
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Anthony J. Bellamy .

Editor information

T. M. Klapötke

Rights and permissions

Reprints and permissions

Copyright information

© 2007 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Bellamy, A.J. (2007). FOX-7 (1,1-Diamino-2,2-dinitroethene). In: Klapötke, T.M. (eds) High Energy Density Materials. Structure and Bonding, vol 125. Springer, Berlin, Heidelberg. https://doi.org/10.1007/430_2006_054

Download citation

Publish with us

Policies and ethics

Search

Navigation