Skip to main content
Log in

Synthesis and structure of 4-[(4-Nitro-1,2,5-oxadiazol-3-yl)-NNO-azoxyl]-1, 2,5-oxadiazol-3-amine

  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

The synthesis of the energetic compound 4-[(4-nitro-1,2,5-oxadiazol-3-yl)-NNO-azoxyl]-1,2,5-oxadiazol-3-amine (3) was achieved in two steps from diaminofurazan (1). Compound 3 was characterized by X-ray diffraction. From the X-ray structure a bifurcated intramolecular H bond between O(2)-H(2)-N(4) was observed. In addition, intramolecular H bonding was observed between H(1) and N(7)′ of an adjacent molecule. One molecule of ethanol and one-half molecule of water per molecule of3 was observed in the crystal lattice. However, no H bonding was observed between the solvent molecules and3 in the crystal lattice. Despite the presence of solvent in the crystal lattice,3 was found to have a high crystal density (d=1.856 g/cm3).

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Stoner, C. E., Jr.; Brill, T. B.Combustion Flame 1991,83, 302.

    Google Scholar 

  2. Brill, T. B.Prog. Energy Combust. Sci. 1992,18, 91–116.

    Google Scholar 

  3. Williams, G. K.; Palopoli, S. F.; Brill, T. B.Combustion Flame 1994,98, 197–204.

    Google Scholar 

  4. Gunasekaran, A.; Trudell, M. L.; Boyer, J. H.Heteroatom Chem. 1994,5/6, 441.

    Google Scholar 

  5. Data obtained from Stephen A. Aubert, Eglin Air Force Base, Florida.

  6. Meyer, R.Explosives; VCH: Weinheim, 1987, p. 266.

    Google Scholar 

  7. Novikova, T. S.; Melnikova, T. M.; Kharitonova, O. V.; Kulagina, V. O.; Aleksandrova, N. S.; Sheremetev, A. V.; Pivina, T. S.: Khmelnitskii, L. I.; Novikov, S. S.Mendeleev Commun. 1994, 138.

  8. Cady, H. H.; Carson, A. C.Acta Crystallogr. 1967,23, 601.

    Google Scholar 

  9. Urbanski, T.; Vasudeva, S. K.J. Sci. Ind. Res. 1978,37, 250.

    Google Scholar 

  10. The densityd(g/cm3), detonation velocityD (mm/μsec), and detonation pressurePCJ (kbar) were computed with a program (Dickerson Method) obtained from the Naval Weapons Center, China Lake, CA.

  11. Gunasekaran, A.; Jayachandran, T.; Boyer, J. H.; Trudell, M. L.J. Heterocycl. Chem. 1995,32, 1405.

    Google Scholar 

  12. Solodyuk, G. D.; Boldyrev, M. D.; Gidaspov, B. V.; Nikolaev, V. D.Zh. Org. Khim. 1981,17, 861 [English translation, p. 756].

    Google Scholar 

  13. The authors have deposited the crystallographic data for3 at the Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, U.K.

  14. Frenz, B. A. InComputing in Crystallography; Schenk, M.; Oltholf-Hazekamp, R.; van Koningsveld, M.; Bassi, G. C., eds.; Delft University Press: Delft, The Netherlands, 1982.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mark L. Trudell.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zelenin, A.K., Stevens, E.D. & Trudell, M.L. Synthesis and structure of 4-[(4-Nitro-1,2,5-oxadiazol-3-yl)-NNO-azoxyl]-1, 2,5-oxadiazol-3-amine. Struct Chem 8, 373–377 (1997). https://doi.org/10.1007/BF02281251

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02281251

Key words

Navigation