Chemical Papers

, Volume 65, Issue 3, pp 380–388 | Cite as

Theoretical studies on polynitrobicyclo[1.1.1]pentanes in search of novel high energy density materials

  • Vikas D. GhuleEmail author
  • Radhakrishnan Sarangapani
  • Pandurang M. Jadhav
  • Surya P. Tewari


Bicyclo[1.1.1]pentane is a highly strained hydrocarbon system due to close proximity of nonbonded bridge head carbons. Based on fully optimized molecular geometries at the density functional theory using the B3LYP/6-31G* level, densities, detonation velocities, and pressures for a series of polynitrobicyclo[1.1.1]pentanes, as well as their thermal stabilities were investigated in search for high energy density materials (HEDMs). The designed compounds with more than two nitro groups are characterized by high heat of formation and magnitude correlative with the number and space distance of nitro groups. Density was calculated using the crystal packing calculations and an increase in the number of nitro groups increases the density. The increase in density shows a linear increase in the detonation characteristics. Bond dissociation energy was analyzed to determine thermal stability. Calculations of the bond length and bond dissociation energies of the C-NO2 bond indicate that this may be the possible trigger bond in the pyrolysis mechanism. 1,2,3-Trinitrobicyclo[1.1.1]pentane (S3), 1,2,3,4-tetranitrobicyclo[1.1.1]pentane (S4), and 1,2,3,4,5-pentanitrobicyclo[1.1.1]pentane (S5) have better energetic characteristics with better stability and insensitivity, and as such may be explored in defense applications as promising candidates of the HEDMs series.


bicyclo[1.1.1]pentane HEDM density functional theory heat of formation bond dissociation energy density 


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Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2011

Authors and Affiliations

  • Vikas D. Ghule
    • 1
    Email author
  • Radhakrishnan Sarangapani
    • 2
  • Pandurang M. Jadhav
    • 2
  • Surya P. Tewari
    • 1
  1. 1.Advanced Centre of Research in High Energy Materials (ACRHEM)University of HyderabadHyderabadIndia
  2. 2.High Energy Materials Research Laboratory (HEMRL)PuneIndia

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