Nitro cubanes

Nitrocubanes are probably the most powerful explosives with a predicted detonation velocity of >10,000 ms-1. Cubanes were first synthesised at the University of Chicago, USA by Eaton and Cole in 1964. The US Army Armament Research Development Centre (ARDEC) then funded development into the formation of octanitrocubane [(ONC) (C8N8016)] and heptanitrocubane [(HpNC) (C8N7014)]. ONC and HpNC were successfully synthesised in 1997 and 2000 respectively by Eaton and co-workers. The basic structure of ONC is a cubane molecule where all the hydrogens have been replaced by nitro groups (1.6). HpNC is denser than ONC and predicted to be a more powerful, shock-insensitive explosive. 

The acidity of 1,3,5,7-tetranitrocubane, which features nitro groups on alternate comers of cubane, has been measured (p/C, 21) and reactions of the corresponding o-nitro anion have been explored.183... 

Fig. 5. Crystal density vs number of nitro groups for various cubanes Table 8...

G. Zhou, J. L. Zhang, N. B. Wong, and A. Tian, Theoretical study of the blue-shifting intramolecular hydrogen bonds of nitro derivatives of cubane, J. Mol. Struct. (Theochem) 639, 43-51 (2003). 

J, S. Murray, J. M. Seminario, and P. Politzer, Struct. Chem., 2, 153 (1990). Effects of the Simultaneous Presence of Nitro and Amine Substituents in Cubane and Some Azacubanes. 

---