Publication Date:
2012-08-19
Description:
In this work, a set of derivatives of 2-(5-amino-3-nitro-1,2,4-triazolyl)-3,5-dinitropyridine (PRAN) with different energetic substituents (−N 3 , –NO 2 , –NH 2 , –NF 2 ) have been studied at the Becke, three-parameter, Lee–Yang–Parr/aug-cc-pvdz, Becke, three-parameter, Lee–Yang–Parr/6-31G(d), Becke, three-parameter, Perdew 86/6-31G(d), and Becke three-parameter, Perdew–Wang 91/6-31G(d,p) levels of density functional theory. The gas-phase heats of formation were predicted with isodesmic reactions and the condensed-phase HOFs were estimated with the Politzer approach. The effects of different functionals and basis sets were analyzed. –N 3 and –NO 2 greatly increase while –NH 2 and –NF 2 slightly decrease heats of formation. An analysis of the bond dissociation energies and impact sensitivity shows that all compounds have good stability. The crystal densities (1.82–2.00 g/cm 3 ) computed from molecular packing calculations are big for all compounds and that of the –NF 2 derivative is the largest. All derivatives have higher detonation velocity and detonation pressure than PRAN. Compounds 3 and 4 (R = NO 2 and NF 2 ) have better performance than hexahydro-1,3,5-trinitro-1,3,5-trizine and the performance of 4 is quite close to that of 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane, they are promising candidates of high energy compounds and worth further investigations. Copyright © 2012 John Wiley & Sons, Ltd. The heats of formation, detonation performances, and sensitivity of PRAN and its derivatives were studied and found they are promising candidates of high energy compounds.
Print ISSN:
0894-3230
Electronic ISSN:
1099-1395
Topics:
Chemistry and Pharmacology
,
Physics
Permalink