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Theoretical studies on 2‐(5‐amino‐3‐nitro‐1,2,4‐triazolyl)‐3,5‐dinitropyridine (PRAN) and its derivatives
Author(s) -
Liu Hui,
Wang Fang,
Wang GuiXiang,
Gong XueDong
Publication year - 2013
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3013
Subject(s) - isodesmic reaction , chemistry , detonation , bond dissociation energy , standard enthalpy of formation , basis set , nitro , density functional theory , detonation velocity , computational chemistry , derivative (finance) , dissociation (chemistry) , thermodynamics , organic chemistry , explosive material , alkyl , physics , financial economics , economics
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.