Abstract
In this work, the experimental synthesized bipyridines azo-bis(2-pyridine),4,4′-dimethyl-3,3′-dinitro-2,2′-azobipyridine, and N,N′-bis(3-nitro-2-pyridinyl)-methane-diamine and a set of designed bipyridines that have similar frameworks but different linkages and substituents were studied theoretically at the B3LYP/6-31G* level of density functional theory. The gas-phase heats of formation were predicted based on the isodesmic reactions, and the condensed-phase heats of formation and heats of sublimation were estimated in the framework of the Politzer approach. The crystal densities have been computed from molecular packing and results show that incorporation of –N=N–, –N=N(O)–, –CH=N–, and –NH–NH– into bipyridines is more favorable than –CH=CH– and –NH–CH2–NH– for increasing the density. The predicted detonation velocities (D) and detonation pressures (P) indicate that –NH2, –NO2, and –NF2 can enhance the detonation performance, and –NO2 and –NF2 are more favorable. Introducing –N=N–, –N=N(O)–, and –NH–NH– bridge groups into bipyridines is also favorable for improving their detonation performance. The oxidation of pyridine N always but that of –N=N– bridge does not always improve the detonation properties. E4–O, the derivative with –N=N– bridge and two –NF2 substituent groups, has the largest D (9.90 km/s) and P (47.47 GPa). An analysis of the bond dissociation energies shows that all derivatives have good thermal stability.
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The authors thank to the financial support of the National Natural Science Foundation of China and China Academy of Engineering Physics (NSAF Grant No. 11076017).
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Liu, H., Gong, XD. Comparative theoretical studies of substituted bridged bipyridines and their N-oxides. Struct Chem 24, 471–480 (2013). https://doi.org/10.1007/s11224-012-0096-x
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DOI: https://doi.org/10.1007/s11224-012-0096-x