A Computational View of PATO and its Tautomers

Date

2012-07-01

Author

Türker, Burhan Lemi
Bayar, Caglar Celik

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1, 2, 4-Triazole and 3-amino-1, 2, 4-triazole are useful starting materials for the synthesis of many 1, 2, 4-triazole-based explosives. Electronic properties and KamletJacobs detonation performances of PATO (3-picrylamino-1, 2, 4-triazole) (a relatively inexpensive, insensitive, and thermally stable explosive) and its 1, 3- and 1, 5- tautomers are investigated computationally using PM3, HF/6-31G(d, p), and B3LYP/6-31G(d, p) methods. The relationships between the thermodynamic and kinetic stabilities and the aromaticities are examined for all structures and their relative sensitivities are compared in terms of bond dissociation energies. The use of both PM3 and isodesmic methods in the calculation of heat of formation of PATO is discussed.

Subject Keywords

Aromaticity, Density functional calculations, Detonation performance, Tautomerism, 3-Picrylamino-1, 4-triazole (PATO)

URI

https://hdl.handle.net/11511/51811

Collections

Department of Chemistry, Article