A Computational View of PATO and its Tautomers

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 Kamlet–Jacobs 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.