Harris, Nathan J.’s team published research in Journal of the American Chemical Society in 118 | CAS: 63598-71-0

Journal of the American Chemical Society published new progress about 63598-71-0. 63598-71-0 belongs to triazoles, auxiliary class Triazole, name is 4H-1,2,4-Triazole, and the molecular formula is C2H3N3, Quality Control of 63598-71-0.

Harris, Nathan J. published the artcileTautomerism, Ionization, and Bond Dissociations of 5-Nitro-2,4-dihydro-3H-1,2,4-triazolone, Quality Control of 63598-71-0, the publication is Journal of the American Chemical Society (1996), 118(34), 8048-8055, database is CAplus.

Tautomerization, ionization, and bond dissociations of the insensitive high-energy explosive 5-nitro-2,4-dihydro-3H-1,2,4-triazolone (I) were studied by MO SCF and MP2 theories and with the Becke3LYP hybrid d. functional using the 6-31+G* and 6-311+G** basis sets. Energies computed with these methods were compared against accurate G2 energies for the tautomerization, ionization, and bond dissociations of nitromethane. The Becke3LYP and MP2/6-31+G* structures of the anion (II) compare well with the reported x-ray structure of the I diaminoguanidinium salt. The IR frequencies calculated with Becke3LYP compare well with those observed for crystalline I. Two enol tautomers with 1H-1,2,4-triazole skeletons are only 4 kcal/mol at MP2/6-311+G** (and 9 kcal/mol at Becke3LYP/6-311+G**) less stable than I, while the two aci-nitro tautomers are ca. 30 kcal/mol less stable than I. Comparisons of bond lengths, calculated proton chem. shifts, and magnetic susceptibility anisotropies show the enol tautomers are more aromatic than I, which accounts for their enhanced stabilities. II is also more aromatic than I, which partly explains its small proton affinity of 321 kcal/mol calculated at Becke3LYP/6-311+G**+ZPE. The estimated N-H and C-NO2 bond dissociation energies for I are, resp., 93 and 70 kcal/mol, and that for the N-OH bond of the aci-nitro tautomer III is 38 kcal/mol. Some possible processes in the initial stages of I decomposition are bimol. hydrogen atom transfers (in the condensed phase), C-NO2 bond homolysis (at high temperatures or under conditions of shock or impact), and homolysis of the N-OH bond in the aci-nitro tautomers.

Journal of the American Chemical Society published new progress about 63598-71-0. 63598-71-0 belongs to triazoles, auxiliary class Triazole, name is 4H-1,2,4-Triazole, and the molecular formula is C2H3N3, Quality Control of 63598-71-0.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics