Bean, Gerritt P. published the artcileApplication of Natural Bond Orbital Analysis and Natural Resonance Theory to Delocalization and Aromaticity in Five-Membered Heteroaromatic Compounds, Product Details of C2H3N3, the publication is Journal of Organic Chemistry (1998), 63(8), 2497-2506, database is CAplus and MEDLINE.
The various measures of delocalization in all of the five-membered nitrogen and oxygen heteroaromatic compounds (azoles and oxoles) were obtained from MO calculations at the HF/6-31G* level and the application of natural bond orbital anal. and natural resonance theory. The hydrogen transfer and aromatic energies of these compounds were also calculated These were compared to the relative ranking of aromaticity reported by Katritzky from a principal component anal. of other measures of aromaticity. It was concluded that the extent of the transfer of electron d. from the pz orbital of the heteroatom to the rest of the π system is the best measure of delocalization and “aromaticity” of these compounds This indicated that all of the oxoles are less delocalized than any of the azoles because the electronegativity of the oxygen atom prevents the interaction of its lone pair of electrons with the π system. For this reason the range of delocalization in the oxoles is also much narrower. The degree of delocalization in the π system is the result of the geometry imposed by the σ structure, which in turn is defined by the identity and arrangement of the atoms of the ring.
Journal of Organic Chemistry 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, Product Details of C2H3N3.
Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics