Tautomerization of diazene < => hydrazine via single proton tautomerization, spectral, XRD/HSA-interactions, optical and DFT/TD-DFT of new hydrazine ligand

A novel methyl (Z)-2-(2-(2-oxonaphthalen-1(2H)-ylidene)hydrazineyl)benzoate isomer ligand has been prepared instead of ( E )-methyl 2-((2-hydroxynaphthalen-1-yl)diazenyl)benzoate isomer in very good yield. The tautomerization of diazene to hydrazine was computed via DFT; the single proton tautomer-ization S(6) process was confirmed by XRD. Moreover, the XRD-crystal measurements supported the hy-drazine form as the preferred kinetic isomer; the structure of the desired ligand was also examined by IR, UV-vis., Carbon, Hydrogen and Nitrogen elemental analysis (CHN-EA), and NMR. Hirshfeld surface anal-ysis (HSA) computation was performed to support the lattice interactions resulting by X-ray diffraction (XRD) measurement. Furthermore, the time-dependent density functional theory (TD-DFT) and B3LYP/IR computation were used to support the UV-visible as well as FT-IR experimental results.(c) 2022 Elsevier B.V. All rights reserved.

Automated summary

A novel isomer ligand has been synthesized successfully, and the tautomerization mechanism from diazene to hydrazine has been confirmed by computational and experimental methods. The kinetic isomer of hydrazine form has been identified as the preferred form based on XRD measurements.