Synthesis and amide imidic prototropic tautomerization in thiophene-2-carbohydrazide: XRD, DFT/HSA-computation, DNA-docking, TG and isoconversional kinetics via FWO and KAS models

Abstract

Thiophene-2-carbohydrazide as a novel small-molecule amide tautomer has been synthesized with an acceptable yield under microwave radiation (MW) conditions. The amide imidic thiophene-2-carbohydrazide prototropic tautomerization via single proton intramigration was computed using the DFT B3LYP/6-311G(d,p) level of theory. The endo-isomer amide structure of thiophene-2-carbohydrazide was proved by XRD and is considered to be the kinetically favored isomer. The DFT-structure parameters were compared to their corresponding XRD-experimental parameters. Several H-bond interactions were detected in the crystal lattice experimentally using the XRD-packing model then correlated to MEP and HSA calculations. The manual and calculated electronic parameters such as, frontier molecular orbital energies, excitation energy, absorption, dipole moment, DOS, GRD quantum parameters and TD-SCF/B3LYP were DFT computed. The thiophene-2-carbohydrazide isomers together with their prototropic (E)/(Z)-thiophene-2-carbohydrazonic acid tautomers were docked against 1BNA DNA. FWO and KAS isoconversional kinetic methods were applied, and the thermal behavior and estimated E_a–α relations were determined.