Synthesis and GIAO NMR Calculations for Some Novel 4‑Heteroarylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives: Comparison of Theoretical and Experimental 1H- and 13C- Chemical Shifts

摘要

3-Alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1) reacted with 5-methylfuran-2-carboxyaldehyde to afford the corresponding 3-alkyl(aryl)-4-(5-methyl-2-furylmethylenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones (2). Four newly synthesized compounds have been characterized by elemental analyses, IR, 1H-NMR, 13C-NMR and UV spectral data. In addition, isotropic 1H- and 13C-nuclear magnetic shielding constants of compounds 3 were calculated by employing the direct implementation of the gauge-including-atomic-orbital (GIAO) method at the B3LYP density functional and HF levels of the theory. The geometry of each compound has been optimized using a 6-311G basis set. Nuclear shielding constants were also calculated by using 6-311G basis set.  Theoretical values are compared to the experimental data.