4-(4-((5-Amino-1,3,4-thiadiazol-2-yl)methoxy)phenyl)-1-((5-amino-1,3,4-thiadiazol-2-yl)methyl)-3-benzyl-1H-1,2,4-triazol-5(4H)-one: Synthesis, Characterization and Computational Studies

Background: 1,2,4-triazole and its derivatives are known to have various biological activities such as antifungal, antiviral, antidepressant, antitumor, anti-inflammatory, antitubercular, antimigrain and anti-cancer. Computational chemistry plays an important role in determining structural and chemical properties of chemical compounds. There are many studies on computational studies of triazole derivatives. The aim of this study is to prepare new triazole derivative having potent of bio-active material and to investigate the computational properties. Methods: The molecular geometry of compound 2 was optimized by using X-ray structural parameters at the DFT calculations with a hybrid functional B3LYP (Becke’s three parameter hybrid functional using the LYP correlation functional) with the 6-31G (d,p), were performed with the Gaussian 03W software package. Results: In this work, title compound was synthesized and characterized by IR and NMR techniques. The compound was crystallized in ethanol and single crystal which suitable for X-ray analysis was obtained. The geometric optimization was studied and obtained through computational data compared with crystallographic data. Vibrational data, 1H-NMR and 13CNMR chemical shifts were calculated and compared with experimental ones. Spectral results are in agreement with each other. TD-DFT was computed and important transitions were assigned. Conclusion: Spectral results are in agreement with each other. TD-DFT was computed and important transitions were assigned. In addition, electrostatic potential map were obtained computationally. While triazole nitrogens have electrophilic character, amine groups have nucleophilic character. Moreover, natural bond orbital analysis were calculated computationally. The interactions of LP(N1) Ц#159;* (C2-N2), LP(N3) σ* (C1-O2), LP(O2) σ* (C1-N1), LP(N6) Ц#159;*(C12-N5), LP(O1) Ц#159;* (C15-C16), LP(N9) Ц#159;* (C21-N8) provide the extra stabilization energy to the molecule. The most important σ σ* interaction was obtained as σ (C3-H) σ* (C2-N1), σ (N2-N3) σ* (C2-C3), σ (N6-H) σ* (C12- S1), σ (C19-H) σ* (C20-S2), σ (N9-H) σ* (C21-S2).