Theoretical and Spectroscopic Studies of (E)-3-Benzyl-4-((4- Isopropylbenzylidene)-Amino)-1-(Morpholinomethyl)-1H-1,2,4- triazol-5(4H)-one Molecule

Abstract

In this study, 1-(morpholine-4-yl-methyl)-3-benzyl-4-(4-isopropylbenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one (1) was synthesized by the reaction of compound 3-benzyl-4-(4-isopropylbenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one with morpholine and formaldehyde. The  structure of compound 1 was determined by IR, ¹H-NMR, ¹³C-NMR spectral data. Then, the synthesized compound 1 was optimized by using the B3LYP/6-31G (d,p) and HF/6-31G (d,p) basis sets. ¹H-NMR and ¹³C-NMR isotropic shift values, IR absorption frequencies, bond angles, bond lengths, the HOMO-LUMO energy, electronegativity and mulliken charges were calculated theoretically by using the program package Gaussian G09W. In addition, IR, ¹H-NMR, ¹³C-NMR theoretical spectral data were compared with certain experimental data.

Keywords

• Mannich bases
• HOMO-LUMO energy
• B3LYP 631G (d
• p)
• HF 631G (d
• Gaussian 09W

References

1. Tramontini M, Angiolini L. Mannich Bases: Chemistry and Uses. CRC Press; 1994. 289 p.
2. Yüksek H, Gürsoy O, Cakmak I, Alkan M. Synthesis and GIAO NMR calculations for some new 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives: comparison of theoretical and experimental 1H and 13C chemical shifts. Magn Reson Chem. 2005;43(May):585–7.
3. Yüksek H, Cakmak I, Sadi S, Alkan M, Baykara H. 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 1Hand 13C- Chemical Shifts. Int J Mol Sci. 2005;6(6):219–29.
4. Yüksek H, Alkan M, Bahçeci Ş, Cakmak I, Ocak Z, Baykara H, et al. Synthesis, determination of pKa values and GIAO NMR calculations of some new 3-alkyl-4-(p-methoxybenzoylamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones. J Mol Struct. 2008;873(1-3):142–8.
5. Yüksek H, Alkan M, Cakmak I, Ocak Z, Bahçeci S, Calapoglu M, et al. Preparation, GIAO NMR calculations and acidic properties of some novel 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives with their antioxidant activities. Int J Mol Sci. 2008 Jan 8;9(1):12–32.
6. Gökce H, Bahçeli S, Akyildirim O, Yüksek H, Kol ÖG. The Syntheses, Molecular Structures, Spectroscopic Properties (IR, Micro– Raman, NMR and UV–vis) and DFT Calculations of Antioxidant 3– alkyl–4–[3–methoxy–4–(4–methylbenzoxy)benzylidenamino]–4,5–dihydro– 1H–1,2,4–triazol–5–one Molecules. Lett Org Chem. 2013;10:395–441.
7. Gökce H, Akyildirim O, Bahçeli S, Yüksek H, Kol ÖG. The 1-acetyl-3-methyl-4-[3-methoxy-4-(4-methylbenzoxy)benzylidenamino]-4,5- dihydro-1H-1,2,4-triazol-5-one molecule investigated by a joint spectroscopic and quantum chemical calculations. J Mol Struct. 2014;1056-1057(1):273–84.
8. Frisch MJ, Trucks GW, Schlegel GE, Scuseria GE, Robb MA, Cheeseman JR, et al. Gaussian 09. Wallingford CT: Gaussian, Inc.; 2009.

9. Wolinski K, Hinton JF, Pulay P. Efficient Implementation of the Gauge-Independent Atomic Orbital Method for NMR Chemical Shift Calculations. J Am Chem Soc [Internet]. 1990 Nov;112(d):8251–60. DO:10.1021/ja00179a005
10. Jamroz MH. Vibrational Energy Distribution Analysis VEDA 4. Warsaw; 2010.
11. Merrick JP, Moran D, Radom L. An evaluation of harmonic vibrational frequency scale factors. J Phys Chem A. American Chemical Society; 2007;111(45):11683–700.