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Experimental and DFT computational studies on 5-benzyl-4-(3,4-dimethoxyphenethyl)-2H-1,2,4-triazol-3(4H)-one

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Abstract

The triazole compound, 5-benzyl-4-(3,4-dimethoxyphenethyl)-2H-1,2,4-triazol-3(4H)-one, has been synthesized and characterized by 1H-NMR, 13C-NMR, IR, and X-ray single-crystal determination. The compound crystallizes in the monoclinic space group P21 with a = 11.8844(3) Å, b = 17.5087(4) Å, c = 17.3648(6) Å, β = 99.990(2)˚ and Z = 8. In addition to the molecular geometry from X-ray experiment, the molecular geometry, vibrational frequencies and gauge including atomic orbital (GIAO) 1H- and 13C-NMR chemical shift values of the title compound in the ground state have been calculated using the density functional method (B3LYP) with 6-31G(d,p) basis set. The calculated results show that the optimized geometries can well reproduce the crystal structure and the theoretical vibrational frequencies and chemical shift values show good agreement with experimental ones. Besides, molecular electrostatic potential (MEP), natural bond orbital (NBO), and frontier molecular orbitals (FMO) analysis of the title compound were performed by the B3LYP/6-31G(d,p) method.

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Acknowledgments

This study was supported financially by the Research Centre of Ondokuz Mayıs University (Project No: F-476).

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Authors and Affiliations

  1. Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139, Kurupelit, Samsun, Turkey

    Hasan Tanak, Metin Yavuz & Orhan Büyükgüngör

  2. Samsun Vocational School, Ondokuz Mayıs University, 55139, Kurupelit, Samsun, Turkey

    Yavuz Köysal

  3. Department of Chemistry, Faculty of Arts and Sciences, Karadeniz Technical University, 61080, Trabzon, Turkey

    Kemal Sancak

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  1. Hasan Tanak
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Correspondence to Hasan Tanak.

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Tanak, H., Köysal, Y., Yavuz, M. et al. Experimental and DFT computational studies on 5-benzyl-4-(3,4-dimethoxyphenethyl)-2H-1,2,4-triazol-3(4H)-one. J Mol Model 16, 447–457 (2010). https://doi.org/10.1007/s00894-009-0559-1

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