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Experimental and theoretical investigation of the molecular and electronic structure of 5-(4-aminophenyl)-4-(3-methyl-3-phenylcyclobutyl)thiazol-2-amine

Journal of Molecular Modeling volume 15, Article number: 1435 (2009) Cite this article

Abstract

The title molecule, 5-(4-aminophenyl)-4-(3-methyl-3-phenylcyclobutyl)thiazol-2-amine (C20H21N3S), was prepared and characterized by 1H-NMR, 13C-NMR, IR and single-crystal X-ray diffraction. The compound crystallizes in the monoclinic space group P21/c with a = 9.4350(5) Å, b = 11.2796(6) Å, c = 18.4170(8) Å and β = 113.378(3)°. In addition to the molecular geometry from X-ray experiment, the molecular geometry, vibrational frequencies, gauge including atomic orbital (GIAO) 1H- and 13C-NMR chemical shift values and atomic charges distribution of the title compound in the ground state have been calculated using the Hartree–Fock (HF) and density functional method (DFT) (B3LYP) with 6-31G(d) basis set. To determine conformational flexibility, molecular energy profile of the title compound was obtained by semi-empirical (AM1) calculations with respect to two selected degrees of torsional freedom, which were varied from −180° to +180° in steps of 10°. Besides, frontier molecular orbitals (FMO) analysis was performed by the B3LYP/6-31G(d) method.

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Acknowledgments

This study was supported financially by the Research Centre of Ondokuz Mayıs University (Project No: F-425).

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Affiliations

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

    Namık Özdemir, Muharrem Dinçer & Orhan Büyükgüngör

  2. Department of Chemistry, Faculty of Arts and Sciences, Fırat University, 23119, Elazığ, Turkey

    Alaaddin Çukurovalı

Authors
  1. Namık Özdemir
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  2. Muharrem Dinçer
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  3. Alaaddin Çukurovalı
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  4. Orhan Büyükgüngör
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Correspondence to Namık Özdemir.

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Özdemir, N., Dinçer, M., Çukurovalı, A. et al. Experimental and theoretical investigation of the molecular and electronic structure of 5-(4-aminophenyl)-4-(3-methyl-3-phenylcyclobutyl)thiazol-2-amine. J Mol Model 15, 1435 (2009). https://doi.org/10.1007/s00894-009-0509-y

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  • DOI: https://doi.org/10.1007/s00894-009-0509-y

Keywords

  • Ab-initio calculation
  • AM1 semi-empirical method
  • B3LYP
  • Conformational analysis
  • Hartree–Fock
  • NMR spectroscopy
  • Vibrational assignment
  • X-ray structure determination