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An experimental and theoretical approach to the molecular structure of 2-{4-[3-(2,5-dimethylphenyl)-3-methylcyclobutyl]thiazol-2-yl}isoindoline-1,3-dione

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Abstract

The title compound, 2-{4-[3-(2,5-dimethylphenyl)-3-methylcyclobutyl]thiazol-2-yl}isoindoline-1,3-dione (C24H22N2O2S), was synthesized and characterized by IR-NMR spectroscopy and single-crystal X-ray diffraction. The compound crystallizes in the monoclinic space group P21/c with a = 19.7799(13) Å, b = 6.7473(4) Å, c = 15.7259(9) Å and β = 103.416(5)°. In addition, the molecular geometry, vibrational frequencies and gauge including atomic orbital (GIAO) 1H and 13C chemical shift values of the title compound in the ground state have been calculated by using the Hartree-Fock (HF) and density functional method (DFT/B3LYP) with 6–31G(d), 6–31 + G(d,p) and LANL2DZ basis sets, and compared with the experimental data. 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 5°. Besides, molecular electrostatic potential, frontier molecular orbitals (FMO) analysis and thermodynamic properties of the title compound were investigated by theoretical calculations.

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Acknowledgments

This study was supported financially by the Research Centre of Ondokuz Mayıs University (Project No: F-461).

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Authors and Affiliations

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

    Namık Özdemir & Muharrem Dinçer

  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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Correspondence to Namık Özdemir.

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Özdemir, N., Dinçer, M. & Çukurovalı, A. An experimental and theoretical approach to the molecular structure of 2-{4-[3-(2,5-dimethylphenyl)-3-methylcyclobutyl]thiazol-2-yl}isoindoline-1,3-dione. J Mol Model 16, 291–302 (2010). https://doi.org/10.1007/s00894-009-0552-8

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  • DOI: https://doi.org/10.1007/s00894-009-0552-8

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