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Methyl 2-methoxy-7-(4-methylbenzoyl)-4-oxo-6-p-tolyl-4H-furo[3,2-c]pyran-3-carboxylate:A combined experimental and theoretical investigation

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Abstract

The title compound, methyl 2-methoxy-7-(4-methylbenzoyl)-4-oxo-6-p-tolyl-4H-furo[3,2-c]pyran-3-carboxylate (C25H20O7), was prepared and characterized by IR and single-crystal X-ray diffraction (XRD). The compound crystallizes in the triclinic space group P −1 with a = 8.9554(9) Å, b = 10.0018(10) Å, c = 12.7454(13) Å, α = 67.678(7)°, β = 89.359(8)° and γ = 88.961(8)°. In addition to the molecular geometry from X-ray experiment, the molecular geometry and vibrational frequencies of the title compound in the ground state have been calculated using semiempirical AM1 and PM3 methods, as well as Hartree-Fock (HF) and density functional (B3LYP) levels of theory 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 and thermodynamic properties of the title compound were 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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Authors and 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, Bozok University, 66200, Yozgat, Turkey

    İrfan Koca

  3. Department of Chemistry, Faculty of Arts and Sciences, Erciyes University, 38039, Kayseri, Turkey

    İsmail Yıldırım

Authors
  1. Namık Özdemir
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  2. Muharrem Dinçer
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  3. İrfan Koca
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  4. İsmail Yıldırım
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  5. Orhan Büyükgüngör
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Correspondence to Namık Özdemir.

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Özdemir, N., Dinçer, M., Koca, İ. et al. Methyl 2-methoxy-7-(4-methylbenzoyl)-4-oxo-6-p-tolyl-4H-furo[3,2-c]pyran-3-carboxylate:A combined experimental and theoretical investigation. J Mol Model 15, 1193–1201 (2009). https://doi.org/10.1007/s00894-009-0479-0

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  • DOI: https://doi.org/10.1007/s00894-009-0479-0

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