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

ÖZDEMİR N., DİNÇER M., KOCA İ., YILDIRIM İ., BÜYÜKGÜNGÖR O.

JOURNAL OF MOLECULAR MODELING, cilt.15, sa.10, ss.1193-1201, 2009 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 15 Sayı: 10
  • Basım Tarihi: 2009
  • Doi Numarası: 10.1007/s00894-009-0479-0
  • Dergi Adı: JOURNAL OF MOLECULAR MODELING
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1193-1201
  • Anahtar Kelimeler: Ab-initio calculation, AM1 and PM3 semiempirical methods, B3LYP, Conformational analysis, Hartree-Fock, Vibrational assignment, X-ray structure determination, APOPTOSIS INDUCERS, DERIVATIVES, DISCOVERY, EPOXIDES, SERIES
  • Yozgat Bozok Üniversitesi Adresli: Evet

Özet

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) , b = 10.0018(10) , c = 12.7454(13) , alpha = 67.678(7)A degrees, beta = 89.359(8)A degrees and gamma = 88.961(8)A degrees. 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 -180A degrees to +180A degrees in steps of 10A degrees. Besides, frontier molecular orbitals (FMO) analysis and thermodynamic properties of the title compound were performed by the B3LYP/6-31G(d) method.