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

Özdemir N., Dincer M., ÇUKUROVALI A.

JOURNAL OF MOLECULAR MODELING, cilt.16, sa.2, ss.291-302, 2010 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 16 Sayı: 2
  • Basım Tarihi: 2010
  • Doi Numarası: 10.1007/s00894-009-0552-8
  • Dergi Adı: JOURNAL OF MOLECULAR MODELING
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.291-302
  • Anahtar Kelimeler: AM1 semi-empirical method, Conformational analysis, DFT, Frontier molecular orbitals, GIAO, HF, IR and NMR spectroscopy, Molecular electrostatic potential, Vibrational assignment, X-ray structure determination, EFFECTIVE CORE POTENTIALS, NMR CHEMICAL-SHIFTS, ORBITAL METHODS, CONFIGURATION, CONFORMATION, SHIELDINGS, MECHANICS, ATOMS, HOLE
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

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 P2(1)/c with a = 19.7799(13) , b = 6.7473(4) , c = 15.7259(9) and beta = 103.416(5)A degrees. In addition, the molecular geometry, vibrational frequencies and gauge including atomic orbital (GIAO) H-1 and C-13 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 -180A degrees to +180A degrees in steps of 5A degrees. Besides, molecular electrostatic potential, frontier molecular orbitals (FMO) analysis and thermodynamic properties of the title compound were investigated by theoretical calculations.