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

• DOI: 10.1007/s00894-009-0552-8
• Publication Date: 2009-07-11T07:35:23Z
• Authors: Namık Özdemir; Muharrem Dinçer; Alaaddin Çukurovalı
• Keywords: HF; Indoles; Magnetic Resonance Spectroscopy; Frontier molecular orbitals; Molecular Structure; Molecular Conformation; GIAO; Molecular electrostatic potential; Isoindoles; Models, Theoretical; Molecular Dynamics Simulation; Crystallography, X-Ray; DFT; X-ray structure determination; 01 natural sciences; AM1 semi-empirical method; 0104 chemical sciences; Thiazoles; Conformational analysis; IR and NMR spectroscopy; Vibrational assignment; Thermodynamics

The title compound, 2-{4-[3-(2,5-dimethylphenyl)-3-methylcyclobutyl]thiazol-2-yl}isoindoline-1,3-dione (C(24)H(22)N(2)O(2)S), 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) A, b = 6.7473(4) A, c = 15.7259(9) A and beta = 103.416(5) degrees . In addition, the molecular geometry, vibrational frequencies and gauge including atomic orbital (GIAO) (1)H and (13)C 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 degrees to +180 degrees in steps of 5 degrees . Besides, molecular electrostatic potential, frontier molecular orbitals (FMO) analysis and thermodynamic properties of the title compound were investigated by theoretical calculations.