Structural and vibrational study of 2-(2'-furyl)-4,5-1H dihydroimidazole

J. ZINCZUK; A. E. LEDESMA; S. A. BRANDÁN; O. E. PIRO; J. J. LÓPEZ GONZÁLEZ; A. BEN ALTABEF

J. Phys. Org. Chem.

John Wiley & Sons

Año: 2009 vol. 22 p. 1166 - 1177

1099-1395

In this study 2-(2(-furyl)-4,5-1H-dihydroimidazole (1) was prepared and then it was characterized by infrared, Raman, and multidimensional nuclearQ3 magnetic resonance (NMR) spectroscopies. The crystal and molecular structures of 1 were determined by X-ray diffraction methods. The density functional theory (DFT) and second-order Møller–Plesset theory (MP2) with Pople’s basis set show that there are two conformers for the title molecule that have been theoretically determined in the gas phase, and that only one of them, conformer I, is present in the solid phase. NMR spectra observed for 1 were successfully compared with the calculated chemical shifts at the B3LYP/6-311RRG** level of the theory for this conformer. The harmonic vibrational frequencies for the optimized geometry of this latter conformer were calculated at the B3LYP/6-311RRG** level in the approximation of the isolated molecule. For a complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. of the theory for this conformer. The harmonic vibrational frequencies for the optimized geometry of this latter conformer were calculated at the B3LYP/6-311RRG** level in the approximation of the isolated molecule. For a complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. were determined by X-ray diffraction methods. The density functional theory (DFT) and second-order Møller–Plesset theory (MP2) with Pople’s basis set show that there are two conformers for the title molecule that have been theoretically determined in the gas phase, and that only one of them, conformer I, is present in the solid phase. NMR spectra observed for 1 were successfully compared with the calculated chemical shifts at the B3LYP/6-311RRG** level of the theory for this conformer. The harmonic vibrational frequencies for the optimized geometry of this latter conformer were calculated at the B3LYP/6-311RRG** level in the approximation of the isolated molecule. For a complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. of the theory for this conformer. The harmonic vibrational frequencies for the optimized geometry of this latter conformer were calculated at the B3LYP/6-311RRG** level in the approximation of the isolated molecule. For a complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. and multidimensional nuclearQ3 magnetic resonance (NMR) spectroscopies. The crystal and molecular structures of 1 were determined by X-ray diffraction methods. The density functional theory (DFT) and second-order Møller–Plesset theory (MP2) with Pople’s basis set show that there are two conformers for the title molecule that have been theoretically determined in the gas phase, and that only one of them, conformer I, is present in the solid phase. NMR spectra observed for 1 were successfully compared with the calculated chemical shifts at the B3LYP/6-311RRG** level of the theory for this conformer. The harmonic vibrational frequencies for the optimized geometry of this latter conformer were calculated at the B3LYP/6-311RRG** level in the approximation of the isolated molecule. For a complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. of the theory for this conformer. The harmonic vibrational frequencies for the optimized geometry of this latter conformer were calculated at the B3LYP/6-311RRG** level in the approximation of the isolated molecule. For a complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. were determined by X-ray diffraction methods. The density functional theory (DFT) and second-order Møller–Plesset theory (MP2) with Pople’s basis set show that there are two conformers for the title molecule that have been theoretically determined in the gas phase, and that only one of them, conformer I, is present in the solid phase. NMR spectra observed for 1 were successfully compared with the calculated chemical shifts at the B3LYP/6-311RRG** level of the theory for this conformer. The harmonic vibrational frequencies for the optimized geometry of this latter conformer were calculated at the B3LYP/6-311RRG** level in the approximation of the isolated molecule. For a complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. of the theory for this conformer. The harmonic vibrational frequencies for the optimized geometry of this latter conformer were calculated at the B3LYP/6-311RRG** level in the approximation of the isolated molecule. For a complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. (-furyl)-4,5-1H-dihydroimidazole (1) was prepared and then it was characterized by infrared, Raman, and multidimensional nuclearQ3 magnetic resonance (NMR) spectroscopies. The crystal and molecular structures of 1 were determined by X-ray diffraction methods. The density functional theory (DFT) and second-order Møller–Plesset theory (MP2) with Pople’s basis set show that there are two conformers for the title molecule that have been theoretically determined in the gas phase, and that only one of them, conformer I, is present in the solid phase. NMR spectra observed for 1 were successfully compared with the calculated chemical shifts at the B3LYP/6-311RRG** level of the theory for this conformer. The harmonic vibrational frequencies for the optimized geometry of this latter conformer were calculated at the B3LYP/6-311RRG** level in the approximation of the isolated molecule. For a complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. of the theory for this conformer. The harmonic vibrational frequencies for the optimized geometry of this latter conformer were calculated at the B3LYP/6-311RRG** level in the approximation of the isolated molecule. For a complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. were determined by X-ray diffraction methods. The density functional theory (DFT) and second-order Møller–Plesset theory (MP2) with Pople’s basis set show that there are two conformers for the title molecule that have been theoretically determined in the gas phase, and that only one of them, conformer I, is present in the solid phase. NMR spectra observed for 1 were successfully compared with the calculated chemical shifts at the B3LYP/6-311RRG** level of the theory for this conformer. The harmonic vibrational frequencies for the optimized geometry of this latter conformer were calculated at the B3LYP/6-311RRG** level in the approximation of the isolated molecule. For a complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. of the theory for this conformer. The harmonic vibrational frequencies for the optimized geometry of this latter conformer were calculated at the B3LYP/6-311RRG** level in the approximation of the isolated molecule. For a complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. nuclearQ3 magnetic resonance (NMR) spectroscopies. The crystal and molecular structures of 1 were determined by X-ray diffraction methods. The density functional theory (DFT) and second-order Møller–Plesset theory (MP2) with Pople’s basis set show that there are two conformers for the title molecule that have been theoretically determined in the gas phase, and that only one of them, conformer I, is present in the solid phase. NMR spectra observed for 1 were successfully compared with the calculated chemical shifts at the B3LYP/6-311RRG** level of the theory for this conformer. The harmonic vibrational frequencies for the optimized geometry of this latter conformer were calculated at the B3LYP/6-311RRG** level in the approximation of the isolated molecule. For a complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. of the theory for this conformer. The harmonic vibrational frequencies for the optimized geometry of this latter conformer were calculated at the B3LYP/6-311RRG** level in the approximation of the isolated molecule. For a complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. RRG** level of the theory for this conformer. The harmonic vibrational frequencies for the optimized geometry of this latter conformer were calculated at the B3LYP/6-311RRG** level in the approximation of the isolated molecule. For a complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones. RRG** level in the approximation of the isolated molecule. For a complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulay´ s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones.