The 2‐(2′‐furyl)‐1H‐imidazole (1) has been prepared and characterized using infrared, Raman, and multidimensional nuclear magnetic resonance spectroscopies. Two conformations of this species obtained by rotation of 180°, approximately, around the CC inter‐ring bond are detected. Likewise, the crystal and molecular structure of 1 has been analyzed by X‐ray diffraction methods and it evidenced that both conformations are present in the lattice with equal occupancy and linked in alternate way to the NH‐‐‐N bonded polymeric chains along the crystal [101] direction. Theoretical calculations have been carried out by employing the density functional theory (DFT)/B3LYP method, in order to optimize the geometry in gas phase of both conformers and to support the assignments of the vibrational bands of 1 to their normal modes. For a complete assignment of the compound, DFT calculations were combined with Pulay's SQMFF methodology in order to fit the theoretical frequency values to the experimental one. The nuclear magnetic resonance spectrum observed for 1 is successfully compared with the calculated chemicals shifts at B3LYP/6‐311++G** level of theory for the two conformers. Furthermore, natural bond orbital (NBO) analysis and topological (AIM) calculations for an oligomer, containing three alternated units of the NH‐‐‐N bonded chain found in the crystal, reveals the characteristics of the hydrogen bonds present in the polymeric structure. Copyright © 2008 John Wiley & Sons, Ltd.

In this study 2-(2(-furyl)-4,5-1H-dihydroimidazole (1) was prepared and then characterized by infrared, Raman, and multidimensional nuclear 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 theorized for this conformer. The harmonic vibrational frequencies for the optimized geometry of the 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 Pulaý s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones.

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