Crystal Research and Technology
Cryst. Res. Technol. 39, 375 (2004) - Abstract -

Crystal structures and spectroscopic characterization of chiral and racemic 4-phenyl-1,3-oxazolidin-2-one

S. Kitoh, H. Senda, K.-K. Kunimoto, S. Maeda*, A. Kuwae**, and K. Hanai**

Division of Applied Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kanazawa 920-1192, Japan
*Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Fukui University, 3-9-1 Bunkyo, Fukui 910-8507, Japan
**Graduate School of Natural Sciences, Nagoya City University, Mizuho-ku, Nagoya 467-8501, Japan

Keywords 4-phenyl-1,3-oxazolidin-2-one, crystal structure, solid state 13C NMR spectra, IR spectra
PACS 08.15.Dp, 61.66.Hq
DOI 10.1002/crat.200310198

Crystal structures of (R)- and (rac)-4-phenyl-1,3-oxazolidin-2-one (4-POO) have been determined by X-ray diffraction and characterized by the solid state 13C NMR and IR spectra. Molecular geometries and intermolecular interactions in (R)- and (rac)-4-POO crystals are very similar to each other; 4-POO molecules are linked via the N-H…O intermolecular hydrogen bonds to form the chained structure. Chemical shifts of the solid state 13C NMR spectra are very similar to each other, whereas the 1H spin-lattice relaxation times (T1H) value for (R)-4-POO is five times as large as that for (rac)-4-POO, reflecting the more restricted mobility of the (R)-4-POO chain. Although both crystals contain an unique molecule in the asymmetric unit, a doublet feature is observed for the C=O stretching mode in the IR spectra of (R)- and (rac)-4-POO crystals. The frequency gap of the C=O bands are correlated with the strength of the dipole-dipole interactions between the neighboring C=O groups.



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