European Journal of Chemistry

Crystal structures of racemic and enantiomeric 5-isopropyl-5-methylhydantoin



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Masaki Ichitani
Soh-ichi Kitoh
Keiko Tanaka
Shuhei Fujinami
Mitsuhiro Suda
Mitsunori Honda
Ko-Ki Kunimoto

Abstract

Crystal structures of racemic and enantiomeric 5-isopropyl-5-methylhydantoin (IPrMH) have been determined by single crystal X-ray diffraction. Melting temperatures and solid state infrared spectra are also measured. Racemic IPrMH has a lower melting temperature than the pure enantiomer by 25 °C. The infrared spectrum of racemic IPrMH is identical with that of the pure enantiomer. Nevertheless, the racemic IPrMH doesn’t crystallize as a conglomerate but as a racemic compound. The racemic and the enantiomeric crystals are very similar to each other in molecular geometries and intermolecular interactions. In the both cases, the molecules are connected via N−H···O hydrogen bonds to form R22(8) rings, and these rings are linked into infinite one-dimensional tapes. In the racemic crystal, a single tape is composed of single enantiomer and itself is homochiral.


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Ichitani, M.; Kitoh, S.- ichi; Tanaka, K.; Fujinami, S.; Suda, M.; Honda, M.; Kunimoto, K.-K. Crystal Structures of Racemic and Enantiomeric 5-Isopropyl-5-Methylhydantoin. Eur. J. Chem. 2014, 5, 6-10.

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