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Crystal structures of racemic and enantiomeric 5-isopropyl-5-methylhydantoin
Masaki Ichitani (1)
, Soh-ichi Kitoh (2) , Keiko Tanaka (3) , Shuhei Fujinami (4) , Mitsuhiro Suda (5) , Mitsunori Honda (6) , Ko-Ki Kunimoto (7,*) (1) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(2) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(3) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(4) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(5) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(6) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(7) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(*) Corresponding Author
Received: 25 Sep 2013, Accepted: 06 Oct 2013, Published: 31 Mar 2014
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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DOI: 10.5155/eurjchem.5.1.6-10.933
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