European Journal of Chemistry 2014, 5(1), 6-10 | doi: https://doi.org/10.5155/eurjchem.5.1.6-10.933 | Get rights and content






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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 | Issue Date: March 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.


Keywords


Hydantoin; Enantiomer; Conglomerate; Crystal structure; Racemic compound; Imidazolidine-2,4-dione

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DOI: 10.5155/eurjchem.5.1.6-10.933

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Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Ichitani, M.; Kitoh, S.; Tanaka, K.; Fujinami, S.; Suda, M.; Honda, M.; Kunimoto, K. Eur. J. Chem. 2014, 5(1), 6-10. doi:10.5155/eurjchem.5.1.6-10.933
Ichitani, M.; Kitoh, S.; Tanaka, K.; Fujinami, S.; Suda, M.; Honda, M.; Kunimoto, K. Crystal structures of racemic and enantiomeric 5-isopropyl-5-methylhydantoin. Eur. J. Chem. 2014, 5(1), 6-10. doi:10.5155/eurjchem.5.1.6-10.933
Ichitani, M., Kitoh, S., Tanaka, K., Fujinami, S., Suda, M., Honda, M., & Kunimoto, K. (2014). Crystal structures of racemic and enantiomeric 5-isopropyl-5-methylhydantoin. European Journal of Chemistry, 5(1), 6-10. doi:10.5155/eurjchem.5.1.6-10.933
Ichitani, Masaki, Soh-ichi Kitoh, Keiko Tanaka, Shuhei Fujinami, Mitsuhiro Suda, Mitsunori Honda, & Ko-Ki Kunimoto. "Crystal structures of racemic and enantiomeric 5-isopropyl-5-methylhydantoin." European Journal of Chemistry [Online], 5.1 (2014): 6-10. Web. 6 Jun. 2020
Ichitani, Masaki, Kitoh, Soh-ichi, Tanaka, Keiko, Fujinami, Shuhei, Suda, Mitsuhiro, Honda, Mitsunori, AND Kunimoto, Ko-Ki. "Crystal structures of racemic and enantiomeric 5-isopropyl-5-methylhydantoin" European Journal of Chemistry [Online], Volume 5 Number 1 (31 March 2014)

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DOI Link: https://doi.org/10.5155/eurjchem.5.1.6-10.933

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