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

Issue cover





  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.5.1.6-10.933

Links for Article


| | | | | | |

| | | | | | |

| | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 1010 times | icon graph PDF Article downloaded 426 times


Citations

/


[1]. Yong-Ming Yan, Xiao-Hui Meng, Hong-Fu Bai, Yong-Xian Cheng
Nonpeptide small molecules with a ten-membered macrolactam or a morpholine motif from the insect American cockroach and their antiangiogenic activity
Organic Chemistry Frontiers  , , 2021
DOI: 10.1039/D0QO01653E
/


References


[1]. Mutschler, E.; Derendorf, H. Drug Actions, Basic Principles and Therapeutic Aspects, Medpharm Scientific Publishers, Stuttgart, 1995.

[2]. Knabe, J.; Baldauf, J.; Ahlhem, A. Pharmazie 1997, 52, 912-919.

[3]. Dylag, T.; Zygmunt, M.; Maciag, D.; Handzlik, J.; Bednarski, M.; Filipek, B.; Kiec-Kononowicz, K. Eur. J. Med. Chem. 2004, 39, 1013-1027.
http://dx.doi.org/10.1016/j.ejmech.2004.05.008

[4]. Opacic, N.; Barbaric, M.; Zorc, B.; Cetina, M.; Nagl, A.; Frkovic, D.; Kralj, M.; Pavelic, K.; Balzarini, J.; Andrei, G.; Snoeck, R.; De Clercq, E.; Raic-Malic, S.; Mintas, M. J. Med. Chem. 2005, 48, 475-482.
http://dx.doi.org/10.1021/jm040869i

[5]. Lattmann, E.; Ayuko, W. O.; Kinchinaton, D.; Langley, C. A.; Singh, H.; Karimi, L.; Tisdale, M. J. J. Phar. Pharmacol. 2003, 55, 1259-1265.
http://dx.doi.org/10.1211/0022357021756

[6]. Carmi, C.; Cavazzoni, A.; Zuliani, V.; Lodola, A.; Bordi, F.; Plazzi, P. V.; Alfieri, R. R.; Petronini, P. G.; Mor, M. Bioorg. Med. Chem. Lett. 2006, 16, 4021-4025.
http://dx.doi.org/10.1016/j.bmcl.2006.05.010

[7]. Singh, G.; Driever, P. H.; Sander, J. W. Brain 2005, 128, 7-17.
http://dx.doi.org/10.1093/brain/awh363

[8]. Kaindl, A. M.; Asimiadou, S.; Manthey, D.; Hagen, M. V.; Turski, L.; Ikonomidou, C. Cell. Mol. Life Sci. 2006, 63, 399-413.
http://dx.doi.org/10.1007/s00018-005-5348-0

[9]. Tompkins, J. E. J. Med. Chem. 1986, 29, 855-859.
http://dx.doi.org/10.1021/jm00155a042

[10]. Takahashi, A.; Matsuoka, H.; Yamada, K.; Uda, Y. Food Chem. Toxicol. 2005, 43, 521-528.
http://dx.doi.org/10.1016/j.fct.2004.12.005

[11]. Al-Madi, S. H.; Al-Obaid, A. M.; El-Subbagh, H. I. Anti-Cancer Drugs 2001, 12, 835-839.
http://dx.doi.org/10.1097/00001813-200111000-00007

[12]. Shiozaki, M. Carbohyd. Res. 2002, 337, 2077-2088.
http://dx.doi.org/10.1016/S0008-6215(02)00217-3

[13]. Marton, J.; Enisz, J.; Hosztafi, S.; Timar, T. J. Agric. Food. Chem. 1993, 41, 148-152.
http://dx.doi.org/10.1021/jf00025a031

[14]. Jha, S.; Silversides, J. D.; Boyle, R. W.; Archibald, S. J. Cryst. Eng. Comm. 2010, 12, 1730-1739.
http://dx.doi.org/10.1039/b924683e

[15]. Cruz-Cabeza, A. J.; Schwalbe, C. H. New J. Chem. 2012, 36, 1347-1354.
http://dx.doi.org/10.1039/c2nj21060f

[16]. Ogawa, T.; Kitoh, S.; Ichitani, M.; Kuwae, A.; Hanai, K.; Kunimoto, K. Anal. Sci. X-ray Struct. Anal. Online 2007, 23, x199-x200.
http://dx.doi.org/10.2116/analscix.23.x199

[17]. Ogawa, T.; Kitoh, S.; Okagawa, M.; Ichitani, M.; Kuwae, A.; Hanai, K.; Kunimoto, K. Anal. Sci. X-ray Struct. Anal. Online 2007, 23, x201-x202.
http://dx.doi.org/10.2116/analscix.23.x201

[18]. Kunimoto, K.; Ichitani, M.; Ogawa, T.; Kitoh, S.; Kuwae, A.; Hanai, K. Spectrosc. Lett. 2009, 42, 73-80.
http://dx.doi.org/10.1080/00387010802428575

[19]. Ogawa, T.; Okumura, H.; Honda, M.; Suda, M.; Fujinami, S.; Kuwae, A.; Hanai, K.; Kunimoto, K. Anal. Sci. X-ray Struct. Anal. Online 2009, 25, 91-92.

[20]. Taniguchi, K.; Okumura, H.; Honda, M.; Suda, M.; Fujinami, S.; Kuwae, A.; Hanai, K.; Maeda, S.; Kunimoto, K. Anal. Sci. X-ray Struct. Anal. Online 2009, 25, 93-94.

[21]. Ichitani, M.; Kitoh, S.; Fujinami, S.; Suda, M.; Honda, M.; Kunimoto, K. Acta Cryst. E 2013, 69, o953-o953.
http://dx.doi.org/10.1107/S1600536813013639

[22]. Ichitani, M.; Kitoh, S.; Tanaka, K.; Fujinami, S.; Suda, M.; Honda, M.; Kuwae, A.; Hanai, K.; Kunimoto, K. Eur. J. Chem. 2013, 4, 350-352.
http://dx.doi.org/10.5155/eurjchem.4.4.350-352.872

[23]. Rigaku CrystalClear, Rigaku Corporation, Tokyo, Japan, 2006.

[24]. Rigaku REQAB, Rigaku Corporation, Tokyo, Japan, 1998.

[25]. Burla, M. C.; Caliandro, R.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; De Caro, L.; Giacovazzo, C.; Polidori, G.; Siliqi, D.; Spagna, R. J. Appl. Cryst. 2007, 40, 609-613.
http://dx.doi.org/10.1107/S0021889807010941

[26]. Sheldrick, G. M. Acta Cryst. A 2008, 64, 112-122.
http://dx.doi.org/10.1107/S0108767307043930

[27]. Rigaku CrystalStructure, Rigaku Corporation, Tokyo, Japan, 2010.

[28]. Wang, Z. D.; Sheikh, S. O.; Zhang, Y. Molecules 2006, 11, 739-750.
http://dx.doi.org/10.3390/11100739

[29]. Farrugia, L. J. J. Appl. Cryst. 2012, 45, 849-854.
http://dx.doi.org/10.1107/S0021889812029111

[30]. Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; van de Streek, J. J. Appl. Cryst. 2006, 39, 453-457.
http://dx.doi.org/10.1107/S002188980600731X

[31]. Mitchell, A. G. J. Pharm. Pharmaceut. Sci. 1998, 1, 8-12.

[32]. Wilhoit, R. C.; Chan, J.; Hall, K. R. J. Phys. Chem. Ref. Data 1985, 14, 1-175.
http://dx.doi.org/10.1063/1.555747

[33]. Etter, M. C. Acc. Chem. Res. 1990, 23, 120-126.
http://dx.doi.org/10.1021/ar00172a005


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. 5 Mar. 2021
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)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



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

CrossRef | Scilit | GrowKudos | Researchgate | Publons | Microsoft | scibey | Scite | Lens | OUCI

WorldCat Paperbuzz Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



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

Refbacks

  • There are currently no refbacks.




Copyright (c)





© Copyright 2010 - 2021  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2021 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.