European Journal of Chemistry 2013, 4(4), 350-352. doi:10.5155/eurjchem.4.4.350-352.872

Synthesis and crystal structure of (S)-5-isopropyl-5-methyl-2-thiohydantoin


Masaki Ichitani (1) , Soh-ichi Kitoh (2) , Keiko Tanaka (3) , Shuhei Fujinami (4) , Mitsuhiro Suda (5) , Mitsunori Honda (6) , Akio Kuwae (7) , Kazuhiko Hanai (8) , Ko-Ki Kunimoto (9,*)

(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 Sciences, Nagoya City University, Mizuho-ku, Nagoya 467-8501, Japan
(8) Graduate School of Natural Sciences, Nagoya City University, Mizuho-ku, Nagoya 467-8501, Japan
(9) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(*) Corresponding Author

Received: 11 Jul 2013, Accepted: 15 Jul 2013, Published: 31 Dec 2013

Abstract


(S)-5-Isopropyl-5-methyl-2-thiohydantoin was synthesized by one-pot reaction of α-methyl-L-valine and thiourea in the absence of solvent. The crystal structure of this compound has been determined from single crystal X-ray diffraction data. This is the first report on the crystal structure of a homochiral 5-substituted 2-thiohydantoin with the unsubstituted NH groups. This compound, C7H12N2OS crystallizes in the chiral orthorhombic space group P212121 with four molecules in the unit cell. The unit cell parameters are: a = 8.2798(12) Å, b = 8.6024(13) Å, c = 12.826(2) Å and V = 913.6(2) Å3. In the crystals, the thioamide and amide N-H of one molecule are hydrogen-bonded to the thioamide C=S group of neighboring molecules to form rings with the R22(8) graph-set motif, and these rings are linked into infinite one-dimensional tapes.

4_4_350_352

Keywords


Thiourea; Homochiral; Hydrogen-bond; Crystal structure; 2-Thiohydantoin; 2-Thioxoimidazolidin-4-one

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.4.4.350-352.872

Article Metrics


This Abstract was viewed 698 times | PDF Article downloaded 300 times

Citations

/


[1]. Masaki Ichitani, 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  5(1), 6, 2014
DOI: 10.5155/eurjchem.5.1.6-10.933
/


[2]. Gerzon E. Delgado, Luis E. Seijas, Asiloé J. Mora, Rafael Almeida, Teresa González
Crystal Structure of 2-Thiohydantoin-L-Isoleucine Synthesized under Solvent-Free Conditions
Molecular Crystals and Liquid Crystals  607(1), 192, 2015
DOI: 10.1080/15421406.2014.928433
/


References

[1]. Mutschler, E.; Derendorf, H. Drug Actions, Basic Principles and Therapeutic Aspects, Medpharm Scientific Publishers, Stuttgart, 1995.
PMCid:PMC1908869

[2]. Knabe, J.; Baldauf, J.; Ahlhem, A. Pharmazie 1997, 52, 912-919.
PMid:9480456

[3]. Singh, G.; Driever, P. H.; Sander, J. W. Brain 2005, 128, 7-17.
http://dx.doi.org/10.1093/brain/awh363
PMid:15574465

[4]. 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
PMid:16713265

[5]. Wang, Z. D.; Sheikh, S. O.; Zhang, Y. Molecules 2006, 11, 739-750.
http://dx.doi.org/10.3390/11100739
PMid:17971750

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

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

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

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

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

[11]. Ogawa, T.; Okumura, H.; Honda, M.; Suda, M.; Fujinami, S.; Kuwae, A.; Hanai, K.; Kunimoto, K. K. Anal. Sci. X-ray Struct. Anal. Online 2009, 25, 91-92.
http://dx.doi.org/10.2116/xraystruct.25.91

[12]. Taniguchi, K.; Okumura, H.; Honda, M.; Suda, M.; Fujinami, S.; Kuwae, A.; Hanai, K.; Maeda, S.; Kunimoto, K. K. Anal. Sci. X-ray Struct. Anal. Online 2009, 25, 93-94.
http://dx.doi.org/10.2116/xraystruct.25.93

[13]. Ichitani, M.; Kitoh, S.; Fujinami, S.; Honda, M.; Suda, M.; Kunimoto, K. K. Acta Cryst. E 2013, 69, o953-o953.
http://dx.doi.org/10.1107/S1600536813013639
PMid:23795113 PMCid:PMC3685094

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

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

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

[17]. Sheldrick, G. M. Acta Crystallogr. A 2008, 64, 112-122.
http://dx.doi.org/10.1107/S0108767307043930
PMid:18156677

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

[19]. Flack, H. D. Acta Crystallogr. A 1983, 39, 876-881.
http://dx.doi.org/10.1107/S0108767383001762

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

[21]. 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

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


How to cite


Ichitani, M.; Kitoh, S.; Tanaka, K.; Fujinami, S.; Suda, M.; Honda, M.; Kuwae, A.; Hanai, K.; Kunimoto, K. Eur. J. Chem. 2013, 4(4), 350-352. doi:10.5155/eurjchem.4.4.350-352.872
Ichitani, M.; Kitoh, S.; Tanaka, K.; Fujinami, S.; Suda, M.; Honda, M.; Kuwae, A.; Hanai, K.; Kunimoto, K. Synthesis and crystal structure of (S)-5-isopropyl-5-methyl-2-thiohydantoin. Eur. J. Chem. 2013, 4(4), 350-352. doi:10.5155/eurjchem.4.4.350-352.872
Ichitani, M., Kitoh, S., Tanaka, K., Fujinami, S., Suda, M., Honda, M., Kuwae, A., Hanai, K., & Kunimoto, K. (2013). Synthesis and crystal structure of (S)-5-isopropyl-5-methyl-2-thiohydantoin. European Journal of Chemistry, 4(4), 350-352. doi:10.5155/eurjchem.4.4.350-352.872
Ichitani, Masaki, Soh-ichi Kitoh, Keiko Tanaka, Shuhei Fujinami, Mitsuhiro Suda, Mitsunori Honda, Akio Kuwae, Kazuhiko Hanai, & Ko-Ki Kunimoto. "Synthesis and crystal structure of (S)-5-isopropyl-5-methyl-2-thiohydantoin." European Journal of Chemistry [Online], 4.4 (2013): 350-352. Web. 21 Oct. 2019
Ichitani, Masaki, Kitoh, Soh-ichi, Tanaka, Keiko, Fujinami, Shuhei, Suda, Mitsuhiro, Honda, Mitsunori, Kuwae, Akio, Hanai, Kazuhiko, AND Kunimoto, Ko-Ki. "Synthesis and crystal structure of (S)-5-isopropyl-5-methyl-2-thiohydantoin" European Journal of Chemistry [Online], Volume 4 Number 4 (31 December 2013)

DOI Link: https://doi.org/10.5155/eurjchem.4.4.350-352.872

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2019  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 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.