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BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access December 23, 2008

Structure, conformation and hydrogen bonding of two amino-cycloalkanespiro-5-hydantoins

Petar Todorov, Rosica Petrova, Emilia Naydenova and Boris Shivachev
From the journal Open Chemistry

Abstract

The crystal structures of 3-amino-cycloheptanespiro-4′-imidazolidine-2′,5′-dione (I) {systematic name: 3-amino-1,3-diazaspiro[4.6] undecane-2,4-dione} and 3-amino-cyclooctanespiro-4′-imidazolidine-2′,5′-dione (II) {systematic name: 3-amino-1,3-diazaspiro[4.7] dodecane-2,4-dione}, have been determined. In both compounds the polar hydantoin groups cause molecules to aggregate via N-H...O and N-H...N interactions, forming a layer structure, in which the cycloalkane rings project outwards from the central, more polar, region. The observed molecular structure is compared with that calculated by density functional theory methods.

[1] A.C. Lopez, C.G. Trigo, Advances in Heterocyclic Chemistry; A. R. Katritzky, Ed. (Academic Press, New York, 1985) 177 10.1016/S0065-2725(08)60920-4Search in Google Scholar

[2] S. Scholl, A. Koch, D. Henning, G. Kempter, E. Kleinpeter, Struct. Chem. 10, 355 (1999) http://dx.doi.org/10.1023/A:102209141101810.1023/A:1022091411018Search in Google Scholar

[3] K. H. Park, M.M. Olmstead, M.J. Kurth, J. Org. Chem. 63, 113 (1998) http://dx.doi.org/10.1021/jo971483110.1021/jo9714831Search in Google Scholar

[4] L. Somsak, V. Nagy, Z. Hadady, N. Felfold, T. Docsa, P. Gergely, Frontiers in Med. Chem. 2, 253 (2005) 10.2174/1567204052930907Search in Google Scholar

[5] E. Naydenova, N. Pencheva, J. Popova, N. Stoyanov, M. Lazarova, B. Aleksiev, Il Farmaco 57, 189 (2002) http://dx.doi.org/10.1016/S0014-827X(01)01198-310.1016/S0014-827X(01)01198-3Search in Google Scholar

[6] D. Kushev, G. Gorneva, V. Enchev, E. Naydenova, J. Popova, S. Taxirov, L. Maneva, K. Grancharov, N. Spassovska, J. Inorg. Biochem. 89, 203 (2002) http://dx.doi.org/10.1016/S0162-0134(01)00420-210.1016/S0162-0134(01)00420-2Search in Google Scholar

[7] B. Shivachev, R. Petrova, E. Naydenova, Acta Cryst. C 61, 524 (2005) http://dx.doi.org/10.1107/S010827010501603310.1107/S0108270105016033Search in Google Scholar PubMed

[8] M.J. Frisch et al., Gaussian 03, Revision C.01 (Wallingford, CT, 2004) Search in Google Scholar

[9] A.D. Becke, Phys. Rev. A38, 3098 (1988) 10.1103/PhysRevA.38.3098Search in Google Scholar

[10] A.D. Becke, J. Chem. Phys. 98, 5648 (1993) http://dx.doi.org/10.1063/1.46491310.1063/1.464913Search in Google Scholar

[11] C. Lee, W. Yang, R.G. Parr, Phys. Rev. B37, 785 (1988) 10.1103/PhysRevB.37.785Search in Google Scholar

[12] W. J. Hehre, L. Random, P. v R. Schleyer, J.A. Pople, Ab Initio Molecular Orbital Theory (Wiley, New York, 1986) Search in Google Scholar

[13] G. M. Sheldrick, Acta Cryst. A64, 112 (2008) 10.1107/S0108767307043930Search in Google Scholar

[14] E. Benedetti, B. Di Blasio, R. Iacovino, V. Menchise, M. Saviano, C. Pedone, G.M. Bonora A. Ettorre, L. Graci, F. Formaggio, M. Crisma, G. Valle, C. Toniolo. J.Chem. Soc., Perkin Trans. 2, 2023 (1997) http://dx.doi.org/10.1039/a701473b10.1039/a701473bSearch in Google Scholar

[15] R.W. Miller, A.T. McPhail. J. Chem. Res. 330, 3831 (1979) Search in Google Scholar

[16] F-L. Yu, C. H. Schwalbea, D. J. Watkinb, Acta Cryst. C60, o714 (2004) 10.1107/S0108270104017706Search in Google Scholar

[17] A. Entrena, J. M. Campos, M. A. Gallo, A. Espinosa, ARKIVOC vi 88 (2005) 10.3998/ark.5550190.0006.608Search in Google Scholar

[18] B. Shivachev, R. Petrova, P. Marinova, N. Stoyanov, A. Ahmedova, M. Mitewa, Acta Cryst. C62, 211 (2006) 10.1107/S0108270106003489Search in Google Scholar

[19] J. Perez, K. Nolsoe, M. Kessler, L. Garcia, E. Perez, J.L. Serrano, Acta Cryst. B61, 585 (2005) Search in Google Scholar

[20] S. Cortes, Z.-K. Liao, D. Watson, H. Kohn, J. Med. Chem. 28, 601 (1985) http://dx.doi.org/10.1021/jm50001a01210.1021/jm50001a012Search in Google Scholar

[21] E. Kleinpeter, M. Heydenreich, L. Kalder, A. Koch, D. Henning, G. Kempter, R. Benassi, F. Taddei, J. Mol. Struct. 403, 111 (1997) http://dx.doi.org/10.1016/S0022-2860(96)09403-310.1016/S0022-2860(96)09403-3Search in Google Scholar

Published Online: 2008-12-23
Published in Print: 2009-3-1

© 2009 Versita Warsaw

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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