Abstract
Nickel(ii) complexes were synthesized using chiral N-thiophosphorylated thioureas as the starting compounds and 4-dimethylaminopyridine as a co-ligand. The reaction with racemic thiourea afforded homochiral complexes due to the distortion of the nickel coordination. The unsaturated coordination sphere of nickel ions results in the formation of supramolecular homochiral 1D chains in the crystal through steric key—lock interactions between adjacent molecules. Conformational flexibility of the ligands is responsible for disorder of molecules in the crystals and the occurrence of polymorphs.
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References
Chiral Recognition in Separation Methods, Ed. A. Berthod, Springer-Verlag, Berlin, 2010, 337 p.
The Origin of Chirality in the Molecules of Life: A Revision from Awareness to the Current Theories and Perspectives of this Unsolved Problem, Eds A. Guijarro, M. Yus, Royal Society of Chemistry, Cambridge, 2009, 150 pp.
K. Soai, Proc. Jpn. Acad., Ser. B, 2019, 95, 89; DOI: https://doi.org/10.2183/pjab.95.009.
Y. Sang, M. Liu, Symmetry, 2019, 11, 950; DOI: https://doi.org/10.3390/sym11080950.
A. J. Bissette, S. P. Fletcher, Angew. Chem., Int. Ed. Engl., 2013, 52, 12800; DOI: https://doi.org/10.1002/anie.201303822.
D. G. Blackmond, Phil. Trans. R. Soc. B, 2011, 366, 2878; DOI: https://doi.org/10.1098/rstb.2011.0130.
M. Quack, Angew. Chem. Int. Ed. Engl., 2002, 41, 4618; DOI: https://doi.org/10.1002/anie.200290005.
K. Soai, S. Niwa, H. Hori, J. Chem. Soc. Chem. Commun., 1990, 982; DOI: https://doi.org/10.1039/C39900000982.
F. C. Frank, Biochim. Biophys. Acta, 1953, 11, 459; DOI: https://doi.org/10.1016/0006-3002(53)90082-1.
Enantioselection in Asymmetric Catalysis, Eds I. D. Gridnev, P. A. Dub, CRC Press, Boca Raton, 2016, 246 p.
J. F. Scholtes, O. Trapp, Angew. Chem. Int. Ed. (Engl.), 2019, 58, 6306; DOI: https://doi.org/10.1002/anie.201901175.
Y. Li, X. Caumes, M. Raynal, L. Bouteiller, Chem. Commun., 2019, 55, 2162; DOI: https://doi.org/10.1039/C8CC09819K.
C. Tan, D. Chu, X. Tang, Y. Liu, W. Xuan, Y. Cui, Chem. Eur. J., 2019, 25, 662; DOI: https://doi.org/10.1002/chem.201802817.
A. Gualandi, F. Calogero, S. Potenti, P. G. Cozzi, Molecules, 2019, 24, 1716; DOI: https://doi.org/10.3390/molecules24091716.
M. Durmaz, E. Halay, S. Bozkurt, Beil. J. Org. Chem., 2018, 14, 1389; DOI: https://doi.org/10.3762/bjoc.14.117.
Z. Xia, X. Jing, C. He, X. Wang, C. Duan, Sci. Rep., 2017, 7, 15418; DOI: https://doi.org/10.1038/s41598-017-15780-0.
Chiral Separations: Methods and Protocols, Ed. G. K. E. Scriba, Humana Press, New York, 2019, 501 p.
A. Singh, N. Kaur, H. Kumar Chopra, Crit. Rev. Anal. Chem., 2019, 49, 553; DOI: https://doi.org/10.1080/10408347.2019.1565985.
X. Deng, W. Li, G. Ding, T. Xue, X. Chen, Sep. Purif. Rev., 2019, 48, 14; DOI: https://doi.org/10.1080/15422119.2017.1419257.
X.-Y. Huang, K.-J. Quan, D. Pei, J.-F. Liu, D.-L. Di, Chirality, 2018, 30, 974; DOI: https://doi.org/10.1002/chir.22975.
M. Greño, M. L. Marina, M. Castro-Puyana, Crit. Rev. Anal. Chem., 2018, 48, 429; DOI: https://doi.org/10.1080/10408347.2018.1439365.
M. Rachwalski, N. Vermue, F. P. J. T. Rutjes, Chem. Soc. Rev., 2013, 42, 9268; DOI: https://doi.org/10.1039/C3CS60175G.
A. Berthod, Anal. Chem., 2006, 78, 2093; DOI: https://doi.org/10.1021/ac0693823.
D. Braga, F. Grepioni, L. Maini, S. d’Agostino, IUCrJ, 2017, 4, 369; DOI: https://doi.org/10.1107/S2052252517005917.
G. R. Desiraju, J. Am. Chem. Soc., 2013, 135, 9952; DOI: https://doi.org/10.1021/ja403264c.
J. McConathy, M. J. Owens, Prim. Care Companion J. Clin. Psychiatry, 2003, 5, 70; DOI: https://doi.org/10.4088/pcc.v05n0202.
O. N. Kataeva, K. E. Metlushka, Z. R. Yamaleeva, K. A. Ivshin, A. G. Kiiamov, O. A. Lodochnikova, K. A. Nikitina, D. N. Sadkova, L. N. Punegova, A. D. Voloshina, A. P. Lyubina, A. S. Sapunova, O. G. Sinyashin, V. A. Alfonsov, Cryst. Growth Des., 2019, 19, 4044; DOI: https://doi.org/10.1021/acs.cgd.9b00446.
O. Kataeva, K. Metlushka, Z. Yamaleeva, K. Ivshin, R. Zinnatullin, K. Nikitina, D. Sadkova, E. Badeeva, O. Sinyashin, V. Alfonsov, Crystals, 2019, 9, 606; DOI: https://doi.org/10.3390/cryst9120606.
K. E. Metlushka, D. N. Sadkova, L. N. Shaimardanova, K. A. Nikitina, K. A. Ivshin, D. R. Islamov, O. N. Kataeva, A. V. Alfonsov, V. E. Kataev, A. D. Voloshina, L. N. Punegova, V. A. Alfonsov, Inorg. Chem. Commun., 2016, 66, 11; DOI: https://doi.org/10.1016/j.inoche.2016.01.021.
K. E. Metlushka, D. N. Sadkova, K. A. Nikitina, O. A. Lodochnikova, O. N. Kataeva, V. A. Alfonsov, Russ. J. Gen. Chem., 2017, 87, 2130; DOI: https://doi.org/10.1134/S1070363217090389.
M. G. Babashkina, D. A. Safin, M. Srebro, P. Kubisiak, M. P. Mitoraj, M. Bolte, Y. Garcia, Eur. J. Inorg. Chem., 2013, 545; DOI: https://doi.org/10.1002/ejic.201200890.
M. G. Babashkina, D. A. Safin, M. Srebro, P. Kubisiak, M. P. Mitoraj, M. Bolte, Y. Garcia, CrystEngComm, 2011, 13, 5321; DOI: https://doi.org/10.1039/c1ce05387f.
M. G. Babashkina, D. A. Safin, M. Bolte, M. Srebro, M. Mitoraj, A. Uthe, A. Klein, M. Köckerling, Dalton Trans., 2011, 40, 3142; DOI: https://doi.org/10.1039/c0dt01382j.
Bruker. APEX3 Crystallography Software Suite, Bruker AXS Inc., Bruker, Area Detector Control and Integration Software, Version 5.x, in SMART, Madison, WI, USA, 2016.
Bruker. SAINT Crystallography Software Suite, Bruker AXS Inc., Madison, WI, USA, 2016.
L. Krause, R. Herbst-Irmer, G. M. Sheldrick, D. Stalke, J. Appl. Crystallogr., 2015, 48, 3; DOI: https://doi.org/10.1107/S1600576714022985.
G. M. Sheldrick, Acta Crystallogr. Sect. A, 2008, 64, 112; DOI: https://doi.org/10.1107/S0108767307043930.
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Based on the materials of the II Scientific Conference “Dynamic Processes in the Chemistry of Organoelement Compounds” (November 11–13, 2020, Kazan, Russia).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1304–1310, July, 2021.
This study was financially supported by the Russian Foundation for Basic Research (Project No. 20-03-00572) and a subsidy allocated to the Kazan Federal University for the implementation of the state assignment in the field of scientific activity (Project No. 0671-2020-0063).
We gratefully acknowledge the Spectral-Analytical Center of the Federal Research Center of Kazan Scientific Center of Russian Academy of Sciences (CSF-SAC FRC KSC RAS) for providing necessary facilities to carry out this work.
This paper does not contain descriptions of studies on animals or humans.
The authors declare no competing interests.
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Metlushka, K.E., Sadkova, D.N., Nikitina, K.A. et al. Chiral recognition of N-thiophosphorylated thioureas via nickel(ii) coordination assisted by 4-dimethylaminopyridine. Russ Chem Bull 70, 1304–1310 (2021). https://doi.org/10.1007/s11172-021-3215-2
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DOI: https://doi.org/10.1007/s11172-021-3215-2