Abstract
Anionic five-coordinate complexes with two bis-O,O’-chelating ligands bearing α-hydroxy acid moieties, dicyclohexylammonium salts \(\text{Cy}_{2}\text{NH}_{2}{^+}\{\text{PpnCH}_2\text{Si}[\text{OCR}_2\text{C}\text{(O)O]}_2\}^-\) (Cy is cyclohexyl, PpnCH2 is 4-methyl-2,5-dioxopiperazin-1-ylmethyl, R = Me, Ph), were synthesized by esterification of alkoxysilane PpnCH2Si(OMe)3 with α-hydroxy acids (dimethyl- and diphenylgylcolic acids) in the presence of dicyclohexylamine. The five-coordinated state of the silicon atom in the resulting compounds in solution was confirmed by 29Si NMR spectroscopy. According to the X-ray diffraction data, the synthesized compounds contain the SiCO4 coordination unit.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
T. Rezanka, K. Sigler, Studies in Natural Products Chemistry, 2008, 35, 856.
M. G. Voronkov, G. I. Zelgan, E. Ya. Lukevits, Kremnii i Zhizn. [Silicon and Life], Zinatne, Riga, 1978, 587 pp. (in Russian).
E. Lukevics, E. Abele, L. Ignatovich, Adv. Heterocycl. Chem., 2010, 99, 107.
V. V. Negrebetsky, S. N. Tandura, Yu. I. Baukov, Russ. Chem. Rev., 2009, 78, 21.
Cambridge Structural Database System, Release 1.19, Version 5.39, 2017.
R. Tacke, O. Dannappel, M. Muhleisen, Organosilicon Chemistry, II, Wiley Blackwell, 2008, p. 427–446.
A. A. Nikolin, V. V. Negrebetsky, Russ. Chem. Rev., 2014, 83, 848].
S. Yu. Bylikin, A. G. Shipov, E. P. Kramarova, Vad. V. Negrebetsky, A. A. Korlyukov, Yu. I. Baukov, M. B. Hursthouse, L. Male, A. Bassindale, P. Taylor, J. Organometal. Chem., 2009, 694, 244.
A. G. Shipov, A. A. Korlyukov, E. P. Kramarova, D. E. Arkhipov, S. Yu. Bylikin, Huntse Fan, S. A. Pogozhikh, T. P. Murasheva, V. V. Negrebetskii, V. N. Khrustalev, Yu. E. Ovchinnikov, A. R. Bassindale, P. G. A. Taylor, Yu. I. Baukov, Russ. J. Gen. Chem.. 2011, 81, 2412.
A. G. Shipov, A. A. Korlyukov, D. E. Arkhipov, E. P. Kramarova, V. V. Negrebetsky, S. Yu. Bylikin, A. A. Nikolin, Huntse Fan, M. Yu. Antipin, Y. I. Baukov, Mendeleev Commun., 2010, 20, 273.
A. I. Albanov, M. F. Larin, V. A. Pestunovich, M. G. Voronkov, E. P. Kramarova, Yu. I. Baukov, J. Gen. Chem. USSR, 1981, 51, 488.
A. A. Nikolin, S. I. Krupina, D. E. Arkhipov, A. A. Nikolin, A. A. Korlyukov, A. N. Shkoporov, A. G. Shipov L. I. Kafarskaya, Yu. I. Baukov, V. V. Negrebetskii, Vestn. RGMU [Bull. RSMU], 2012, 70 (in Russian).
R. R. Holmes, J. A. Deiters, J. Am. Chem. Soc., 1977, 99, 3318.
G. M. Sheldrick, Acta Cryst., 2015, A71, 3.
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Cryst., 2009, 42, 339.
P. A. Levene, H. S. Simms, M. H. Pflats, J. Biol. Chem., 1924, 61, 445.
Author information
Authors and Affiliations
Corresponding author
Additional information
Deceased.
Rights and permissions
About this article
Cite this article
Nikolin, A.A., Korlyukov, A.A., Kramarova, E.P. et al. Synthesis and structure of new anionic five-coordinate silicon complexes derived from α-hydroxy acids and 1-methylpiperazine-2,5-dione. Russ Chem Bull 68, 1575–1579 (2019). https://doi.org/10.1007/s11172-019-2595-z
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-019-2595-z