Russian Chemical Bulletin

, Volume 68, Issue 8, pp 1575–1579 | Cite as

Synthesis and structure of new anionic five-coordinate silicon complexes derived from α-hydroxy acids and 1-methylpiperazine-2,5-dione

  • A. A. NikolinEmail author
  • A. A. Korlyukov
  • E. P. Kramarova
  • D. E. Arkhipov
  • A. G. Shipov
  • Yu. I. Baukov
  • Vad. V. Negrebetskii
Full Article


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.

Key words

five-coordinate silicon compounds anionic complexes X-ray diffraction 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    T. Rezanka, K. Sigler, Studies in Natural Products Chemistry, 2008, 35, 856.Google Scholar
  2. 2.
    M. G. Voronkov, G. I. Zelgan, E. Ya. Lukevits, Kremnii i Zhizn. [Silicon and Life], Zinatne, Riga, 1978, 587 pp. (in Russian).Google Scholar
  3. 3.
    E. Lukevics, E. Abele, L. Ignatovich, Adv. Heterocycl. Chem., 2010, 99, 107.CrossRefGoogle Scholar
  4. 4.
    V. V. Negrebetsky, S. N. Tandura, Yu. I. Baukov, Russ. Chem. Rev., 2009, 78, 21.CrossRefGoogle Scholar
  5. 5.
    Cambridge Structural Database System, Release 1.19, Version 5.39, 2017.Google Scholar
  6. 6.
    R. Tacke, O. Dannappel, M. Muhleisen, Organosilicon Chemistry, II, Wiley Blackwell, 2008, p. 427–446.Google Scholar
  7. 7.
    A. A. Nikolin, V. V. Negrebetsky, Russ. Chem. Rev., 2014, 83, 848].CrossRefGoogle Scholar
  8. 8.
    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.CrossRefGoogle Scholar
  9. 9.
    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.CrossRefGoogle Scholar
  10. 10.
    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.CrossRefGoogle Scholar
  11. 11.
    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.Google Scholar
  12. 12.
    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).Google Scholar
  13. 13.
    R. R. Holmes, J. A. Deiters, J. Am. Chem. Soc., 1977, 99, 3318.CrossRefGoogle Scholar
  14. 14.
    G. M. Sheldrick, Acta Cryst., 2015, A71, 3.Google Scholar
  15. 15.
    O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Cryst., 2009, 42, 339.CrossRefGoogle Scholar
  16. 16.
    P. A. Levene, H. S. Simms, M. H. Pflats, J. Biol. Chem., 1924, 61, 445.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2019

Authors and Affiliations

  • A. A. Nikolin
    • 1
    Email author
  • A. A. Korlyukov
    • 1
    • 2
  • E. P. Kramarova
    • 1
  • D. E. Arkhipov
    • 2
  • A. G. Shipov
    • 1
  • Yu. I. Baukov
    • 2
  • Vad. V. Negrebetskii
    • 1
  1. 1.N. I. Pirogov Russian National Research Medical UniversityMoscowRussian Federation
  2. 2.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

Personalised recommendations