Skip to main content
Log in

Cobalt(II) complexes with bis-2,4-[N-(S)-phenylalanyl]-6-chlorotriazine: synthesis, structure, and application for separation of enantiomers of butan-2-ol

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The chiral coordination compounds [Co(L)(H2O)2(MeOH)] n (1) and Co2(L)2(H2O)(MeOH)4 (2) were synthesized by the reaction of bis-2,4-[N-(S)-phenylalanyl]6-chlorotriazine (LH2) with cobalt(II) pivalate or acetate. In molecules 2, the CoII ions are linked by a bridging water molecule and two carboxy groups of the L2– anion. By passing the racemate of butan-2-ol through a chromatographic column containing complex 1 as the stationary phase, a mixture enriched with the (S)-isomer of this alcohol can be obtained.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. D. Dang, P. Wu, Ch. He, Zh. Xie, Ch. Duan, J. Am. Chem. Soc., 2010, 132, 14321.

    Article  CAS  Google Scholar 

  2. Y. Liu, W. Xuan, Y. Cui, Adv. Mat., 2010, 22, 4112.

    Article  CAS  Google Scholar 

  3. M. Yoon, R. Srirambalaji, K. Kim, Chem. Rev., 2012, 112, 1196.

    Article  CAS  Google Scholar 

  4. K. Gedrich, M. Heitbaum, A. Notzon, I. Senkovska, R. Frçhlich, J. Getzschmann, U. Mueller, F. Glorius, S. Kaskel, Chem. Eur. J., 2011, 17, 2099.

    Article  CAS  Google Scholar 

  5. R. Vaidhyanathan, D. Bradshaw, J.-N. Rebilly, J. P. Barrio, J. A. Gould, N. G. Berry, M. J. Rosseinsky, Angew. Chem., Int. Ed., 2006, 45, 6495.

    Article  CAS  Google Scholar 

  6. M. C. Das, Q. Guo, Y. He, J. Kim, C.-G. Zhao, K. Hong, S. Xiang, Z. Zhang, K. M. Thomas, R. Krishna, B. Chen, J. Am. Chem. Soc., 2012, 134, 8703.

    Article  CAS  Google Scholar 

  7. M. Padmanaban, P. Müller, C. Lieder, K. Gedrich, R. Grünker, V. Bon, I. Senkovska, S. Baumgärtner, S. Opelt, S. Paasch, E. Brunner, F. Glorius, E. Klemm, S. Kaskel, Chem. Commun., 2011, 47, 12089.

    Article  CAS  Google Scholar 

  8. S.-M. Xie, Z.-J. Zhang, Z.-Y. Wang, L.-M. Yuan, J. Am. Chem. Soc., 2011, 133, 11892.

    Article  CAS  Google Scholar 

  9. A. L. Nuzhdin, D. N. Dybtsev, K. P. Bryliakov, E. P. Talsi, V. P. Fedin, J. Am. Chem. Soc., 2007, 129, 12958.

    Article  CAS  Google Scholar 

  10. C. Train, R. Gheorghe, V. Krstic, L.-M. Chamoreau, N. S. Ovanesyan, G. L. J. A. Rikken, M. Gruselle, M. Verdaguer, Nature Materials, 2008, 7, 729.

    Article  CAS  Google Scholar 

  11. E. Coronado, M. C. Giménez-Lòpez, T. Korzeniak, G. Levchenko, F. M. Romero, A. Segura, V. García-Baonza, J. C. Cezar, F. M. F. de Groot, A. Milner, M. PazPasternak, J. Am. Chem. Soc., 2008, 130, 15519.

    Article  CAS  Google Scholar 

  12. T. Wu, X.-Z. You, P. Bou, Coord. Chem. Rev., 2015, 284, 1.

    Article  CAS  Google Scholar 

  13. H.-T. Ye, C.-Y. Ren, G.-F. Hou, Y.-H. Yu, X. Xu, J.-S. Gao, P.-F. Yan, S.-W. Ng, Cryst. Growth Des., 2014, 14, 3309.

    Article  CAS  Google Scholar 

  14. S. Allenmark, Chromatographic Enantioseparation: Methods and Applications, Halsted Press/Wiley, Chichester, 1988, 224.

    Google Scholar 

  15. S.-M. Xie, X.-H. Zhang, Z.-J. Zhang, M. Zhang, J. Jia, L.-M. Yuan, Anal Bioanal Chem., 2013, 405, 3407.

    Article  CAS  Google Scholar 

  16. S.-M. Xie, X.-H. Zhang, Z.-J. Zhang, L.-M. Yuan, Anal. Lett., 2013, 46, 753.

    Article  CAS  Google Scholar 

  17. S. Xie, B. Wang, X. Zhang, J. Zhang, M. Zhang, L. Yuan, Chirality, 2014, 26, 27.

    Article  CAS  Google Scholar 

  18. D. N. Dybtsev, M. P. Yutkin, E. V. Peresypkina, A. V. Virovets, C. Serre, G. Férey, V. P. Fedin, Inorg. Chem., 2007, 46, 6843.

    Article  CAS  Google Scholar 

  19. D. N. Dybtsev, M. P. Yutkin, D. G. Samsonenko, V. P. Fedin, A. L. Nuzhdin, A. A. Bezrukov, K. P. Bryliakov, E. P. Talsi, R. V. Belosludov, H. Mizuseki, Y. Kawazoe, O. S. Subbotin, V. R. Belosludov, Chem. Eur. J., 2010, 16, 10348.

    Article  CAS  Google Scholar 

  20. D. N. Dybtsev, A. L. Nuzhdin, H. Chun, K. P. Bryliakov, E. P. Talsi, V. P. Fedin, K. Kim, Angew. Chem., Int. Ed., 2006, 45, 916.

    Article  CAS  Google Scholar 

  21. J. A. Rood, B. C. Noll, K. W. Henderson, J. Solid, State Chem., 2010, 183, 270.

    Article  CAS  Google Scholar 

  22. M. P. Yutkin, M. S. Zavakhina, D. G. Samsonenko, D. N. Dybtsev, V. P. Fedin, Russ. Chem. Bull. (Int. Ed.), 2010, 59, 733 [Izv. Akad. Nauk, Ser. Khim., 2010, 719].

    Article  CAS  Google Scholar 

  23. Z. Chen, X. Liu, C. Zhang, Z. Zhang, F. Liang, Dalton Trans., 2011, 40, 1911.

    Article  CAS  Google Scholar 

  24. N. Hoshino, M. Nakano, H. Nojiri, W. Wernsdorfer, H. Oshio, J. Am. Chem. Soc., 2009, 131, 15100.

    Article  CAS  Google Scholar 

  25. R. S. Forgan, R. A. Smaldone, J. J. Gassensmith, H. Furukawa, D. B. Cordes, Q. Li, C. E. Wilmer, Y. Y. Botros, R. Q. Snurr, A. M. Z. Slawin, J. F. Stoddart, J. Am. Chem. Soc., 2012, 134, 406.

    Article  CAS  Google Scholar 

  26. G. Li, W. Yu, J. Ni, T. Liu, Y. Liu, E. Sheng, Y. Cui, Angew. Chem., Int. Ed., 2008, 47, 1245.

    Article  CAS  Google Scholar 

  27. T. Liu, Y. Liu, W. Xuan, Y. Cui, Angew. Chem., Int. Ed., 2010, 49, 4121.

    Article  CAS  Google Scholar 

  28. T. Ezuhara, K. Endo, Y. Aoyama, J. Am. Chem. Soc., 1999, 121, 3279.

    Article  CAS  Google Scholar 

  29. G. Tian, G. Zhu, X. Yang, Q. Fang, M. Xue, J. Sun, Y. Wei, S. Qiu, Chem. Commun., 2005, 1396.

    Google Scholar 

  30. S. Wu, Y. Wu, Q. Kang, H. Zhang, L. Long, Z. Zheng, R. Huang, L. Zheng, Angew. Chem., Int. Ed., 2007, 46, 8475.

    Article  CAS  Google Scholar 

  31. S. H. Jhung, J.-H. Lee, P. M. Forster, G. Férey, A. K. Cheetham, J.-S. Chang, Chem. Eur. J., 2006, 12, 7899.

    Article  CAS  Google Scholar 

  32. V. I. Mur, Russ. Chem. Rev., 1964, 33, 92 [Usp. Khim., 1964, 33, 182].

    Article  Google Scholar 

  33. C. J. Cavallito, D. C. Schlieper, T. B. O´Dell, J. Org. Chem., 1954, 19, 826.

    Article  CAS  Google Scholar 

  34. E. A. Mikhalyova, S. V. Kolotilov, O. Cador, F. Pointillart, S. Golhen, L. Ouahab, V. V. Pavlishchuk, Inorg. Chim. Acta, 2010, 3453.

    Google Scholar 

  35. X. Zhao, H. He, T. Hu, F. Dai, D. Sun, Inorg. Chem., 2009, 48, 8057.

    Article  CAS  Google Scholar 

  36. D. Sun, S. Ma, Y. Ke, D. J. Collins, H.-C. Zhou, J. Am. Chem. Soc., 2006, 128, 3896.

    Article  CAS  Google Scholar 

  37. K. Suh, M. P. Yutkin, D. N. Dybtsev, V. P. Fedin, K. Kim, Chem. Commun., 2012, 48, 513.

    Article  CAS  Google Scholar 

  38. K. Huang, X. Dong, R. Ren, W. Jin, AIChE J., 2013, 59, 4364.

    Article  CAS  Google Scholar 

  39. P. Li, Y. He, J. Guang, L. Weng, J. C.-G. Zhao, S. Xiang, B. Chen, J. Am. Chem. Soc., 2014, 136, 547.

    Article  CAS  Google Scholar 

  40. R.-G. Xiong, X.-Z. You, B. F. Abrahams, Z. Xue, C.-M. Che, Angew. Chem., Int. Ed., 2001, 40, 4422.

    Article  CAS  Google Scholar 

  41. Yu. A. Satskaya, N. P. Komarova, K. S. Gavrilenko, O. V. Manoilenko, Zh. V. Chernenko, M. A. Kiskin, S. V. Kolotilov, I. L. Eremenko, V. M. Novotortsev, Theor. Exper. Chem., 2015, 51, 45 [Teor. Eksp. Khim., 2015, 51, 41].

    Article  Google Scholar 

  42. I. G. Fomina, G. G. Aleksandrov, Zh. V. Dobrokhotova, O. Yu. Proshenkina, M. A. Kiskin, Yu. A. Velikodnyi, V. N. Ikorskii, V. M. Novotortsev, I. L. Eremenko, Russ. Chem. Bull. (Int. Ed.), 2006, 55, 1909 [Izv. Akad. Nauk, Ser. Khim., 2006, 1841].

    Article  CAS  Google Scholar 

  43. SMART (control) and SAINT (integration) Software, Version 5.0, Bruker AXS Inc., Madison,WI, 1997.

  44. G. M. Sheldrick, SHELX-97, Program for the Refinement of Crystal Structure, University of Göttingen, Göttingen (Germany), 1997.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M. A. Kiskin.

Additional information

Dedicated to Academician of the Russian Academy of Sciences V. I. Minkin on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0630—0635, March, 2015.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Satskaya, Y.A., Komarova, N.P., Gavrilenko, K.S. et al. Cobalt(II) complexes with bis-2,4-[N-(S)-phenylalanyl]-6-chlorotriazine: synthesis, structure, and application for separation of enantiomers of butan-2-ol. Russ Chem Bull 64, 630–635 (2015). https://doi.org/10.1007/s11172-015-0910-x

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-015-0910-x

Key words

Navigation