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Chiral resolution of l- and d-alanine and a racemic macrocyclic nickel(II) complex: synthesis and crystal structures

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Abstract

The reactions of a racemic four-coordinate Ni(II) complex [Ni(rac-L)](ClO4)2 with l- and d-alanine in acetonitrile/water gave two six-coordinate enantiomers formulated as [Ni(RR-L)(l-Ala)](ClO4)·2CH3CN (1) and [Ni(SS-L)(d-Ala)](ClO4) (2) (L = 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclo-tetradecane, Ala− = alanine anion), respectively. Evaporation from the remaining solutions gave two four-coordinate enantiomers characterized as [Ni(SS-L)](ClO4)2 (S-3) and [Ni(RR-L)](ClO4)2 (R-3), respectively. Single-crystal X-ray diffraction analyses of complexes 1 and 2 revealed that the Ni(II) atom has a distorted octahedral coordination geometry, being coordinated by four nitrogen atoms of L in a folded configuration, plus one carboxylate oxygen atom and one nitrogen atom of l- or d-Ala− in mutually cis-positions. Complexes 1 and 2 are supramolecular stereoisomers, constructed via hydrogen bonding between [Ni(RR-L)(l-Ala)]+ or [Ni(SS-L)(d-Ala)]+ monomers to form 1D hydrogen-bonded zigzag chains. The homochiral natures of complexes 1 and 2 have been confirmed by CD spectroscopy.

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References

  1. Afonso CAM, Crespo JG (2004) Angew Chem Int Ed 43:5293

    Article  CAS  Google Scholar 

  2. Xie R, Chu LY, Deng JG (2008) Chem Soc Rev 37:1243

    Article  CAS  Google Scholar 

  3. Wong MM, Holzheuer WB, Webster GK (2008) Curr Pharm Anal 4:101

    Article  CAS  Google Scholar 

  4. Lourenco NMT, Afonso CAM (2007) Angew Chem Int Ed 46:8178

    Article  CAS  Google Scholar 

  5. Yang M, Chu LY, Wang HD, Xie R, Song H, Niu CH (2008) Adv Funct Mater 18:652

    Article  Google Scholar 

  6. Yang PX, Xu RF, Nanita SC, Cooks RG (2006) J Am Chem Soc 128:17074

    Article  CAS  Google Scholar 

  7. Klussmann M, Iwamura H, Mathew SP, Wells DH, Pandya JU, Armstrong A, Blackmond DG (2006) Nature 441:621

    Article  CAS  Google Scholar 

  8. Pizzarello S, Weber AL (2004) Science 303:1151

    Article  CAS  Google Scholar 

  9. Mathew SP, Iwamura H, Blackmond DG (2004) Angew Chem Int Ed 43:3317

    Article  CAS  Google Scholar 

  10. Imai Y, Kawaguchi T, Tajima N, Sato T, Kuroda R, Matsubara Y (2008) Chem Commun 3:362

  11. Gao MJ, Yang P, Cai B (2012) CrystEngComm 14:1264

    Article  CAS  Google Scholar 

  12. Liu GN, Lin JD, Xu ZN (2011) Cryst Growth Des 11:3318

    Article  CAS  Google Scholar 

  13. Teng YL, Dong BX, Peng J (2013) CrystEngComm 15:2783

    Article  CAS  Google Scholar 

  14. Wu ST, Wu YR, Kang QQ, Zhang H, Long LS, Zheng ZP, Huang RB, Zheng LS (2007) Angew Chem Int Ed 46:8475

    Article  CAS  Google Scholar 

  15. Hou Y, Fang XK, Hill CL (2007) Chem Eur J 13:9442

    Article  CAS  Google Scholar 

  16. Xuan WM, Zou F, Chen LQ, Fang XM, Lian W, Zhang H (2008) Acta Phys Chim Sin 24:955

    CAS  Google Scholar 

  17. Zhao L, Wan SG, Chen CD, Lin YJ, Fang XM, Zhang H (2013) Acta Phys Chim Sin 29:1183

    Google Scholar 

  18. Kang SH, Shan SC, Noorduin WL (2013) Adv Mater 25:3380

    Article  CAS  Google Scholar 

  19. Ou GC, Jiang L, Feng XL, Lu TB (2008) Inorg Chem 47:2710

    Article  CAS  Google Scholar 

  20. Ou GC, Wang ZZ, Yang LZ, Zhao CY, Lu TB (2010) Dalton Trans 39:4274

    Article  CAS  Google Scholar 

  21. Ou GC, Yuan XY, Jiang XP (2011) Transition Met Chem 36:189

    Article  CAS  Google Scholar 

  22. Ou GC, Yuan XY, Li ZZ (2013) Z Anorg Allg Chem 639:158

    Article  CAS  Google Scholar 

  23. Curtis NF (1960) J Chem Soc (A) 4409

  24. Tait AM, Busch DH (1967) Inorg Synth 18:4

    Google Scholar 

  25. Jiang L, Feng XL, Lu TB (2005) Cryst Growth Des 5:1469

    Article  CAS  Google Scholar 

  26. Sheldrick GM (1996) SADABS, program for empirical absorption correction of area detector data. University of Göttingen, Göttingen

    Google Scholar 

  27. Sheldrick GM (1997) SHELXS 97, program for crystal structure refinement. University of Göttingen, Göttingen

    Google Scholar 

  28. Clark TD, Ghadiri MR (1995) J Am Chem Soc 117:12364

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Scientific Research Fund of Hunan Provincial Education Department (13B029, 13A030, 13CY029), the Program for Excellent Talents in Hunan University of Science and Engineering, the Construct Program of the Key Discipline in Hunan Province (2011-76), the Science and Technology Innovative Research Team in Higher Educational Institutions of Hunan Province (2012-318) and NSF of Hunan (11JJ2009).

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Authors and Affiliations

  1. Department of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou, 425199, Hunan, People’s Republic of China

    Guang-Chuan Ou, Zhi-Zhang Li, Min Zhang & Xian-You Yuan

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  1. Guang-Chuan Ou
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  2. Zhi-Zhang Li
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  3. Min Zhang
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Correspondence to Guang-Chuan Ou.

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Ou, GC., Li, ZZ., Zhang, M. et al. Chiral resolution of l- and d-alanine and a racemic macrocyclic nickel(II) complex: synthesis and crystal structures. Transition Met Chem 39, 135–140 (2014). https://doi.org/10.1007/s11243-013-9782-9

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