Skip to main content
SpringerLink
Log in

Synthesis and Structure of a Host-Guest Inclusion System Between C-iso-butyl-calix[4]methyl-resorcinarene and 1-propyl-pyrrolidine-2-carboxylic acid

  • Brief Communication
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

Self-assembly of the bowl-shaped cavitand C-iso-butyl-calix[4]methyl-resorcinarene (1) with the bifunctional amino acid 1-propyl-pyrrolidine-2-carboxylic acid (2) in methanol afforded a host‒guest 2:2 complex 3, whose structure was determined by single crystal X-ray diffraction. Complex 3 crystallizes in the monoclinic space group P21, with a = 12.319(5) Å, b = 37.968(15) Å, c = 12.900(5) Å, α = 90°, β = 112.946(5)°, γ = 90°, and Z = 2. Amino acid molecules sit inside the resorcinarene cavitands via intermolecular O‒H⋯O hydrogen bonding in complex 3.

Graphical Abstract

Self-assembly of the bowl-shaped C-iso-butyl-calix[4]methyl-resorcinarene with bifunctional 1-propyl-pyrrolidine-2-carboxylic acid was investigated.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2

References

  1. Selkti M, Tomas A, Coleman AW, Douteau-Guével N, Nicolis I, Villain F (2000) Chem Commun 161–162

  2. Zhang M, Yan X, Huang F, Niu Z, Gibson HW (2014) Acc Chem Res 47:1995–2005

    Article  CAS  Google Scholar 

  3. Yang X, Yuan D, Hou J, Sedgwick AC, Wang L (2021) Coord Chem Rev 428:213609–213623

    Article  CAS  Google Scholar 

  4. Zhang Q, Catti L, Tiefenbacher K (2018) Acc Chem Res 51:2107–2114

    Article  CAS  Google Scholar 

  5. Pei W-Y, Yang J, Wu H, Zhou W, Yang Y-W, Ma J-F (2020) ) Chem Commun 56:2491–2494

    Article  CAS  Google Scholar 

  6. Twum K, Rautiainen JM, Yu S, Truong KN, Feder J, Rissanen K, Puttreddy R, Beyeh NK (2020) Cryst Growth Des 20(4):2367–2376

    Article  CAS  Google Scholar 

  7. Baeyer A (1872) Berichte der deutschen chemischen Gesellschaft 5(2):1094–1100

    Article  Google Scholar 

  8. Erdtman H, Högberg S (1968) Tetrahedron Lett 9(14):1679–1682

    Article  Google Scholar 

  9. Sakano T, Ohashi T, Yamanaka M, Kobayashi K (2015) Org Biomol Chem 13:8359–8364

    Article  CAS  Google Scholar 

  10. Togari Y, Hirota S, Kitagawa H, Tsukamoto Y, Kobayashi K (2018) Org Biomol Chem 16(41):7626–7635

    Article  CAS  Google Scholar 

  11. Velásquez-Silva A, Forero RS, Sanabria E, Pérez-Redondo A, Maldonado M (2019) J Mol Struct 1198:126846–126852

    Article  CAS  Google Scholar 

  12. Ikeda A, Shinkai S (1997) Chem Rev 97:1713–1734

    Article  CAS  Google Scholar 

  13. Kane CM, Ugono O, Barbour LJ, Holman KT (2015) Chem Mater 27:7337–7354

    Article  CAS  Google Scholar 

  14. Rakesh P, Kodiah BN, Maryamdokht TS, Daniel M, Trant JF, Kari R (2018) Beilstein J Org Chem 14:1723–1733

    Article  CAS  Google Scholar 

  15. Giust S, Sorella GL, Sperni L, Strukul G, Scarso A (2015) Chem Commun 51:1658–1661

    Article  CAS  Google Scholar 

  16. Fujisawa I, Kitamura Y, Kato R, Murayama K, Aoki K (2014) J Mol Struct 1056-1057:292–298

    Article  CAS  Google Scholar 

  17. Liu J-L, Liu X-L, Jia A-Q, Shi H-T, Zhang Q-F (2020) J Incl Phenom Macrocycl Chem 98:49–56

    Article  CAS  Google Scholar 

  18. Liu X-L, Liu J-L, Wang N-N, Jia A-Q, Zhang Q-F (2020) Inorg Nano-Met Chem 50((12):):1315–1321

    Article  CAS  Google Scholar 

  19. Liu X-L, Liu J-L, Yang H-M, Jia A-Q, Zhang Q-F (2021) J Chem Crystallogr 51:139–144

    Article  CAS  Google Scholar 

  20. Wang Y-J, Liu J-L, Yang H-M, Jia A-Q, Zhang Q-F (2016) J Incl Phenom Macrocycl Chem 85:105–110

    Article  CAS  Google Scholar 

  21. Cram DJ, Karbach S, Kim HE, Knobler CB, Maverick EF, Ericson JL, Helgeson RC (1988) J Am Chem Soc 110:2229–2237

    Article  CAS  Google Scholar 

  22. Wein T, Petrera M, Allmendinger L, Höfner G, Pabel J, Wanner KT (2016) ChemMedChem 11:509–518

    Article  CAS  Google Scholar 

  23. SMART and SAINT+ for Windows NT Version 6.02a (1988) Bruker analytical X-ray instruments Inc., Madison, Wisconsin, USA

  24. Sheldrick GM (1996) SADABS. University of Göttingen, Germany

    Google Scholar 

  25. Sheldrick GM (1997) SHELXTL Software Reference Manual. Version 5.1. Bruker AXS Inc., Madison

    Google Scholar 

  26. Sheldrick GM (2008) Acta Crystallogr A 64:112–122

    Article  CAS  Google Scholar 

  27. Pinalli R, Brancatelli G, Pedrini A, Menozzi D, Hernandez D, Ballester P (2016) J Am Chem Soc 138(27):8569–8580

    Article  CAS  Google Scholar 

  28. Aoki K, Fujisawa I, Harima N, Takagi K, Hiraoka S, Shionoya M, Murayama K (2012) ) B Chem Soc Jpn 85(9):1037–1039

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This project was supported by Natural Science Foundation of Universities of Anhui Province (Grant No. KJ2019A0060).

Author information

Authors and Affiliations

  1. Institute of Molecular Engineering and Applied Chemistry, Anhui University of Technology, Ma’anshan, 243002, Anhui, People’s Republic of China

    Yan-Hui Shi, Yu-Rou Jiang, Jing-Long Liu, Pei-Zhi Zhang, Ai-Quan Jia & Qian-Feng Zhang

Authors
  1. Yan-Hui Shi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu-Rou Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jing-Long Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Pei-Zhi Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ai-Quan Jia
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Qian-Feng Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Pei-Zhi Zhang or Qian-Feng Zhang.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shi, YH., Jiang, YR., Liu, JL. et al. Synthesis and Structure of a Host-Guest Inclusion System Between C-iso-butyl-calix[4]methyl-resorcinarene and 1-propyl-pyrrolidine-2-carboxylic acid. J Chem Crystallogr 52, 271–275 (2022). https://doi.org/10.1007/s10870-022-00924-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-022-00924-6

Keywords

Search

Navigation