Skip to main content
Log in

Synthesis of macrocyclic polyethers and polyether diesters and preparation of their cationic complexes

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

Abstract

New macrocyclic polyethers, 2,3,5,6-bis-[5′(5′)-chlorobenzo]-1,7,10-trioxacyclododeca-2,5-diene (I), 2,3,5,6-bis-[5′(5′)-chlorobenzo]-1,7,10,13-tetra oxacyclo pentadeca-2,5-diene (II), and 2,3,5,6-bis-[5′(5′)-chlorobenzo]-1,7,10,13,16-penta oxa cyclo octadeca-2,5-dien (III), and macrocylic lactones 2,3,5,6-bis-[5′(5′)-chlorobenzo]-1,7,10,13-tetraoxacyclopentadeca-2,5-diene-8,15-dione (IV) and 2,3,5,6-bis[5′(5′)-chlorobenzo]-1,7,10,13,16-pentaoxacyclooctadeca-2,5-diene-8,18-dione (V) were synthesized. Complexes of ligands III and V with metal cations were prepared. Furthermore, their metal-picrate extraction with some metal salts was attempted. Structures of the ligands and complexes were confirmed using spectroscopic techniques.

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

  • Arisa, J., Rojrit, R., & Mongkol, S. (2007). Stilbene-bridged 1,3-alternate calix[4]arene crown ether for selective alkali ion extraction. Tetrahedron Letters, 48, 1817–1821. DOI: 10.1016/j.tetlet.2007.01.026.

    Article  CAS  Google Scholar 

  • Bilgin, A., Ertem, B., Ağın, D. F., Gök, Y., & Karslıoğlu, S. (2006). Synthesis, characterization and extraction studies of a new vic-dioxime and its complexes containing bis(diazacrown ether) moieties. Polyhedron, 25, 3165–3172. DOI: 10.1016/j.poly.2006.05.023

    Article  CAS  Google Scholar 

  • Bradshaw, J. S., Maas, G. E., Izatt, R. M., & Christensen, J. J. (1979). Synthetic macrocyclic di-and tetraester compounds. Chemical Reviews, 79, 37–58. DOI: 10.1021/cr60317a004.

    Article  CAS  Google Scholar 

  • Bradshaw, J. S., Baxter, S. L., & Lamb, J. D. (1981). Cation-complexing properties of synthetic macrocyclic polyetherdiester ligands containing the furan, benzene, tetrahydrofuran, and thiophene subcyclic units. Journal of the American Chemical Society, 103, 1821–1827. DOI: 10.1021/ja00397a041.

    Article  CAS  Google Scholar 

  • Çakır, Ü., Özer, M., İçen, M. A., Uğraş, H. A., & Bulut, M. (2004). Synthesis of some 3-phenyl chromenone-crown ethers and equilibrium studies on complexation with ion-pair extraction of sodium and potassium dyes. Dyes and Pigments, 60, 177–185. DOI: 10.1016/j.dyepig.2003.07.005.

    Article  CAS  Google Scholar 

  • Frensdorff, H. K. (1971). Stability constants of cyclic polyether complexes with univalent cations. Journal of the American Chemical Society, 93, 600–606. DOI: 10.1021/ja00732a007.

    Article  CAS  Google Scholar 

  • Gokel, G. W., Timko, M. J., & Cram, D. J. (1975). Chiral recognition in amino-ester complexation by a cyclic polyether host compound. Journal of the Chemical Society, Chemical Communications, 1975, 394–396. DOI: 10.1039/C39750000394.

    Article  Google Scholar 

  • Huang, Z. B., Kang, T. J, & Chang, S. H. (2005). The synthesis of unique structures of tetra-crown ethers through Michael addition. Tetrahedron Letters, 46, 3461–3464. DOI: 10.1016/j.tetlet.2005.03.120.

    Article  CAS  Google Scholar 

  • Jia, X., Zhu, W., Zhang, Y., & Yan, X. (2002). Synthesis and crystal structure of complex copper nitrate with N,N′-bis(3-hydroxy-6-methyl-2-pyridylmethyl)-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane. Journal of Molecular Structure, 604, 159–164. DOI: 10.1016/S0022-2860(01)00651-2.

    Article  CAS  Google Scholar 

  • Kilic, Z., & Gunduz, N. (1986). The synthesis of asymmetric macrocyclic polyethers containing nitro group on aromatic ring. Tetrahedron, 42, 137–141. DOI: 10.1016/S0040-4020(01)87410-X.

    Article  CAS  Google Scholar 

  • Kudo, Y., Usami, J., Katsuta, S., & Takeda, Y. (2003). Solvent extraction of permanganates (Na, K) by 18-crown-6 ether from water into 1,2-dichloroethane: elucidation of an extraction equilibrium based on component equilibria. Talanta, 59, 1213–1218. DOI: 10.1016/S0039-9140(03)00029-8.

    Article  CAS  Google Scholar 

  • Knipe, A. C. (1976). Crown ethers. A new aid to synthesis and to elucidation of reaction mechanisms. Journal of Chemical Education, 53, 618–622.

    Article  CAS  Google Scholar 

  • Lamb, J. D., Izatt, R. M., Swain, C. S., Bradshaw, J. S., & Christensen, J. J. (1980). Cation complexes of crown ether diesters. Stabilities, selectivities, enthalpies, and entropies of reaction at 25.degree.C in methanol. Journal of the American Chemical Society, 102, 479–482. DOI: 10.1021/ja00522a006.

    Article  CAS  Google Scholar 

  • Lee, M., Oh, S. Y., Pathak, T. S., Paeng, I. R., Cho, B. Y., & Paeng, K. J. (2007). Selective solid-phase extraction of catecholamines by the chemically modified polymeric adsorbents with crown ether. Journal of Chromatography A, 1160, 340–344. DOI: 10.1016/j.chroma.2007.06.033.

    Article  CAS  Google Scholar 

  • Liu, Y., Zhang, Y., Bai, X., Wada, T., & Inoue, Y. (1999). Molecular design of crown ethers. 21.1,2 Synthesis of novel double-armed benzo-15-crown-5 lariats and their complexation thermodynamics with light lanthanoid nitrates in acetonitrile. Journal of Organic Chemistry, 65, 7105–7109. DOI: 10.1021/jo000815q.

    Google Scholar 

  • Pearson R. G. (1977). Hard and soft acids and bases principle in inorganic chemistry. New York: Academic Press.

    Google Scholar 

  • Pedersen, C. J. (1967). Cyclic polyethers and their complexes with metal salts. Journal of the American Chemical Society, 89, 2495–2496. DOI: 10.1021/ja00986a052.

    Article  CAS  Google Scholar 

  • Sezgin, M., Beduk, A. D., Ertul, S., & Kocak, A. (1993). The synthesis of 3 new macrocyclic ligands and preparation of some of their cationic complexes. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 23, 269–284. DOI: 10.1080/15533179308016636.

    Article  CAS  Google Scholar 

  • Smid, J., Shah, S., Wong, L., & Hurley, J. (1975). Solute binding and catalytic effects in aqueous solutions of poly(vinyl crown ethers). Journal of the American Chemical Society, 97, 5932–5933. DOI: 10.1021/ja00853a058.

    Article  CAS  Google Scholar 

  • Weber, E. (1989). Crown ethers and analogs. Chichester: Wiley.

    Google Scholar 

  • Yilmaz, M., & Deligoz, H. (1996). Selective extraction of Fe3 cation by calixarene-based cyclic ligands. Separation Science and Technology, 31, 2395–2402. DOI: 10.1080/0149639960800 1055.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Şeref Ertul.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ertul, Ş., Bedük, A.D., Bayrakci, M. et al. Synthesis of macrocyclic polyethers and polyether diesters and preparation of their cationic complexes. Chem. Pap. 62, 589–595 (2008). https://doi.org/10.2478/s11696-008-0065-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.2478/s11696-008-0065-4

Keywords

Navigation