Skip to main content
Log in

Structural characterization of a complex derived from lead(II) perchlorate and acridono-18-crown-6 ether

  • Original Research
  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

This paper describes the X-ray crystal structure of a complex of acridono-18-crown-6 ether 3 and lead(II) perchlorate. The structure shows a π–π bonded heterodimer in the crystal. One part of the dimer moves to 9-hydroxyacridine tautomeric form upon lead(II) complexation, in which the lead(II) ion is eight-coordinated and fits well into the cavity of the macrocycle. The other part of the dimer stays in the 9(10H)-acridone tautomeric form, which favors water complexation. The average bond distance of the two tricyclic units (3.5 Å) indicates a strong π–π interaction. The X-ray studies also revealed a cation–π interaction between lead(II) and the electron-rich acridone moiety.

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.

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Ovchinnikov YA (1979) Physico-chemical basis of ion transport through biological membranes: ionophores and ion channels. Eur J Biochem 94:321–336

    Article  CAS  Google Scholar 

  2. Hunter CA, Sanders JKM (1990) The nature of π–π interactions. J Am Chem Soc 112:5525–5534

    Article  CAS  Google Scholar 

  3. Anslyn EV, Dougherty DA (2005) In: Murdzek J (ed) Modern physical organic chemistry. University Science Books, Sausalito

    Google Scholar 

  4. Pecsi I, Leveles I, Harmat V, Vertessy BG, Toth J (2010) Aromatic stacking between nucleobase and enzyme promotes phosphate ester hydrolysis in dUTPase. Nucleic Acids Res 38:7179–7186

    Article  CAS  Google Scholar 

  5. Mahadevi AS, Sastry GN (2013) Cation−π interaction: its role and relevance in chemistry, biology, and material Science. Chem Rev 113:2100–2138

    Article  CAS  Google Scholar 

  6. Nagy GN, Marton L, Contet A, Ozohanics O, Ardelean LM, Révész A, Vékey K, Irimie FD, Vial H, Cerdan R, Vértessy BG (2014) Composite aromatic boxes for enzymatic transformations of quaternary ammonium substrates. Angew Chem Int Ed Engl 53:13471–13476

    Article  CAS  Google Scholar 

  7. Desvergne JP, Czarnik AW (eds) (1997) Chemosensors of ion and molecule recognition NATO ASI Series C. Kluwer, Dordrecht 492

    Google Scholar 

  8. Grant LD (2009) In: Lippmann M (ed) Lead and compounds. Environmental toxicants: human exposures and their health effects, 3rd edn. Wiley, Hoboken. Wiley-Interscience

  9. Needleman H (2004) Lead poisoning. Annu Rev Med 55:209–222

    Article  CAS  Google Scholar 

  10. Dapul H, Laraque D (2014) Lead poisoning in children. Adv Pediatr 61:313–333

    Article  Google Scholar 

  11. Bazzicalupi C, Bencini A, Fusi V, Giorgi C, Paoletti P, Valtancoli B (1999) Lead complexation by novel phenanthroline-containing macrocycles. J Chem Soc Dalton 3:393–400

    Article  Google Scholar 

  12. Aguilar JC, de San Miguel ER, de Gyves J, Bartsch RA, Kim M (2001) Design, synthesis and evaluation of diazadibenzocrown ethers as Pb2+ extractants and carriers in plasticized cellulose triacetate membranes. Talanta 54:1195–1204

    Article  CAS  Google Scholar 

  13. Esteban D, Avecilla F, Platas-Iglesias C, Mahía J, de Blas A, Rodríguez-Blas T (2002) Lead(II) complexes with macrocyclic receptors derived from 4,13-diaza-18-crown-6. Inorg Chem 41:4337–4347

    Article  CAS  Google Scholar 

  14. Esteban D, Avecilla F, Platas-Iglesias C, de Blas A, Rodríguez-Blas T (2003) Synthesis and structural characterisation of lead(II) isothiocyanate complexes with receptors derived from 1,10-diaza-15-crown-5. Polyhedron 22:2709–2717

    Article  CAS  Google Scholar 

  15. Grzegorzewski P, Nikonowicz A, Jurczak J (2004) Complexation of Pb2+ by macrocyclic benzo- and pyridinophanes. J Incl Phenom 49:97–100

    Article  CAS  Google Scholar 

  16. Lee SH, Kim JY, Kim SK, Lee JH, Kim JS (2004) Pyrene-appended calix[4] crowned logic gates involving normal and reverse PET: NOR, XNOR and INHIBIT. Tetrahedron 60:5171–5176

    Article  CAS  Google Scholar 

  17. Buschmann HJ, Schollmeyer E (2010) Stability constants and thermodynamic data for the complexation of Pb2+ by noncyclic, macrocyclic and macrobicyclic ligands in aqueous solution. J Coord Chem 55:287–291

    Article  Google Scholar 

  18. Farina P, Latter T, Levason W, Reid G (2013) Lead(II) tetrafluoroborate and hexafluorophosphate complexes with crown ethers, mixed O/S- and O/Se-donor macrocycles and unusual [BF4] and [PF6] coordination. Dalton T 42:4714–4724

    Article  CAS  Google Scholar 

  19. Szalay L, Farkas V, Vass E, Hollósi M, Móczár I, Pintér Á, Huszthy P (2004) Synthesis and selective lead(II) binding of achiral and enantiomerically pure chiral acridono-18-crown-6 ether type ligands. Tetrahedron Asymmetry 15:1487–1493

    Article  CAS  Google Scholar 

  20. Németh T, Kormos A, Tóth T, Balogh G, Huszthy P (2015) Synthesis and cation binding of acridono-18-crown-6 ether type ligands. Monatsh Chem 146:1291–1297

    Article  Google Scholar 

  21. Huszthy P, Köntös Z, Vermes B, Pintér Á (2001) Synthesis of novel fluorescent acridono- and thioacridono-18-crown-6 ligands. Tetrahedron 57:4967–4975

    Article  CAS  Google Scholar 

  22. CrysAlisPRO (2011) Oxford diffraction. Agilent Technologies UK Ltd, Yarnton

    Google Scholar 

  23. Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JAK, Puschmann H (2009) OLEX2: a complete structure solution, refinement and analysis program. J Appl Cryst 42:339–341

    Article  CAS  Google Scholar 

  24. Sheldrick GM (1997) SHELX97, programs for crystal structure analysis. University of Gottingen, Gottingen

    Google Scholar 

  25. Huszthy P, Vermes B, Báthori N, Czugler M (2003) Synthesis and X-ray crystallographic studies of novel proton-ionizable nitro- and halogen-substituted acridono-18-crown-6 chromo- and fluorogenic ionophores. Tetrahedron 59:9371–9377

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Financial supports of the Hungarian Scientific Research Fund (OTKA K112289, K109486 and NK84008), the CRP/HUN14-01 ICGEB Research Grant and the New Széchenyi Development Plan (TÁMOP-4.2.1/B-09/1/KMR-2010-0002) are gratefully acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Péter Huszthy.

Additional information

Dedicated to Professor Magdolna Hargittai on the occasion of her 70th birthday.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Németh, T., Golcs, Á., Leveles, I. et al. Structural characterization of a complex derived from lead(II) perchlorate and acridono-18-crown-6 ether. Struct Chem 26, 1467–1471 (2015). https://doi.org/10.1007/s11224-015-0657-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-015-0657-x

Keywords

Navigation