Skip to main content
SpringerLink
Log in

Experimental and theoretical study on complexation of the cesium cation with calix[4]arene-(1,2-phenylene-crown-6,crown-6)

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Extraction experiments in the two-phase water–nitrobenzene system and γ-activity measurements were used to determine the stability constant of the calix[4]arene-(1,2-phenylene-crown-6,crown-6)–Cs+ complex dissolved in nitrobenzene saturated with water. Further, applying quantum-mechanical density functional theory (DFT) calculations, the most probable structures A and B of this cationic complex species, which are obviously in a dynamic equilibrium, were derived.

Graphical Abstract

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

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Böhmer V (1995) Angew Chem Int Ed 34:713

    Article  Google Scholar 

  2. Alfieri C, Dradi E, Pochini A, Ungaro R, Andreetti GD (1983) J Chem Soc Chem Commun 1075

  3. Asfari Z, Wenger S, Vicens J (1994) J Incl Phenom 19:137

    Article  CAS  Google Scholar 

  4. Kim JS, Vicens J (2009) J Incl Phenom Macrocycl Chem 63:189

    Article  CAS  Google Scholar 

  5. Gutsche CD (1998) Calixarenes revisited. The Royal Society of Chemistry, Cambridge

    Google Scholar 

  6. Ungaro R, Casnati A, Ugozzoli F, Pochini A, Dozol JF, Hill C, Rouquette H (1994) Angew Chem Int Ed 33:1506

    Article  Google Scholar 

  7. Casnati A, Pochini A, Ungaro R, Ugozzoli F, Arnaud F, Fanni S, Schwing MJ, Egberink RJM, de Jong F, Reinhoudt DN (1995) J Am Chem Soc 117:2767

    Article  CAS  Google Scholar 

  8. Thuéry P, Nierlich M, Bryan JC, Lamare V, Dozol JF, Asfari Z, Vicens J (1997) J Chem Soc Dalton Trans 4191

  9. Deng Y, Sachleben RA, Moyer BA (1995) J Chem Soc Faraday Trans 91:4215

    Article  CAS  Google Scholar 

  10. Sachleben RA, Bonnesen PV, Descazeaud T, Haverlock TJ, Urvoas A, Moyer BA (1999) Solvent Extr Ion Exch 17:1445

    Article  CAS  Google Scholar 

  11. Haverlock TJ, Bonnesen PV, Sachleben RA, Moyer BA (2000) J Incl Phenom Macrocycl Chem 36:21

    Article  CAS  Google Scholar 

  12. Wintergerst MP, Levitskaia TG, Moyer BA, Sessler JL, Delmau LH (2008) J Am Chem Soc 130:4129

    Article  CAS  Google Scholar 

  13. Rais J (1971) Collect Czech Chem Commun 36:3253

    Article  CAS  Google Scholar 

  14. Makrlík E, Vaňura P (1985) Talanta 32:423

    Article  Google Scholar 

  15. Makrlík E, Božek F (1998) Polish J Chem 72:949

    Google Scholar 

  16. Makrlík E, Hálová J, Kyrš M (1984) Collect Czech Chem Commun 49:39

    Article  Google Scholar 

  17. Makrlík E, Vaňura P (1998) ACH Models Chem 135:213

    Google Scholar 

  18. Makrlík E, Dybal J, Vaňura P (2013) J Radioanal Nucl Chem 295:1299

    Article  Google Scholar 

  19. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785

    Article  CAS  Google Scholar 

  20. Becke D (1993) J Chem Phys 98:5648

    CAS  Google Scholar 

  21. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery Jr JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox J E, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann R E, Yazyev O, Austin A J, Cammi R, Pomelli C, Ochterski J W, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, Revision C.01. Gaussian Inc., Wallingford

  22. Kříž J, Dybal J, Makrlík E (2006) Biopolymers 82:536

    Article  Google Scholar 

  23. Kříž J, Dybal J, Makrlík E, Budka J, Vaňura P (2009) J Phys Chem A 113:5896

    Google Scholar 

  24. Kříž J, Toman P, Makrlík E, Budka J, Shukla R, Rathore R (2010) J Phys Chem A 114:5327

    Google Scholar 

  25. Kříž J, Dybal J, Makrlík E, Vaňura P, Moyer BA (2011) J Phys Chem B 115:7578

    Google Scholar 

  26. Makrlík E, Toman P, Vaňura P (2012) Monatsh Chem 143:199

    Article  Google Scholar 

  27. Toman P, Makrlík E, Vaňura P (2012) Monatsh Chem 143:985

    Article  CAS  Google Scholar 

  28. Makrlík E, Toman P, Vaňura P (2013) Monatsh Chem 144:919

    Article  Google Scholar 

  29. Asfari Z, Thuéry P, Nierlich M, Vicens J (1999) Tetrahedron Lett 40:499

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Grant Agency of the Faculty of Environmental Sciences, Czech University of Life Sciences, Prague, Project No. 42900/1312/3114 “Environmental Aspects of Sustainable Development of Society,” and by the Czech Ministry of Education, Youth, and Sports (Project MSM 6046137307).

Author information

Authors and Affiliations

  1. Faculty of Environmental Sciences, Czech University of Life Sciences, Prague, Czech Republic

    Emanuel Makrlík

  2. Institute of Chemical Technology, Prague, Czech Republic

    Michal Bureš & Petr Vaňura

  3. Laboratoire de Chimie Analytique et Sciences Séparatives, Institut Pluridisciplinaire Hubert Curien, Strasbourg Cedex, France

    Zouhair Asfari

Authors
  1. Emanuel Makrlík
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Michal Bureš
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Petr Vaňura
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zouhair Asfari
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Emanuel Makrlík.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Makrlík, E., Bureš, M., Vaňura, P. et al. Experimental and theoretical study on complexation of the cesium cation with calix[4]arene-(1,2-phenylene-crown-6,crown-6). Monatsh Chem 145, 1395–1399 (2014). https://doi.org/10.1007/s00706-014-1200-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-014-1200-2

Keywords

Search

Navigation