Skip to main content
SpringerLink
Log in

Theoretical study on the protonation of cucurbit[6]uril

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

Abstract

The most probable structures of the cucurbit[6]uril·H3O+ and cucurbit[6]uril·(H3O+)2 cationic complex species have been derived by quantum mechanical DFT calculations. In these two complexes, each of the H3O+ ions is bound by three strong linear hydrogen bonds to three carbonyl oxygen atoms of the parent macrocycle.

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

Scheme 1
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Lagona J, Mukhopadhyay P, Chakrabarti S, Isaacs L (2005) Angew Chem Int Ed 44:4844

    Article  CAS  Google Scholar 

  2. Lee JW, Samal S, Selvapalam N, Kim HJ, Kim K (2003) Acc Chem Res 36:621

    Article  CAS  Google Scholar 

  3. Liu S, Ruspic C, Mukhopadhyay P, Chakrabarti S, Zavalij PY, Isaacs L (2005) J Am Chem Soc 127:15959

    Article  CAS  Google Scholar 

  4. Freeman WA, Mock WL, Shih NY (1981) J Am Chem Soc 103:7367

    Article  CAS  Google Scholar 

  5. Mock WL, Shih NY (1983) J Org Chem 48:3618

    Article  CAS  Google Scholar 

  6. Mock WL, Shih NY (1986) J Org Chem 51:4440

    Article  CAS  Google Scholar 

  7. Mock WL, Shih NY (1988) J Am Chem Soc 110:4706

    Article  CAS  Google Scholar 

  8. Mock WL, Shih NY (1989) J Am Chem Soc 111:2697

    Article  CAS  Google Scholar 

  9. Isobe H, Tomita N, Lee JW, Kim HJ, Kim K, Nakamura E (2000) Angew Chem Int Ed 39:4257

    Article  CAS  Google Scholar 

  10. Isobe H, Sota S, Lee JW, Kim HJ, Kim K, Nakamura E (2005) Chem Commun 1549

  11. Tan Y, Choi S, Lee JW, Ko YH, Kim K (2002) Macromolecules 35:7161

    Article  CAS  Google Scholar 

  12. Márquez C, Hudgins RR, Nau WM (2004) J Am Chem Soc 126:5806

    Article  Google Scholar 

  13. Buschmann HJ, Mutihac L, Mutihac RC, Schollmeyer E (2005) Thermochim Acta 430:79

    Article  CAS  Google Scholar 

  14. Buschmann HJ, Schollmeyer E, Mutihac L (2003) Thermochim Acta 399:203

    Article  CAS  Google Scholar 

  15. Makrlík E, Vaňura P (2006) Monatsh Chem 137:157

    Article  Google Scholar 

  16. Makrlík E, Vaňura P (2006) Monatsh Chem 137:1185

    Article  Google Scholar 

  17. Dybal J, Makrlík E, Vaňura P (2007) Monatsh Chem 138:541

    Article  CAS  Google Scholar 

  18. Kříž J, Dybal J, Makrlík E, Budka J, Vaňura P (2007) Monatsh Chem 138:735

    Article  Google Scholar 

  19. Dybal J, Makrlík E, Vaňura P, Selucký P (2007) Monatsh Chem 138:1239

    Article  CAS  Google Scholar 

  20. Dybal J, Makrlík E, Vaňura P, Budka J (2008) Monatsh Chem 139:1175

    Article  CAS  Google Scholar 

  21. Dybal J, Makrlík E, Budka J, Vaňura P (2008) Monatsh Chem 139:1353

    Article  CAS  Google Scholar 

  22. Makrlík E, Dybal J, Vaňura P (2009) Monatsh Chem 140:29

    Article  Google Scholar 

  23. Makrlík E, Dybal J, Budka J, Vaňura P (2009) Monatsh Chem 140:1155

    Article  Google Scholar 

  24. Kříž J, Dybal J, Makrlík E, Budka J, Vaňura P (2010) Monatsh Chem 141:19

    Article  Google Scholar 

  25. Makrlík E, Čajan M, Budka J, Vaňura P (2011) Monatsh Chem 142:5

    Article  Google Scholar 

  26. Makrlík E, Vaňura P, Budka J (2009) Monatsh Chem 140:583

    Article  Google Scholar 

  27. Toman P, Makrlík E, Vaňura P, Kašička V, Rathore R (2010) Monatsh Chem 141:737

    Article  CAS  Google Scholar 

  28. Neugebauer R, Knoche W (1998) J Chem Soc Perkin Trans 2:529

    Google Scholar 

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

    Article  Google Scholar 

  30. Kříž J, Dybal J, Makrlík E, Vaňura P, Lang J (2007) Supramol Chem 19:419

    Article  Google Scholar 

  31. Kříž J, Dybal J, Makrlík E, Vaňura P (2008) Supramol Chem 20:387

    Article  Google Scholar 

  32. Kříž J, Dybal J, Makrlík E, Budka J, Vaňura P (2008) Supramol Chem 20:487

    Article  Google Scholar 

  33. Kříž J, Dybal J, Makrlík E, Budka J (2008) J Phys Chem A 112:10236

    Article  Google Scholar 

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

    Article  Google Scholar 

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

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  37. Becke AD (1993) J Chem Phys 98:5648

    Article  CAS  Google Scholar 

  38. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery Jr JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03, Revision C. 02, Gaussian, Wallingford, CT, USA

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”, by the Czech Ministry of Education, Youth, and Sports (project MSM 6046137307), and by the Czech Science Foundation (project P205/10/2280). Computer time at the MetaCentrum (project LM 2010005) and at the Institute of Physics (computer Luna/Apollo), Academy of Sciences of the Czech Republic, is gratefully acknowledged.

Author information

Authors and Affiliations

  1. Institute of Macromolecular Chemistry, Academy of Sciences of the Czech Republic, Prague, Czech Republic

    Petr Toman

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

    Emanuel Makrlík

  3. Department of Analytical Chemistry, Faculty of Chemical Engineering, Institute of Chemical Technology, Prague, Czech Republic

    Petr Vaňura

Authors
  1. Petr Toman
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Emanuel Makrlík
    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

Corresponding author

Correspondence to Emanuel Makrlík.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Toman, P., Makrlík, E. & Vaňura, P. Theoretical study on the protonation of cucurbit[6]uril. Monatsh Chem 142, 993–996 (2011). https://doi.org/10.1007/s00706-011-0556-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-011-0556-9

Keywords

Search

Navigation