Advertisement

Monatshefte für Chemie - Chemical Monthly

, Volume 139, Issue 10, pp 1175–1178 | Cite as

Protonation of 25,27-bis(1-octyloxy)calix[4]arene-crown-6 in the 1,3-alternate conformation

  • Jiří Dybal
  • Emanuel MakrlíkEmail author
  • Petr Vaňura
  • Jan Budka
Article

Abstract

From extraction experiments in the two-phase water-nitrobenzene system and γ-activity measurements, the stability constant of protonated 1,3-alternate-25,27-bis(1-octyloxy)calix[4]arene-crown-6 in nitrobenzene saturated with water was determined. By using DFT calculations, the most probable structure of the 1,3-alternate-25,27-bis(1-octyloxy)calix[4]arene-crown-6 · H3O+ complex species was derived.

Keywords

Calixarenes; Macrocycles; Protonation; DFT; Structure. 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Böhmer, V 1995Angew Chem34713CrossRefGoogle Scholar
  2. Alfieri C, Dradi E, Pochini A, Ungaro R, Andreetti GD (1983) J Chem Soc Chem Commun:1075Google Scholar
  3. Asfari, Z, Wenger, S, Vicens, J 1994J Incl Phenom Mol Recogn19137CrossRefGoogle Scholar
  4. Gutsche, CD 1998Calixarenes RevisitedThe Royal Society of ChemistryCambridgeGoogle Scholar
  5. Ungaro, R, Casnati, A, Ugozzoli, F, Pochini, A, Dozol, JF, Hill, C, Rouquette, H 1994Angew Chem331506CrossRefGoogle Scholar
  6. Casnati, A, Pochini, A, Ungaro, R, Ugozzoli, F, Arnaud, F, Fanni, S, Schwing, MJ, Egberink, RJM, de Jong, F, Reinhoudt, DN 1995J Am Chem Soc1172767CrossRefGoogle Scholar
  7. Thuery P, Nierlich M, Bryan JC, Lamare V, Dozol JF, Asfari Z, Vicens J (1997) J Chem Soc Dalton Trans:4191Google Scholar
  8. Makrlík, E, Vaňura, P 2006Monatsh Chem1371185CrossRefGoogle Scholar
  9. Dybal, J, Makrlík, E, Vaňura, P 2007Monatsh Chem138541CrossRefGoogle Scholar
  10. Kříž, J, Dybal, J, Makrlík, E, Budka, J, Vaňura, P 2007Monatsh Chem138735CrossRefGoogle Scholar
  11. Dybal, J, Makrlík, E, Vaňura, P, Selucký, P 2007Monatsh Chem1381239CrossRefGoogle Scholar
  12. Rais, J 1971Collect Czech Chem Commun363253Google Scholar
  13. Daňková, M, Makrlík, E, Vaňura, P 1997J Radioanal Nucl Chem221251CrossRefGoogle Scholar
  14. Makrlík, E, Hálová, J, Kyrš, M 1984Collect Czech Chem Commun4939Google Scholar
  15. Makrlík, E, Vaňura, P 1996J Radioanal Nucl Chem214339CrossRefGoogle Scholar
  16. Makrlík, E, Vaňura, P 2006Monatsh Chem137157CrossRefGoogle Scholar
  17. Makrlík E, Vaňura P (2008) (unpublished results)Google Scholar
  18. Frisch, MJ, Trucks, GW, Schlegel, HB, Scuseria, GE, Robb, MA, Cheeseman, JR, Montgomery, JA,Jr, 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 2004Gaussian 03, Revision C. 02Gaussian Inc.Wallingford, CTGoogle Scholar
  19. Kříž, J, Dybal, J, Makrlík, E 2006Biopolymers82536CrossRefGoogle Scholar
  20. Kříž, J, Dybal, J, Makrlík, E, Vaňura, P, Lang, J 2007Supramol Chem19419CrossRefGoogle Scholar
  21. Kříž J, Dybal J, Makrlík E, Vaňura P (2008) Supramol Chem (in press)Google Scholar
  22. Makrlík, E, Vaňura, P 1985Talanta32423CrossRefGoogle Scholar
  23. Makrlík, E 1992Collect Czech Chem Commun57289CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2008

Authors and Affiliations

  • Jiří Dybal
    • 1
  • Emanuel Makrlík
    • 2
    Email author
  • Petr Vaňura
    • 3
  • Jan Budka
    • 3
  1. 1.Institute of Macromolecular ChemistryAcademy of Sciences of the Czech RepublicPragueCzech Republic
  2. 2.Faculty of Applied Sciences, University of West BohemiaPilsenCzech Republic
  3. 3.Institute of Chemical TechnologyPragueCzech Republic

Personalised recommendations