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Monatshefte für Chemie - Chemical Monthly

, Volume 139, Issue 11, pp 1353–1355 | Cite as

DFT-calculated structure of protonated tetraphenyl p-tert-butylcalix[4]arene tetraketone

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

Abstract

Using DFT calculations, two of the most probable structures (A, B) of the tetraphenyl p-tert-butylcalix[4]arene tetraketone·H3O+ cationic complex species were derived. The hydroxonium ion H3O+, placed in the coordination cavity formed by the calix[4]arene lower-rim groups, is bound by strong hydrogen bonds to the phenoxy oxygen atoms of the calix[4]arene ligand (structures A, B) and also to one carbonyl oxygen (structure B).

Keywords

Calixarenes; Macrocycles; Protonation; DFT; Structure. 

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References

  1. Böhmer, V 1995Angew Chem34713CrossRefGoogle Scholar
  2. Gutsche, CD 1998Calixarenes RevisitedThe Royal Society of ChemistryCambridgeGoogle Scholar
  3. Arduini, A, Pochini, A, Reverberi, S, Ungaro, R 1986Tetrahedron422089CrossRefGoogle Scholar
  4. Arduini, A, Ghidini, E, Pochini, A, Ungaro, R, Andreetti, GD, Calestani, G, Ugozzoli, F 1988J Inclusion Phenom6119CrossRefGoogle Scholar
  5. Arnaud-Neu, F, Collins, EM, Deasy, M, Ferguson, G, Harris, SJ, Kaitner, B, Lough, AJ, McKervey, MA, Marques, E, Ruhl, BL, Schwing-Weill, MJ, Seward, EM 1989J Am Chem Soc1118681CrossRefGoogle Scholar
  6. Arnaud-Neu, F, Barrett, G, Harris, SJ, Owens, M, McKervey, MA, Schwing-Weill, MJ, Schwinté, P 1993Inorg Chem322644CrossRefGoogle Scholar
  7. Ohto, K, Murakami, E, Shinohara, T, Shiratsuchi, K, Inoue, K, Iwasaki, M 1997Anal Chim Acta341275CrossRefGoogle Scholar
  8. Ye, Z, He, W, Shi, X, Zhu, L 2001J Coord Chem54105CrossRefGoogle Scholar
  9. Danil de Namor, AF, Chahine, S, Kowalska, D, Castellano, EE, Piro, OE 2002J Am Chem Soc12412824CrossRefGoogle Scholar
  10. Marcos, PM, Ascenso, JR, Segurado, MAP, Pereira, JLC 2002J Inclusion Phenom42281CrossRefGoogle Scholar
  11. Marcos, PM, Félix, S, Ascenso, JR, Segurado, MAP, Pereira, JLC, Khazaeli-Parsa, P, Hubscher-Bruder, V, Arnaud-Neu, F 2004New J Chem28748CrossRefGoogle Scholar
  12. Makrlík, E, Vaňura, P 2006Monatsh Chem1371185CrossRefGoogle Scholar
  13. Dybal, J, Makrlík, E, Vaňura, P 2007Monatsh Chem138541CrossRefGoogle Scholar
  14. Kříž, J, Dybal, J, Makrlík, E, Budka, J, Vaňura, P 2007Monatsh Chem138735CrossRefGoogle Scholar
  15. Dybal, J, Makrlík, E, Vaňura, P, Selucký, P 2007Monatsh Chem1381239CrossRefGoogle Scholar
  16. Dybal J, Makrlík E, Vaňura P, Budka J (2008) Monatsh Chem 139: (in press)Google Scholar
  17. Makrlík, E, Vaňura, P 1985Talanta32423CrossRefGoogle Scholar
  18. Makrlík E, Budka J, Vaňura P, Dybal J (2008) Monatsh Chem 139: (in press)Google Scholar
  19. 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 (2004) Gaussian 03, Revision C. 02, Gaussian Inc., Wallingford, CTGoogle Scholar
  20. Kříž, J, Dybal, J, Makrlík, E 2006Biopolymers82536CrossRefGoogle Scholar
  21. Kříž, J, Dybal, J, Makrlík, E, Vaňura, P, Lang, J 2007Supramol Chem19419CrossRefGoogle Scholar
  22. Kříž, J, Dybal, J, Makrlík, E, Vaňura, P 2008Supramol Chem20387CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2008

Authors and Affiliations

  • Jiří Dybal
    • 1
  • Emanuel Makrlík
    • 2
    Email author
  • Jan Budka
    • 3
  • Petr Vaňura
    • 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

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