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Calixarenes 50th Anniversary: Commemorative Issue pp 371–387Cite as

Thermodynamic and Electrochemical Aspects of p-tert-Butylcalix[n]arenes (n = 4, 6, 8) and Their Interactions with Amines

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Abstract

Attention is drawn to the need of detailed thermodynamics in calixarene chemistry. The reasons for increasing efforts in this area are underlined and suggestions for new issues to be addressed are given. The solution thermodynamics of p-tert-butylcalix[n]arenes (n = 4, 6, 8) is discussed with particular reference to transfer Gibbs energies which reflect the selective solvation that the tetramer and the octamer undergo in the various solvents. This is followed by recent solution studies on amine-p-tert-butylcalix[n]arene (n=4,6,8) in nitrobenzene and in benzonitrile at 298.15 K which indicate the lower acidic character of the tetramer relative to the hexamer and the octamer in these solvents. As an implication of these results, very low conductivities are observed in studies involving the interaction of the former with amines. Thus, thermodynamic studies suggest that p-tert-butylcalix[4]arene interacts with triethylamine in benzonitrile and in nitrobenzene through hydrogen bonding or ion-pair formation. A thermodynamic cycle is used to investigate the effect associated with the interaction of the amine with the tetramer in these solvents.

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References

  1. C. J. Pedersen: J. Incl. Phenom. 6, 341 (1988).

    Article  Google Scholar 

  2. J. M. Lehn: J. Incl Phenom. 6, 351 (1988).

    Article  CAS  Google Scholar 

  3. A. F. Danil de Namor and L. Ghousseini: J. Chem. Soc., Faraday Trans. 1 80, 2349 (1984).

    Article  CAS  Google Scholar 

  4. A. F. Danil de Namor and L. Ghousseini: J. Chem. Soc., Faraday Trans. 1 81, 781 (1985).

    Article  CAS  Google Scholar 

  5. A. F. Danil de Namor and L. Ghousseini: J. Chem. Soc., Faraday Trans. 1 82, 3275 (1986).

    Article  CAS  Google Scholar 

  6. A. F. Danil de Namor: J. Chem. Soc., Faraday Trans. 1 84, 2441 (1988).

    Article  CAS  Google Scholar 

  7. A. F. Danil de Namor: PureAppl. Chem. 61, 2121 (1990).

    Article  Google Scholar 

  8. A. Zinke and E. Ziegler: Ber. 77B, 264 (1944).

    CAS  Google Scholar 

  9. C. D. Gutsche and R. Muthukrishnan: J. Org. Chem. 43, 4905 (1978).

    Article  CAS  Google Scholar 

  10. A. F. Danil de Namor: Pure Appl. Chem. 65, 193 (1993).

    Article  CAS  Google Scholar 

  11. R. Ungaro and A. Pochini: p. 127 in Calixarenes: A Versatile Class of Macrocyclic Compounds, J. Vicens and V. Böhmer (Eds.), Kluwer Academic Publishers, Dordrecht (1990).

    Google Scholar 

  12. M.J. Schwing-Weill and M. A. McKervey: p. 149 in Calixarenes: A Versatile Class of Macrocyclic Compounds, J. Vicens and V. Böhmer (Eds.), Kluwer Academic Publishers, Dordrecht (1990).

    Google Scholar 

  13. G. Barrett, M. A. McKervey, J. F. Malone, A. Walker, F. Arnaud-Neu, L. Guerra, M. J. Schwing-Weill, C. D. Gutsche, and D. R. Stewart: J. Chem. Soc., Perkin Trans. 2 1475 (1993) and references therein.

    Google Scholar 

  14. A. F. Danil de Namor, N. Apaza de Sueros, M. A. McKervey, G. Barrett, F. Arnaud-Neu, and M. J. Schwing-Weill: J. Chem. Soc., Chem. Commun. 1546 (1991).

    Google Scholar 

  15. A. F. Danil de Namor, M. T. Garrido Pardo, L. Muñoz, D. A. Pacheco Tanaka, F. J. Sueros Velarde, and M. C. Cabaleiro: J. Chem. Soc., Chem. Commun. 855 (1992).

    Google Scholar 

  16. A. F. Danil de Namor, P. M. Blackett, M. T. Garrido Pardo, D. A. Pacheco Tanaka, F. J. Sueros Velarde, and M. C. Cabaleiro: Pure Appl. Chem. 65, 415 (1993).

    Article  CAS  Google Scholar 

  17. A. F. Danil de Namor, M. T. Garrido Pardo, D. A. Pacheco Tanaka, F. J. Sueros Velarde, J. D. Cárdenas García, M. C. Cabaleiro, and J. M. A. Al Rawi: J. Chem. Soc., Faraday Trans. (special issue in Biophysical Chemistry) 89, 2727 (1993).

    Article  CAS  Google Scholar 

  18. A. F. Danil de Namor, M. C. Cabaleiro, B. M. Vuano, M. Salomon, O. I. Pieroni, D. A. Pacheco Tanaka, C. Y. Ng, M. A. Llosa Tanco, N. M. Rodriguez, J. Cárdenas García, and A. R. Casal: PureAppl. Chem. 66, 435 (1994).

    Article  CAS  Google Scholar 

  19. A. F. Danil de Namor, F. J. Sueros Velarde, L. Pulcha Salazar, (work in progress) (1993).

    Google Scholar 

  20. A. F. Danil de Namor, M. A. Llosa Tanco, M. Salomon, and C. Y. Ng: J. Phys. Chem. 98, 11796 (1994).

    Article  CAS  Google Scholar 

  21. Commission V.8, IUPAC: Critical Evaluation on Thermodynamic Aspects of Macrocyclic Chemistry (1993), work in progress.

    Google Scholar 

  22. J. Suurkuusk and I. Wadsö: Chem. Scr. 20, 155 (1982).

    CAS  Google Scholar 

  23. A. F. Danil de Namor: unpublished results.

    Google Scholar 

  24. D. Hallen and I. Wadsö: Pure Appl. Chem. 61, 123 (1989).

    Article  CAS  Google Scholar 

  25. L. J. Bauer and C. D. Gutsche: J. Am. Chem. Soc. 107, 6063 (1985).

    Article  CAS  Google Scholar 

  26. A. F. Danil de Namor, F. J. Sueros Velarde and I. Gómez Orellana (unpublished work).

    Google Scholar 

  27. R. C. Weast (Ed.): Handbook of Chemistry and Physics, 62nd edn., CRC Press (1981).

    Google Scholar 

  28. A. F. Danil de Namor, R. Traboulssi, and M. Salomon: J. Chem. Soc., Faraday Trans. 186, 2193 (1990).

    Article  Google Scholar 

  29. M. Bastos, S. Hägg, P. Lönnbro, and I. Wadsö: J. Biochem. Biophys. Methods 23, 255 (1991).

    Article  CAS  Google Scholar 

  30. S. L. Randzio and J. Suurkuusk: in Biological Microcalorimetry, A. E. Beezer (Ed.), Academic Press, London (1980).

    Google Scholar 

  31. L. E. Briggner and I. Wadsö: J. Biochem. Biophys. Methods 22, 101 (1991).

    Article  CAS  Google Scholar 

  32. A. F. Danil de Namor, R. Traboulssi, and D. F. V. Lewis: J. Am. Chem. Soc. 112, 8442 (1990).

    Article  CAS  Google Scholar 

  33. R. Fernandez Prini: in Physical Chemistry of Organic Solvents, A. K. Covington and T. Dickinson (Eds.), Plenum Press (1973).

    Google Scholar 

  34. P. Walden: Z. Phys. Chem. 55, 207 (1906).

    CAS  Google Scholar 

  35. P. Walden: Z. Phys. Chem. 78, 257 (1912).

    CAS  Google Scholar 

  36. A. F. Danil de Namor and J. Wang: in progress (1993).

    Google Scholar 

  37. N. S. Isaacs: Physical Organic Chemistry, Longman (1987).

    Google Scholar 

  38. P. Gans, A. Sabatini, and A. Vacca: Inorg. Chim. Acta 18, 237 (1976).

    Article  CAS  Google Scholar 

  39. P. H. Bevington: Data Reduction and Error Analysis in the Physical Sciences, McGraw-Hill, New York (1969).

    Google Scholar 

  40. W. H. Lawton and E. A. Sylvestre: Thermometries 13, 461 (1971).

    Google Scholar 

  41. C. Bavoux and M. Perrin: J. Incl. Phenom. 14, 247 (1992).

    Article  CAS  Google Scholar 

  42. C. D. Gutsche, M. Iqbal, and I. Alam: J. Am. Chem. Soc. 109, 4314 (1987).

    Article  CAS  Google Scholar 

  43. V. Böhmer and J. Vicens: in Calixarenes: A Versatile Class of Macrocyclic Compounds, J. Vicens and V. Böhmer (Eds.), Kluwer Academic Publishers, Dordrecht (1990).

    Google Scholar 

  44. G. Görmar, K. Seiffarth, M. Schulz, and C. L. Chachimbombo: J. Prakt. Chem. 333, 475 (1991).

    Article  Google Scholar 

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Authors and Affiliations

  1. Laboratory of Thermochemistry, Department of Chemistry, University of Surrey, Guildford, Surrey, GU2 5XH, UK

    A. F. Danil de Namor, J. Wang, I. Gomez Orellana, F. J. Sueros Velarde & D. A. Pacheco Tanaka

Authors
  1. A. F. Danil de Namor
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  2. J. Wang
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  3. I. Gomez Orellana
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  4. F. J. Sueros Velarde
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  5. D. A. Pacheco Tanaka
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Editor information

Editors and Affiliations

  1. Ecole Européenne des Hautes, Etudes des Industries Chimiques de Strasbourg (EHICS), France

    J. Vicens  & Z. Asfari  & 

  2. The University of Western Australia, Perth, Australia

    J. M. Harrowfield

Additional information

This paper is dedicated to the commemorative issue on the 50th anniversary of calixarenes.

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© 1994 Springer Science+Business Media Dordrecht

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Danil de Namor, A.F., Wang, J., Orellana, I.G., Sueros Velarde, F.J., Pacheco Tanaka, D.A. (1994). Thermodynamic and Electrochemical Aspects of p-tert-Butylcalix[n]arenes (n = 4, 6, 8) and Their Interactions with Amines. In: Vicens, J., Asfari, Z., Harrowfield, J.M. (eds) Calixarenes 50th Anniversary: Commemorative Issue. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-0267-4_24

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  • DOI: https://doi.org/10.1007/978-94-011-0267-4_24

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-4118-8

  • Online ISBN: 978-94-011-0267-4

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