Abstract
A new facile method of synthesis of calix[4]arene amide via the aminolysis of the calix[4]arene esters was reported. One ethyl ester of the compound (2) was aminolysized byn-butylamine. The crystal structure of compound (1)shows that one ethyl ester of compound (1) enters into thecavity of another compound (1) forming a long chainhost-guest supramolecule. From the 2D NMR data, the compound(1) does not assemble in THF or CHCl3 solution. The CH-π interaction and crystallization energy might be theimportant driving forces for forming the self-assembledcalix[4]arene.
Similar content being viewed by others
References
J. M. Lehn: Angew. Chem. 29, 1304 (1990); G. M. Whitesides, J. P. Mathias, and C. T. Seto: Science 254, 1312 (1991); D. Philp and J. F. Stoddart: Angew. Chem., Int. Ed. Engl. 35, 1154 (1996).
M. Nishio and M. Hirota: Tetrahedron 45, 7201 (1989); K. Kobayashi, Y. Asakawa, Y. Kikuchi, H. Toi, and Y. Aoyama: J. Am. Chem. Soc. 115, 2648 (1993); A. Ikeda and S. Shinkai: J. Am. Chem. Soc. 116, 3102 (1994); K. N. Koh, K. Araki, A. Ikeda, H. Otsuka, and S. Shinkai: J. Am. Chem.Soc. 118, 755 (1996); Y. Kikuchi and Y. Aoyama: Bull. Chem. Soc. Jpn. 69, 69 (1996).
J.-D. van Loon, R. G. Jansen, W. Verboom, and D. N. Reinhoudt: Tetrahedron Lett. 33, 5125 (1992); K. Koh, K. Araki, and S. Shinkai: Tetrahedron Lett. 35, 8255 (1994); J. Scheerder, R. H. Vreekamp, J. F. J. Engbersen,W. Verboom, J. P.M. van Duynhoven, and D. N. Reinhoudt: J. Org. Chem. 61, 3476 (1996); R. H. Vreekamp,W. Verboom, and D. N. Reinhoudt: Angew. Chem., Int. Ed. Engl. 35, 1215 (1996): O. Mogck, V. Bohmer, andW. Vogt: Tetrahedron 52, 8489 (1996); B. C. Hamann, K. Shimizu, and J. Rebek Jr.: Angew. Chem., Int. Ed. Engl. 35, 1326 (1996): R. K. Castellano, D. M. Rudkevich, and J. Rebek Jr.: J. Am. Chem. Soc. 118, 10002 (1996); O.Mogck, M. Pons, V. Bohmer, and W. Vogt: J. Am. Chem. Soc. 119, 5706 (1997); L. R. MacGillivray and J. L. Atwood: J. Am. Chem. 119, 6931 (1997).
S. K. Chang and I. J. Cho: J. Chem. Soc., Perkin Trans. I, 211 (1986); A. Arduini, A. Pichini, S. Reverbreri, R. Ungaro, G. D. Ardreetti, and F. Ugozobi: Tetrahedron 42, 2089 (1986).
Y.Wu, H.-B. Liu, J. Hu, Y.-J. Liu, C.-Y. Duan, and Z. Xu: Chemistry in China (in press); Y. Wu, X.-P. Shen, C.-Y. Duan, Y.-J. Liu, and Z. Xu: Tetrahedron Lett. (in press).
M. Cabrera, E. A. Castro, M. Salas, J. G. Santos, and P. Sepulveda: J. Org. Chem. 56, 5324 (1991); E. A. Castro, F. Ibanez, M. Salas, and J. G. Santos: J. Org. Chem. 56, 4819 (1991); P. Haberfield and J. J. Cincotta: J. Org. Chem. 55, 1334 (1990).
F. J. Steemers, W. Verboom, D. N. Reinhoudt, E. B. van der Tol, and J. W. Verhoeven: J. Am. Chem. Soc. 117, 9408 (1995); P. Lhotak and S. Shinkai: Tetrahedron Lett. 36, 4829 (1995); S. J. Meunier and R. Roy: Tetrahedron Lett. 37, 5469 (1996).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Wu, Y., Liu, HB., Liu, YJ. et al. A Facile Method of Synthesis of a Calix[4]arene Amide and the Crystal Structure of a Self-assembled Calix[4]arene Amide via van Der Waals Interaction. Journal of Inclusion Phenomena 36, 473–478 (2000). https://doi.org/10.1023/A:1008161320091
Issue Date:
DOI: https://doi.org/10.1023/A:1008161320091