Abstract
A novel receptor possessing two complexation sites and bearing 1,3-alternate conformation based on thiacalix[4]arene, confirmed by single crystal X-ray analysis, was prepared. The tetrathiacalix[4]arene diamide shows strong intramolecular hydrogen bonding. The binding behavior towards K+ and halides has been examined by 1H NMR titration experiments.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References and notes
(a) L. Stryer (ed.): Biochemistry, 4th edn, W. H. Freeman and Co., New York (1998); (b) G. Tumcharern, T. Tuntulani, S.J. Coles, M.B. Hursthouse, and J.D. Kilburn: Org. Lett. 5, 4971 (2003).
(a) A. Casnti, F. Sansone, and R. Ungaro: Acc. Chem. Res. 36, 246 (2003); (b) B. Moss: Chem. And Ind. 407 (1996); (c) C. Glidewell: Chem. Ber. 26, 137 (1990).
For a comprehensive review of all aspects of calixarene chemistry, see: (a) C.D. Gutsche: Calixarenes, The Royal Society of Chemistry, Cambridge, (1989); (b) J. Vicens, and V. Böhmer: CALIXARENES: A Versatile Class of Macrocyclic Compounds, Kluwer Academic Publishers, Cambridge (1990).
(a) H. Kumagi, M. Hasegawa, S. Miyanari, Y. Sugawa, Y. Sato, T. Hori, S. Ueda, H. Kamiyama, and S. Miyano: Tetrahedron Lett. 38, 3971 (1997); (b) N. Iki, C. Kabuto, T. Fukushima, H. Kumagai, H. Takeya, S. Miyanari, T. Miyashi, and S. Miyano: Tetrahedron 56, 1437 (2000).
(a) B. Dietrich: Pure Appl. Chem. 65, 1457 (1993); (b) J.L. Atwood, K.T. Holman, J.W. Steed: Chem. Comm.1401 (1996); (c) L. Rason: Aust. J. Chem. 29, 1635 (1976).
(a) S.E. Matthews, P.D. Beer: in Z. Asfari, V. Bohmer, J. Harrowfield, and J. Vicens. (eds.) Calixarenes 2001, Kluwer Academic; Dordrecht (2001); (b) F.C.J.M. van Veggel, N. Verboom, and D.N. Reinhoudt: Chem. Rev. 94, 281 (1994).
(a) N.J. Wolf, E.M. Georgiev, A.T. Yordanov, B.R. Whittlesey, H.F. Koch, and D.M. Roundhill: Polyhedron 18, 855 (1999); (b) P.D. Beer, M.G.B. Drew, D. Hesek, K.C. Nam: J. Chem. Soc. Chem. Commun. 107 (1997); (c) P.A. Gale, C. Zheng, M.G.B. Drew, J.A. Heath, and P.D. Beer. Polyhedron 17, 405 (1998).
(a) B. Schazmann, N. Alhashimy, and D. Diamond: J. Am. Chem. Soc. 128, 8607 (2006); (b) P. Zlatuskova, I. Stibor, M. Tkadlecova, and P. Lhotak: Tetrahedron 60, 11383 (2004); (c) J. Budka, P. Lhotak, V. Michlova, and I. Stibor: Tetrahedron Lett. 42, 1583 (2001); (d) N. Pelizzi, A. Casnati, A. Friggeri, and R. Ungaro: J.␣Chem. Soc. Chem. Commun. 1307 (1998).
(a) P.R.A. Webber, and P.D. Beer: J. Chem. Soc. Dalton Trans. 2249 (2003); (b) A. Arduini, E. Brindani, G. Giorgi, A. Pochini, and A. Secchi: J. Org. Chem. 67, 6188 (2002); (c) S.O. Kang, and K.C. Nam: Bull. Korean Chem. Soc. 23, 640 (2002); (d) P.D. Beer, and P.A. Gale: Angew. Chem. Indt. Ed. Engl. 40, 86 (2001).
(a) L. Salmon, P. Thuéry, E. Riviere, S. Miyamoto, T. Yamato, and M. Ephritikhine: New J. Chem. 30, 1220 (2006); (b) U. Darbost, M.-N. Rager, S. Petit, I. Jabin, and O. Reinaud: J. Am. Chem. Soc. 127, 8517 (2005); (c) P.K. Panda, and C.-H. Lee: Org. Lett. 6, 671 (2004); (d) A. Arduini, E. Brindani, G. Giorgi, A. Pochini, and A. Secchi: J. Org. Chem. 67, 6188 (2002); (e) J.B. Cooper, M.G.B. Drew, and P.D. Beer: J. Chem. Soc. Dalton Trans. 2721 (2000); (f) D.M. Rudkevich, Z. Brzozka, M. Palys, H.C. Visser, W. Verboom, and D.N. Reinhoudt: Angew. Chem. Int. Ed. Engl. 33, 467 (1994).
(a) N. Iki, F. Narumi, T. Suzuki, A. Sugawara, and M. Sotaro: Chem. Lett. 1065 (1998); (b) N. Iki, N. Morohashi, F. Narumi, T. Fujimoto, T. Suzuki, and M. Sotaro: Tetrahedron Lett. 40, 7337 (1999).
(a) A. Ikeda, S. Shinkai: J. Am. Chem. Soc. 116, 3102 (1994); (b) K.N. Koh, K. Araki, S. Shinkai, Z. Asfari, and J. Vicens: Tetrahedron Lett. 36, 6095 (1995); K. Iwamoto, and S. Shinkai: J.␣Org. Chem. 57, 7066 (1992).
(a) J. Scheerder, J.P.M. van Duynhoven, J.F.J. Engbersen, and D.N. Reinhoudt: Angew. Chem. Int. Ed. Engl. 35, 1090 (1996); (b) D.N. Rudkevich, W. Verboom and D. N. Reinhoudt: J. Org. Chem. 59, 3683 (1994).
H. A. Benesi, and J.H. Hildebrand: J. Am. Chem. Soc. 71, 2703 (1949).
Acknowledgments
We would like to thank the OTEC at Saga University for financial support and the EPSRC UK National Crystallography Service at Southampton University and Daresbury Laboratory.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Yamato, T., Pérez-Casas, C., Rahman, S. et al. Synthesis and Structure of a 1,3-alternate-Thiacalix[4]arene diamide Derivative. J Incl Phenom Macrocycl Chem 58, 193–197 (2007). https://doi.org/10.1007/s10847-006-9144-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10847-006-9144-8