Abstract
The ligand 5,11,17,23-tetra-t-butyl-25,27-di(phenylmethoxy)-26,28-di(2-methoxy-ethoxy)calix[4]arene,designed as an analogue of some calixcrown speciesin order to evaluate possible origins of their selectivity in alkali metal ion binding, has been synthesised and structurally characterised by X-ray crystallography. The crystals are monoclinic, P21/n, a = 15.940(6), b = 19.388(5), c = 20.020(5) Å,β = 109.10(2) deg., Z = 4, conventional R on |F| being 0.073 for 3454 independent, ’observed‘ (I > 3σ(I)) reflections. 1H-NMR studies in 1:1 CD3CN/CDCl3solvent have shown that the ligand exerts a strong preference for the lighteralkali metal ions (Li+ and Na+) contrary to the binding behaviour of knowncalixcrowns. This may reflect interactions restricted to the lower rim donor atoms without concomitant interaction with the calixarene π-electrons, perhaps because the latter interactions are substituted by those with the benzyl group π-electrons.
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References
C.D. Gutsche: Calixarenes, Monographs in Supramolecular Chemistry, Vol 1. J.F. Stoddart (Ed.), The Royal Society of Chemistry, Cambridge (1989).
D.M. Roundhill: Progr. Inorg. Chem. 43, 553 (1995).
V. Böhmer: Angew. Chem., Int. Ed. Engl. 34, 713 (1995).
A. Casnati, A. Pochini, R. Ungaro, F. Ugozzoli, F. Arnaud, S. Fanni, M-J. Schwing, R.J.M. Egberink, F. de Jong and D.N. Reinhoudt: J. Am. Chem. Soc. 117, 2767 (1995) and references therein.
Z. Asfari, S. Wenger, and J. Vicens: in J. Vicens, Z. Asfari and J.M. Harrowfield (Eds.): Calixarenes’ 50th Anniversary, Kluwer Academic Publishers, Dordrecht, 1995, p. 137 (also published as J. Incl. Phenom. 19, 137 (1994)) and references therein.
S. Wenger, Z. Asfari and J. Vicens: Pure Appl. Chem. 67, 1037 (1995).
R. Abidi, Z. Asfari, J.M. Harrowfield, A.N. Sobolev and J. Vicens: Aust. J. Chem. 49, 183 (1996), and references therein.
R. Abidi, Z. Asfari, J.M. Harrowfield, C. Nauman, A.N. Sobolev and J. Vicens: Anales Quim. (Int. Ed.) 92, 51 (1996).
R. Ungaro, A. Arduini, A. Casnati, O. Ori, A. Pochini, and F. Ugozzoli: in G. Wipff (Ed.), Computational Approaches in Supramolecular Chemistry, NATO ASI Series, Mathematical and Physical Sciences, No. 426, Kluwer Academic Publishers, Dordrecht, p. 277 (1996).
J.W. Caldwell and P.A. Kollman: J. Am. Chem. Soc. 117, 4177 (1995).
M. Nishio, Y. Umezawa, M. Hirota and T. Takeuchi: Tetrahedron 51, 8665 (1995).
W. Xu, R.J. Puddephatt, K.W. Muir and A.A. Torabi: Organometallics 13, 3054 (1994).
G.D. Andreetti and F. Ugozzoli in J. Vicens and V. Böhmer (Eds.): Calixarenes: A Versatile Class of Macrocyclic Compounds, Kluwer Academic Publishers, Dordrecht, Holland, p. 87 (1991).
J. Blixt and C. Detellier: J. Am. Chem. Soc. 117, 8536 (1995).
J.M. Harrowfield, M. Mocerino, B.W. Skelton, C.R. Whitaker and A.H. White: Aust. J. Chem. 47, 1185 (1994).
E.M. Collins, M.A. McKervey, and S.J. Harris: J. Chem. Soc., Perkin Trans. 1372 (1989).
E.M. Collins, M.A. McKervey, E. Madigan, M.B. Moran, M. wens, G. Ferguson, and S.J. Harris: J. Chem. Soc., Perkin Trans. 13137 (1991).
S.R. Hall, H.D. Flack and J.M. Stewart: The XTAL 3.2 Reference Manual, Universities of Western Australia, Geneva and Maryland, (1992).
A. Arduini, A. Pochini, S. Reverberi and R. Ungaro: J. Chem. Soc., Chem. Commun.981 (1984).
F. Ohseto, T. Sakaki, K. Araki, S. Shinkaji: Tetrahedron Lett. 34, 2149 (1993).
T. Jin, K. Ichikawa: J. Phys. Chem. 95, 2601 (1991).
F. Arnaud-Neu, E.M. Collins, M. Deasy, G. Ferguson, S.J. Harris, B. Kaitner, S.J. Lough, M.A. McKervey, E. Marques, B. Ruhl, M-J. Schwing-Weill and E.M. Seward: J. Am. Chem. Soc. 111, 8681 (1989).
K. Ohto, E. Murakami, K. Shiratsuchi, K. Inoue and M. Iwasaki: Chem. Lett.173 (1996).
A. Ikeda, H. Tsuzuki and S. Shinkai: J. Chem. Soc., Perkin Trans 22073 (1994).
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ABIDI, R., HARROWFIELD, J.M., SKELTON, B.W. et al. Synthesis, Structure and Alkali Metal Ion Binding Properties of a Podand Polyether Derived from Calix[4]arene, 5,11,17,23-tetra-tert-butyl-25,27-di(phenylmethoxy)-26,28-di(2‘-methoxyethoxy)-calix[4]arene. Journal of Inclusion Phenomena 27, 291–302 (1997). https://doi.org/10.1023/A:1007981710765
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DOI: https://doi.org/10.1023/A:1007981710765