Abstract
The structures ethanol solvated complexes of para-sulphonato-calix[4]arene with magnesium and calcium have been determined. Both show the classical bilayer structure of para-sulphonato-calix[4]arene. The cations are situated between the bilayers. In the case of the magnesium complex the cation is octahedrally coordinated by six water molecules, however for the calcium complex the cation is coordinated in two different geometries by water molecules, bridging oxygen atoms of the sulphonate anions and an oxygen of an ethanol molecule. Both complexes contain an ethanol molecule embedded in the macrocyclic cavity.
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Steed, J.W., Atwood, J.L.: Supramolecular Chemistry, 2nd edn. Wiley, UK (2009)
Gutsche, C.D.: Calixarenes Revisited: Monographs in Supramolecular Chemistry. The Royal Society of Chemistry, Cambridge (1998)
Perret, F., Coleman, A.W.: Biochemistry of anionic calix[n]arenes. Chem. Commun. 47, 7303–7319 (2011)
Hardie, M.J.: Hydrogen bonded network structures constructed from molecular hosts. Struct. Bond. 111, 139–174 (2004)
Shinkai, S., Mori, S., Tsubaki, T., Sone, T., Manabe, O.: New water soluble host molecules derived from calix[6]arene. Tetrahedron Lett. 25(46), 5315–5318 (1984)
Coleman, A.W., Bott, S.G., Morley, S.D., Means, C.M., Robinson, K.D., Zhang, H.M., Atwood, J.L.: Novel layer structure of sodium calix[4]arenesulfonate complexes: a class of organic clay mimics. Angew. Chem. Int. Ed. 27, 1361–1362 (1988)
Orr, G.W., Barbour, L.J., Atwood, J.L.: Controlling molecular self-organization: formation of nanometer-scale spheres and tubules. Science 285(5430), 1049–1052 (1999)
Perret, F., Lazar, A.N., Coleman, A.W.: Biochemistry of the para-sulphonato-calix[n]arenes. Chem. Commun. 23, 2425–2438 (2006)
Coleman, A.W., Jebors, S., Cecillon, S., Perret, P., Garin, D., Marti-Battle, D., Moulin, M.: Toxicity and biodistribution of para-sulphonato-calix[4]arene in mice. New J. Chem. 32, 780–782 (2008)
Memmi, L., Lazar, A., Brioude, A., Ball, V., Coleman, A. W.: Protein–calixarene interactions: complexation of bovine serum albumin by sulfonatocalix[n]arenes. Chem. Commun. 2474–2475 (2001)
Lazar, A., Da Silva, E., Navaza, A., Barbey, C., Coleman, A.W.: A new packing motif for para-sulfonatocalix[4]arene: the solid state structure of the para-sulfonatocalix[4]arene d-arginine complex. Chem. Commun. 19, 2162–2163 (2004)
Danylyuk, O., Suwinska, K.: Solid-state interactions of calixarenes with biorelevant molecules. Chem. Commun. 39, 5799–5813 (2009)
Da Silva, E., Lazar, A.N., Coleman, A.W.: Biopharmaceutical applications of calixarenes. J. drug deliv. sci. technol. 14, 3–20 (2004)
Perret, F., Tauran, Y., Suwinska, K., Kim, B.J., Chassain-Nely, C., Boulet, M., Coleman, A.W.: Molecular recognition and transport of active pharmaceutical ingredients on anionic calix[4]arene capped silver nanoparticles. J. Chem. (2013). doi:10.1155/2013/191828
Da Silva, E., Ficheux, D., Coleman, A.W.: Anti-thrombotic activity of water-soluble calix[n] arenes. J. Inclusion Phenom. Macrocycl. Chem. 17(52), 201–206 (2005)
Tsou, L.K., Dutschman, G.E., Gullen, E.A., Telpoukhovskaia, M., Cheng, Y.C., Hamilton, A.D.: Discovery of a synthetic dual inhibitor of HIV and HCV infection based on a tetrabutoxy-calix[4]arene scaffold. Bioorg. Med. Chem. Lett. 20(7), 2137–2139 (2010)
Atwood, J. L., Bridges, R. J., Juneja, R. K., Singh. A. K.: US Patent 5 489 612, 1996
Bott, S.G., Coleman, A.W., Atwood, J.L.: Intercalation of cationic, anionic, and molecular species by organic hosts. preparation and crystal structure of [NH4]6[calix[4]arenesulfonate][MeOSO3]·(H2O). J. Am. Chem. Soc. 110(2), 610–611 (1988)
Atwood, J.L., Coleman, A.W., Zhang, H., Bott, S.G.: Organic clays. Synthesis and structure of Na5[calix[4] arene sulfonate]·12H2O, K5[calix[4]arene sulfonate]·8H2O, Rb5[calix[4]arene sulfonate]·5H2O, and Cs5[calix[4] arene sulfonate]·4H2O. J. Inc. Phenom. 7, 203–211 (1989)
Fucke, K., Anderson, K.M., Filby, M.H., Henry, M., Wright, J., Mason, S.A., Gutmann, M.J., Barbour, L.J., Oliver, C.L., Coleman, A.W., Atwood, J.L., Howard, J.A.K., Steed, J.W.: The structure of water in p-sulfonatocalix[4]arene. Chem. Eur. J. 17, 10259–10271 (2011)
Da Silva, E., Nouar, F., Nierlich, M., Rather, B., Zaworotko, M.J., Barbey, C., Navaza, A., Coleman, A.W.: A comparative structural study of four para-sulphonato-calix-[4]-arene organic di- and triammonium cation complexes. Cryst. Eng. 6, 123–135 (2003)
Atwood, J.L., Barbour, L.J., Hardieb, M.J., Raston, C.L.: Metal sulfonatocalix[4,5]arene complexes: bi-layers, capsules, spheres, tubular arrays and beyond. Coord. Chem. Rev. 222, 3–32 (2001)
Nichols, P.J., Makha, M., Raston, C.L.: Confinement of nucleic acid bases and related compounds using tetra-para-sulfonatocalix[4] arene. Cryst. Growth Des. 6, 1161–1167 (2006)
Atwood, J.L., Barbour, L.J., Dalgarno, S., Raston, C.L., Webb, H.R.: Supramolecular assemblies of p-sulfonatocalix[4]arene with aquated trivalent lanthanide ions. J. Chem. Soc. Dalton Trans. 23, 4351–4356 (2002)
Lesniewska, B., Danylyuk, O., Suwinska, K., Wojciechowski, T., Coleman, A.W.: Supramolecular versatility in the solid-state complexes of para-sulphonatocalix[4]arene with phenanthroline. Cryst. Eng. Commun. 13, 3265–3272 (2011)
Greenwood, N.N., Earnshaw, A.: Chemistry of the Elements, 1st edn. Pergamon Press, Oxford (1984)
Yang, W.H., Lee, W., Hellinga, H., Yang, J.J.: Structural analysis, identification, and design of calcium-binding sites in proteins. Proteins Struct. Funct. Genet. 47, 344–356 (2002)
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Y.T. thanks the Unversité Lyon 1 for financial support.
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Suwinska, K., Janneau, E., Tauran, Y. et al. The solid-state structures of the ethanol solvated complexes of para-sulphonato-calix[4]arene with magnesium and calcium ions. J Incl Phenom Macrocycl Chem 79, 177–183 (2014). https://doi.org/10.1007/s10847-013-0342-x
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DOI: https://doi.org/10.1007/s10847-013-0342-x