Ir al menú de navegación principal Ir al contenido principal Ir al pie de página del sitio
ACI Avances en Ciencias e Ingenierías

SECCIÓN A: CIENCIAS EXACTAS

Vol. 2 Núm. 2 (2010)

Síntesis de 2,8,14,20-tetra-n-butilpirogalol[4]areno y estudio computacional conformacional

DOI
https://doi.org/10.18272/aci.v2i2.22
Enviado
julio 2, 2015
Publicado
2010-06-01

Resumen

Este trabajo presenta la obtención de aluminosilicatos mesoporosos generados mediante condensación de xerogel a partir de alcóxido de silicio (TEOS) y precursores de aluminio de diversas fuentes. Se usaron nitrato de aluminio (NAN), como fuente inorgánica y el alcoxido, tris-sec-butilato de aluminio (TBA) como fuente órgano-metálica. Se analizó la importancia del tamaño de cadena de alquilo en el surfactante (Tritón-X) en el proceso de condensación de la red, y su posterior influencia sobre el área superficial y en la obtención de mesoporos en los materiales. Adicionalmente se estudió la influencia de las variables mencionadas sobre la estabilidad hidrotermal de los aluminosilicatos.

viewed = 782 times

Citas

  1. Liam, C., Palmer, and Jr., J. R. 2005. "Hydrocarbon binding inside ahexameric pyrogallol[4]arene capsule." Org. Lett. 7(5), 787-789.
  2. Shivanyuk, A., Friese, J., Döring, S., and Jr, J. R. 2003. "Solvent-stabilized molecular capsules." J. Org. Chem. 68(17), 6489-6496.
  3. Shivanyuk, A., Far, A. R., and Jr., J. R. 2002. "Rigid tetranitroresorcinarenes." Org. Lett. 4(9), 1555-1558.
  4. Gutsche, D., Zouhair, A., Böhmer, V, Harrowfield, J., Vicens, J.,andeds,M. S.2001. "Synthesis of calixarenes and thiacalixarenes." Springer Netherlands. 1-25, 155­181.
  5. Niederl, J.,Niederl, V, and Grumer, J. 1940. "Steric hin­drance in ketone-phenol condensations. the condensa­tion of guaiacol with cyclic ketones." J. Am. Chem. Soc. 62, 320-322.
  6. Lewis, P. and Strongin, R. 1998. "Resorcinarenes with deepened polyaromatic lower cavities: Synthesis and structure." J. Org. Chem. 63(17), 6065-6067.
  7. Moore, D. and Matthews, S. 2009. "O-alkyl resorcare- nes: where are we now?." Journal of Inclusion Pheno­mena andMacrocyclic Chemistry. 65(1-2), 137-155.
  8. Botta, B., Monache, G. D., Rosa, C. D., Seri, C., Be­nedetti, E., Iacovino, R., Botta, M., Corelli, F., Masig- nani, V, Tafi, A., Gacs-Baitz, E., Santini, A., and Misi­ti, D. 1997. "Synthesis of c-alkylcalix[4]arenes. 5. De­sign, synthesis, computational studies, and homodime­rization of polymethylene-bridged resorc[4]arenes." J. Org. Chem. 62(6), 1788-1794.
  9. Botta, B., Monache, G. D., Ricciardi, P., Zappia, G., Se­ri, C., Gacs-Baitz, E., Csokasi, P., and Misiti, D. 2000. "Synthesis of c-alkylcalix[4]arenes, 6 The interaction of resorcin[4]arenes with Felll in chloroform." European Journal ofOrganic Chemistry. 5, 841-847.
  10. Botta, B., D"™Acquarica, I., Nevola, L., Sacco, F., Lo­pez, S. V, Zappia, G., Fraschetti, C., Speranza, M., Ta­fi, A., Caporuscio, F., Letzel, M., and Mattay, J. 2007. "Bis(diamido)-bridged basket resorcin[4]arenes as enan- tioselective receptors for amino acids and amines." Eu­ropean Journal of Organic Chemistry. 36, 5995-6002.
  11. Vicens, J., Böhmer, V, and (eds.) Kluwer Academic Pu­blishers, D. 1990. "Calixarenes: a versatile class of ma­crocyclic compounds." The Netherlands. 5-27.
  12. Gutsche, D. 1990. "Calixarenes revisited monographs in supramolecular chemistry." The Royal Society of Che­mistry, Thomas Graham House. 1-7,10-28,41-78.
  13. Gopalsamuthiram, V and Wulff, W. 2004. "A new con­vergent strategy for the synthesis of calixarenes via a triple annulation of fischer carbene complexes." J. Am. Chem. Soc. 126(43), 13936-13937.
  14. Sakhaii, P., Verdier, L., Ikegami, T., and Griesinger, C. 2002 "Synthesis of a novel class of carbohydrate- containing calix[4]resorcinarene adopting an asymme­trical diamond structure." Helvetica Chimica Acta. 85(11), 3895-3908.
  15. Atkinson, M., Buar, D., Sokolov, A., Frii, T., Robinson, C., Bilal, M., Sinada, N., Chevannes, A., and MacGilli- vray, L. 2008. "General application of mechanochemis- try to templated solid-state reactivity: rapid and solvent­free access to crystalline supermolecules." Chem. Com­mun. 48,5713-5715.
  16. Barrett, E., Dale, T., and Rebek, J. 2007. "Synthesis and assembly of monofunctionalized pyrogallolarene capsu­les monitored by fluorescence resonance energy trans­fer." Chem. Commun. 41,4224-4226.
  17. Antesberger, J., Cave, G., Ferrarelli, A., Heaven, M., Raston, C., and Atwood, J. 2005. "Solvent-free, di­rect synthesis of supramolecular nano-capsules ." Chem. Commun. 7, 892-894.
  18. Kleij, A., Souto, B., Pastor, C., Prados, P., and Mendo­za, J. D. 2004. "Multinuclear calixarene synthons with covalently linked aryl-palladium(ii) complexes." J. Org. Chem. 69(19), 6394-6403.
  19. Yang, Y. and Swager, T. 2006. "Main-chain calixarene polymers: Conformational effects on polymerization." Macromolecules 39(6), 2013-2015.
  20. Abourahma, H., Bodwell, G., J.Lu, Moulton, B., Pottie, I., Walsh, R., and Zaworotko, M. 2003. "Coordination polymers from calixarene-like [Cu2(dicarboxylate)2]4 building blocks: Structural diversity via atropisome- rism." Crystal Growth & Design 3(4), 513-519.
  21. Ueda, J., Kamigaito, M., and Sawamoto, M. 1998. "Calixarene-core multifunctional initiators for the ruthenium-mediated living radical polymerization of methacrylates." Macromolecules. 31(20), 6762-6768.
  22. Atwood, J. and Barbour, L. 2003. "Molecular graphics: From science to art." Crystal Growth and Design 3, 3-8.
  23. Avram, L. and Cohen, Y. 2004. "Self-recognition, struc­ture, stability, and guest affinity of pyrogallol[4]arene and resorcin[4]arene capsules in solution." J. Am. Chem. Soc. 126(37), 11556-11563.
  24. Houmadi, S., Coquière, D., Legrand, L., Fauré, M., Goldmann, M., Reinaud, O., and Rémita, S. 2007. "Architecture-controlled "˜smart"™ calix[6]arene self-assemblies in aqueous solution". Langmuir 23(9), 4849-4855.
  25. Notestein, J., Katz, A., and Iglesia, E. 2006. "Energetics of small molecule and water complexation in hydropho­bic calixarene cavities." Langmuir 22(9), 4004-4014.
  26. Dalgarno, S., Power, N., Warren, J., and Atwood, J. 2008. "Rapid formation of metal-organic nano-capsules gives new insight into the self-assembly process ". Chem. Commun. 13, 1539-1541.
  27. Dalgarno, S., Claudio-Bosque, K., Warren, J., Glass, T., and Atwood, J. 2008. "Interpenetrated nano-capsule net­works based on the alkali metal assisted assembly of p- carboxylatocalix[4]arene-o-methyl ether". Chem. Com­mun. 12, 1410-1412.
  28. Kulikov, O., Daschbach, M., Yamnitz, C., Rath, N., and Gokel, G. 2009. "Self-assembled, cogged hexameric na­notubes formed from pyrogallol[4]arenes with a unique branched side chain ". Chem. Commun. 48, 7497-7499.
  29. Ha, J., Solovyov, A., and Katz, A. 2009. "Synt­hesis and characterization of accessible metal surfa­ces in calixarene-bound gold nanoparticles". Langmuir 25(18), 10548-10553.
  30. Lynam, C., Jennings, K., Nolan, K., Kane, P, McKer- vey, A., and Diamond, D. 2002. "Tuning and enhancing enantioselective quenching of calixarene hosts by chiral guest amines." Anal. Chem. 74(1), 59-66.
  31. Buccella, D., Tanski, J., and Parkin, G. 2007. "Factors Influencing Coordination versus Oxidative Addition of C-H Bonds to Molybdenum and Tungsten: Structural and Spectroscopic Evidence That the Calixarene Frame­work Promotes C-H Bond Activation." Organometallics. 26(14), 3275-3278.
  32. Liu, L., Zakharov, L., Golen, J., Rheingold, A., and Hanna, T. 2008. "Synthesis and characterization of bismuth(III) and antimony(III) calixarene complexes." Inorg. Chem 47(23), 11143-11153.
  33. Grannas, M., Hoskins, B., and Robson, R. 1994. "Synt­hesis and x-ray crystal structures of a calixarene-related, tetraamino, tetraphenolic, polynucleating macrocyclic ligand and its ZnIR and CoIID derivatives." Inorg. Chem. 33(6), 1071-1079.
  34. Zorzi, R. D., Guidolin, N., Randaccio, L., Purrello, R., and Geremia, S. 2009. "Nanoporous crystals of calixare- ne/porphyrin supramolecular complex functionalized by diffusion and coordination of metal ions." J Am Chem Soc. 131(7), 2487-2489.
  35. Scott, P., Dalgarno, J., Warren, J., Teat, S., and Atwood, J. 2009. "Enhanced control over metal composition in mixed Ga/Zn and Ga/Cu coordinated pyrogallol[4]arene nanocapsules ." Chem. Commun. 23, 3348-3350.
  36. Kotch, F., Sidorov, V, Lam, Y., Kayser, K., Li, H., Kau- cher, M., and Davis, J. 2003. "Water-mediated associa­tion provides an ion pair receptor." J Am Chem Soc 125(49), 15140-15150.
  37. Blazejczyk, A., Szczupak, M., Wieczorek, W., Cmoch, P., Appetecchi, G., Scrosati, B., Kovarsky, R., Golod- nitsky, D., and Peled, E. 2005. "Anion-binding cali­xarene receptors: Synthesis, microstructure, and effect on properties of polyether electrolytes." Chem Mater 17(6), 1535-1547.
  38. Israeli, Y. and Detellier, C. 1997. "Complexation of the sodium cation by a calix[4]arene tetraester in solution. formation of a 2:1 calixarene: sodium complex." J. Phys. Chem. B 101(10), 1897-1901.
  39. Jin, T. and Ichikawa, K. 1991. "Dissociation kinetics of calixarene ester-sodium(1+) complexes: effect of the so­dium ion exchange reaction on sodium-23 longitudinal magnetization recovery curves and proton NMR spec­tra." J.Phys. Chem. 95(6), 2601-2606.
  40. Jin, P., Dalgarno, S., Barnes, C., Teat, S., and Atwood, J. 2008. "Ion transport to the interior of metal-organic pyrogallol[4]arene nanocapsules." J Am Chem Soc 130(51), 17262-17263.
  41. Sarri, P., Venturi, F., Cuda, F., and Roelens, S. 2004. "Binding of acetylcholine and tetramethylammonium to flexible cyclophane receptors: Improving on binding ability by optimizing host"™s geometry." J. Org. Chem. 69(11), 3654-3661.
  42. Bassil, D., Dalgarno, S., Cave, G., Atwood, J., and Tuc­ker, S. 2007. "Spectroscopic investigations of adma en­capsulated in pyrogallol[4]arene nanocapsules." J Phys Chem.B 111(30), 9088-9092.
  43. Dalgarno, S., Szabo, T., Siavosh-Haghighi, A., Deaky- ne, C., Adams, J., and Atwood, J. 2009. "Exploring the limits of encapsulation within hexameric pyroga- llol[4]arene nano-capsules ." Chem. Commun. 11,1339­1341.
  44. Witte, T., Decker, B., Mattay, J., and Huber, C. 2004. "Formation of branched calixarene aggregates a time- resolved static light scattering study." J. Am. Chem. Soc. 126(30), 9276-9282.
  45. Cave, G., Dalgarno, S., Antesberger, J., Ferrarelli, M., McKinlay, R., and Atwood, J. enero 2008. "Investiga­tions into chain length control over solid-state pyro- gallol[4]arene nanocapsule packing ." Supramolecular Chemistry. 20(1,2), 157-159.
  46. Lonetti, B., Nostro, P. L., Ninham, B., and Baglioni, P. 2005. "Anion effects on calixarene monolayers: A Hof­meister series study." Langmuir. 21(6), 2242-2249.
  47. Dalgarno, S., Power, N., Antesberger, J., McKinlay, R., and Atwood, J. 2006. "Synthesis and structural charac­terisation of lower rim halogenated pyrogallol[4]arenes: bi-layers and hexameric nano-capsules ." Chem. Com­mun. 36, 3803-3805.
  48. Zambrano, C., Kass, J., Dueno, E., Ke, Y., and H. 2006. "Crystal structure of 2,8,14,20- tetranaphthylpyrogallol[4]arene." Journal of Chemical Crystallography. 36(1), 67-70.
  49. Dueno, E., Ray, T., Salvatore, R., Zambrano, C., Ze­ller, M., and Hunter, A. 2007. "2,8,14,20-tetrakis(4- hydroxyphenyl)pyrogallol[4]arene dimethylformamide hexasolvate." Acta Cryst. E63, O3533-O3534.
  50. Kass, J., Zambrano, C., Zeller, M., Hun­ter, A., and Dueno, E. 2006. "2,8,14,20-tetraphenylpyrogallol[4]arene dimethylformamide octasolvate." Acta Cryst. E62, O3179-O3180.
  51. Dueno, E., Hunter, A., Zeller, M., Ray, T., Salvatore, R., and Zambrano, C. 2008. "Crystal structure of 2, 8, 14, 20-tert -butylpyrogallol[4]arene." Journal of Chemical Crystallography. 38(3), 181-187.
  52. Sheldrick 2003. "G. M. sadabs in saint-plus (version 6.45)." Bruker Axs Inc., Madison, Wisconsin, USA. 2003.
  53. Sheldrick 2000. "G. M. shelxtl (version 6.14) program for crystal structure refinement", Bruker Axs Inc., Ma­dison, Wisconsin, USA. 2003.
  54. 2000. "Cache for windows (version 5.0)." Fujitsu Ame­rica, Inc.
  55. Stewart, J. 1990. "MOPAC: A general molecular orbital package." Quant. Chem. Prog. Exch. 10, 86-98 .
  56. Alemán, C., Luque, F., and Orozco, M. 1993. "Suita­bility of the PM3-derived molecular electrostatic poten­tials." J. Comp. Chem. 14, 799-808.
  57. Stewart, J. 2004. "Optimization of parameters for semi­empirical methods IV: Extension of MNDO, AM1, and PM3 to more main group elements." J. Mol. Model. 155­164.
  58. Orozco, M., Bachs, M., and Luque, F. 1995. "Develop­ment of optimized MST/SCRF methods for semiempiri­cal calculations. The MNDO and PM3 Hamiltonians." J. Comp. Chem. 16, 563-585.
  59. Rzepa, H. S., Yi, M. Y, Karelson, M. M., and Zerner, M. C. 1991. "Geometry optimization at the semiempiri­cal self-consistent-reaction-field level using the AMPAC and MOPAC programs.." J. Chem. Soc. 5, 635-637.
  60. L.Farrugia 1997. "ORTEP-3 for windows cryst."
  61. Weisstein, E. "Pyramidal Frustum." From mathworld-a wolfram web resource. http://mathworld.wolfram.com/pyramidalfrustum.html.
  62. Cave, G. and Ferrarelli, M. 2005. "Nano-dimensions for the pyrogallol[4]arene cavity." Chem. Commun. 22, 2787-2789.
  63. Maerz, A., Haunani, T., Power, N., Deakyne, C., and At­wood, J. 2010. "Dimeric nanocapsule induces conforma­tional change." Chem. Commun. 46, 1235-1237.