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Original Articles

Molecular tectonics

, , &
Pages 171-178 | Received 28 Aug 1994, Published online: 23 Sep 2006

References

  • Laboratoire de Diffraction des Rayons-X, Département de Chimie, Université de Montréal.
  • Killam Research Fellow, 1992–1994.
  • Wang , X. , Simard , M. and Wuest , J. D. 1994 . J. Am. Chem. Soc. , 116 : 12119 b) Wuest, J. D. In Mesomolecules: From Molecules to Materials; Mendenhall, G. D.; Greenberg, A.; Liebman, J. F., Eds.; Chapman & Hall: New York, 1995. c) Persico, F.; Wuest, J. D. J. Org. Chem. 1993, 58, 95. d) Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696. e) Gallant, M.; Phan Viet, M. T.; Wuest, J. D. J. Org. Chem. 1991, 56, 2284. f) Ducharme, Y.; Wuest, J. D. J. Org. Chem. 1988, 53, 5787.
  • Hanessian , S. , Gomtsyan , A. , Simard , M. and Roelens , S. 1994 . J. Am. Chem. Soc. , 116 : 4495 For example, the following recent references describe molecules designed to participate in complex networks of hydrogen bonds:, Zerkowski, J. A.; Mathias, J. P.; Whitesides, G. M., J. Am. Chem. Soc., 116, 4305 (1994). Zerkowski, J. A.; Whitesides, G. M., J. Am. Chem. Soc., 116, 4298 (1994). Russell, V. A.; Etter, M. C.; Ward, M. D., J. Am. Chem. Soc., 116, 1941 (1994). Kotera, M.; Lehn, J.-M.; Vigneron, J.-P., J. Chem. Soc., Chem. Commun., 1994, 197. Ung, A. T.; Bishop, R.; Craig, D. C.; Dance, I. G.; Scudder, M. L., J. Chem. Soc., Chem. Commun., 1993, 322. Copp, S. B.; Subramanian, S.; Zaworotko, M. J., Angew. Chem., Int. Ed. Engl., 32, 706 (1993). Geib, S. J.; Vicent, C.; Fan, E.; Hamilton, A. D., Angew. Chem., Int. Ed. Engl., 32, 119 (1993). Chang, Y.-L.; West, M.-A.; Fowler, F. W.; Lauher, J. W., J. Am. Chem. Soc., 115, 5991 (1993). Aakeröy, C. B.; Seddon, K. R., Chem. Soc. Rev., 1993, 397.
  • Beak , P. , Covington , J. B. , Smith , S. G. , White , J. M. and Zeigler , J. M. 1980 . J. Org. Chem. , 45 : 1354 Hammes, G. G.; Park, A. C., J. Am. Chem. Soc., 91, 956 (1969).
  • Endo , S. , Chino , T. , Tsuboi , S. and Koto , K. 1989 . Nature , 340 : 452
  • Ermer , O. 1988 . J. Am. Chem. Soc. , 110 : 3747
  • The estimated pore sizes correspond to distances between van der Waals surfaces of opposing walls defined by a projection along the channel axis.
  • For comparison, pore sizes in zeolites normally range from approximately 4 to 13 Å, and void volumes are typically less than 50%.10 The cylindrical channels in urea clathrates are nearly 5 Å in diameter, and the void volumes are approximately 30%.11
  • Davis , M. E. and Lobo , R. F. 1992 . Chem. Mater. , 4 : 756 For references, see:
  • Takemoto , K. and Sonoda , N. 1984 . Inclusion Compounds , Edited by: Atwood , J. L. , Davies , J. E. D. and MacNicol , D. D. Vol. 2 , 47 London : Academic Press . Smith, A. E. Acta Crystallogr. 1952, 5, 224.
  • Volumes occupied by guests were estimated by using the stoichiometry of the clathrate, its calculated density, and the density of the pure guest at 25°C.
  • Wang , X. , Simard , M. and Wuest , J. D. unpublished results.
  • Csákvári , E. , Shishkov , I. F. , Rozsondai , B. and Hargittai , I. 1990 . J. Mol. Struct. , 239 : 291
  • The interpenetrating networks in the expanded diamondoid lattice of clathrate 10 · 2 CH3CH2CH2CH2COOH are slightly offset along the channel axis, so the pores are somewhat smaller than those in clathrate 8 · 2 CH3CH2CH2COOH.
  • Smith , J. V. 1988 . Chem. Rev. , 88 : 149 b) For a general discussion of three-dimensional four-connected networks, see: Wells, A. F. Structural Inorganic Chemistry; Clarendon Press: Oxford, 1984; p 63.
  • Horner , J. H. and Newcomb , M. 1991 . Organometallics , 10 : 1732
  • Periodic enlargements in the channels provide additional space for the enclathration of valeric acid.

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