198 Topics in Current Chemistry Editorial Board: A. de Meijere KN ...

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Functional Organic Zeolite Analogues 159 redox catalysts and have been incorporated in a variety of porous structures. As for the guests, there are good examples of hydrocarbon incorporation. The use of efficient solid catalysts may play an essential role in the construction of waste-free and workup-free molecular transformations which are friendly to the environment and resource-saving. 5.3 Organic Zeolite Analogues as Enzyme Mimics in Water From the environmental point of view, the most ideal solvent is water. This is also the medium where enzymatic reactions take place. There are a couple of questions in the use of water for the zeolite analogues. One is as for the maintenance of structures; can a hydrogen-bonded or metal-coordinated network survive in an aqueous environment? The other is with respect to the efficiency of catalysis; even when the structure is maintained, can a guest be bound to the host via either hydrogen bonding or coordination to the metal in preference to the water? Both questions arise from the very polar nature of water, which acts as a strong hydrogen-bond former as well as a potent ligand to a metal ion, especially a Lewis acid centre. The strength of the metal-coordination networks against hydrolysis may be proved by the fact that many of them are prepared by crystallisation from an aqueous medium. Use of water-tolerable Lewis acids such as lanthanoid metals may be an interesting extension. The water-tolerance of a hydrogen-bonded network is also proved. For example, host 35 (Fig. 10), when immersed in water, not only maintains its hydrogen-bonded network but actually incorporates a large number (~ 21) of water molecules in each huge cavity and still retains single-crystallinity. In a similar manner, host 29 (Fig. 9) adsorbs ~ 16 water molecules. Furthermore, this host preferentially binds highly hydrophilic guest molecules such as ethanol, ethyl acetate and acetonitrile in water via host-guest hydrogen bonding. This suggests that cavity-bound polar guests can be activated via hydrogen bonding in water in a similar manner as in enzymatic catalyses. In fact, there is a remarkable apparent relevance between microporous organic solids and enzyme proteins in the maintenance of structures and functions. Acknowledgements. The support of our research activities by CREST (Core Research for Evolutional Science and Technology) of Japan Science and Technology Corporation and also by Grant-in-Aids from the Ministry of Education, Science, and Culture of the Japanese Government is greatly acknowledged. I am also grateful to my capable co-workers, especially Dr. K. Endo (CREST, Kyushu University) and Dr. K. Kobayashi (Tsukuba University) for their collaboration. 6 References 1. Breck DW (1974) Zeolite molecular sieves, structure, chemistry, and use. Wiley, New York 2. Herron N (1991) In: Atwood JL, Davies JED, MacNicol DD (eds) Inclusion compounds, vol 5, chap 3. Academic Press, Oxford 3. Suib SL (1993) Chem Rev 93:803
160 Y. Aoyama 4. Hölderich W, Hesse M, Näumann F (1988) Angew Chem Int Ed Engl 27:226 5. Thomas JM (1988) Angew Chem Int Ed Engl 27:1673 6. Weber E (1987) Top Curr Chem 140:3 7. Zaworokto (1994) Chem Soc Rev 23:283 8. Bishop R (1996) Chem Soc Rev 25:311 9. Zimmerman SC (1977) Science 276:543 10. Schmidt GM (1971) Pure Appl Chem 27:647 11. MacNicol DD, McKendrick JJ, Wilson DR (1978) Chem Soc Rev 7:65 12. Lehn JM, Atwood JL, Davies JED, MacNicol DD, Vögtle F (eds) (1996) Comprehensive supramolecular chemistry, vol 6. Pergamon Press, Oxford 13. Atwood JL, Davies JED, MacNicol DD (eds) (1984) Inclusion compounds, vols 1–3. Academic Press, London; (1991) Inclusion compounds, vols 4, 5. Oxford University Press, Oxford 14. Baughman RH, Galvão DS (1993) Nature 735:365 15. Evans KE, Hutchinson IJ (1991) Nature 353:124 16. Kitaigorodskii AI (1973) Molecular crystals and molecules. Academic Press, New York 17. Desiraju GR (1989) Crystal engineering: the design of organic solids. Elsevier,Amsterdam 18. Pang L, Brisse F (1994) Can J Chem 72:2318 19. Toda F (1991) In: Atwood JL, Davies JED, MacNicol DD (eds) Inclusion compounds, vol 4, chap 4. Oxford University Press, Oxford 20. Byrn MP, Curtis CJ, Goldberg I, Hsiou Y, Khan SI, Sawin PA, Tendick SK, Strouse CE (1991) J Am Chem Soc 113:6549 21. Byrn MP, Curtis CJ, Goldberg I, Hsiou Y, Khan SI, Sawin PA, Tendick SK, Terzis A, Strouse CE (1993) J Am Chem Soc 115:9480 22. Weber E, Czugler M (1988) Top Curr Chem 149:45 23. Miyata M, Sada K (1996) In: Lehn JM,Atwood JL, Davies JED, MacNicol DD,Vögtle F (eds) Comprehensive supramolecular chemistry, vol 6, chap 6. Pergamon Press, Oxford 24. Golberg I, Krupitsky H, Stein Z, Hsiou Y, Strouse CE (1995) Supramol Chem 4:203 25. Abrahams BF, Hoskins BF, Michail DM, Robson R (1994) Nature, 369:72 26. Su D, Wang X, Simard M, Wuest JD (1995) Supramol Chem 6:171 27. Desiraju GR (1997) J Chem Soc Chem Commun 1475 28. Desiraju GR (1995) Angew Chem Int Ed Engl 34:2311 29. Russel VA, Ward MD (1996) Chem Mater 8:1654 30. Russel VA, Evans CC, Li W, Ward MD (1997) Science 276:575 31. Ermer O (1988) J Am Chem Soc 110:3747 32. Ermer O, Eling A (1988) Angew Chem Int Ed Engl 27:829 33. Simard M, Su D, Wuest JD (1991) J Am Chem Soc 113:4696 34. Copp SB, Subramanian S, Zawarotko MJ (1992) J Am Chem Soc 114:8719 35. Hoskins BF, Robson R (1990) J Am Chem Soc 112:1546 36. Carlucci L, Ciani G, Proserpio DM, Sironi A (1994) J Chem Soc Chem Commun 1994:2755 37. Reddy DS, Craig DC, Rae D, Desiraju GR (1993) J Chem Soc Chem Commun 1993:1737 38. Ermer O, Lindenberg L (1991) Helv Chim Acta 74:825 39. Copp SB, Subramanian S, Zaworotko MJ (1993) J Chem Soc Chem Commun 1993:1078 40. Gable RW, Hoskins BF, Robson R (1990) J Chem Soc Chem Commun 1990:762 41. Gardner GB,Venkataraman D, Moore JS, Lee S (1995) Nature 374:792 42. Reddy DS, Craig DC, Desiraju GR (1995) J Chem Soc Chem Commun 1995:339 43. Abrahams BF, Hoskins BF, Robson R (1991) J. Am Chem Soc 113:3606 44. Fujita M, Kwon YJ, Washizu S, Ogura K (1994) J Am Chem Soc 116:1151 45. Venkataraman D, Gradner GB, Lee S, Moore JS (1995) J Am Chem Soc 117:11,600 46. Duchamp DJ, Marsh RE (1969) Acta Crystallogr B25:5 47. Venkataraman D, Lee S, Zhang J, Moore JS (1994) Nature 371:591 48. Kolotuchin SV, Felton EE, Wilson SR, Loweth CJ, Zimmerman SC (1995) Angew Chem Int Ed Engl 23:2654 49. Melendez RE, Sharma CVK, Zaworotko MJ, Bauer C, Rogers RD (1996) Angew Chem Int Ed Engl 24:2213
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198 Topics in Current Chemistry Edi
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Design of Organic Solids Volume Edi
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Volume Editors Prof. Dr. Edwin Webe
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VIII preface tion at an amazing lev
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Contents of Volume 196 Carbon Rich
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2 J.P. Glusker 5 Interactions of Pl
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4 J.P. Glusker Perturbations to the
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6 J.P. Glusker 2.1 Sources of Cryst
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8 J.P. Glusker other induced, will
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10 J.P. Glusker The forces here hav
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12 J.P. Glusker lographic structure
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14 J.P. Glusker a c Fig. 6 a - c. D
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16 J.P. Glusker hydrogen bond H◊
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18 J.P. Glusker Fig. 9. Citric acid
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20 J.P. Glusker peptide plane and a
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22 J.P. Glusker 4.5 F◊◊◊H Int
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28 J.P. Glusker bind to a metal ion
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30 J.P. Glusker As for carboxylate
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32 J.P. Glusker Fig. 24. The magnes
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34 J.P. Glusker structures of magne
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54 J.P. Glusker 23. Cody V, Murray-
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56 J.P. Glusker: Directional Aspect
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58 A. Nangia · G.R. Desiraju 7 Sup
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Springer and the environment At Spr
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