Reflections on the construction of anion receptors. Is there a sign to resign from design?

Coordination Chemistry Reviews

Volumn 250, Issue 23-24, 2006, Pages 2918-2928

  Schmidtchen, Franz P ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Anion receptor; Association entropy; Host guest design; Molecular recognition; Selectivity

Indexed keywords

EID: 33750518857     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2006.07.009     Document Type: Review

References (91)

1. 26,000,000,000,000,000,000 microstates even at very low temperature (T < 4 K, K.S. Pitzer, Thermodynamics, 3rd ed., McGraw-Hill, New York, 1995, p. 67; cf. E.I. Kozliak, F. Lambert, Chem. Educator 10 (2005) 24). The fraction among these microstates that form equilibrium arrangements of all atoms and are indeed populated at room temperature may be substantially smaller. Even though, their number will still be immense preventing any testing of the individual cases. We believe, thus, that there is room enough for knowledge, intuition, experience and sensible feeling in the construction of molecular receptors to justify the term "design" as it relates to an act of creativity.
2. For pertinent summaries see:
3. Sessler J.L., Gale P.A., and Cho W.-S. Anion Receptor Chemistry (2006), RCS Publishing, Cambridge
4. In: Bianchi A., Bowman-James K., and García-Espana E. (Eds). Supramolecular Chemistry of Anions (1997), Wiley-VCH, New York
5. Kubik S., Reyheller C., and Stuewe S. J. Inclus. Macrocycl. Chem. 52 (2005) 137
6. Beer P.D., and Gale P.A. Angew. Chem. Int. Ed. 40 (2001) 486
7. Schmidtchen F.P., and Berger M. Chem. Rev. 97 (1997) 1609
8. Schmidtchen F.P. Angew. Chem. Int. Ed. Engl. 16 (1977) 720
9. Schmidtchen F.P. Top. Curr. Chem. 255 (2005) 1
10. Bianchi A., and García-Espana E. Thermodynamics of anion complexation. In: Bianchi A., Bowman-James K., and García-Espana E. (Eds). Supramolecular Chemistry of Anions (1997), Wiley-VCH, New York 217
11. Schmidtchen F.P. Thermodynamic and kinetic selectivity. In: Atwood J. (Ed). Encyclopedia of Supramolecular Chemistry (2004), Marcel Dekker, New York 1225
12. Rao J., Lahiri J., Weis R.M., and Whitesides G.M. J. Am. Chem. Soc. 122 (2000) 2698
13. Timasheff S.N. Biophys. Chem. 101/102 (2002) 99
14. Schellman J.A. Biophys. Chem. 96 (2002) 91
15. Ben-Naim A. Biophys. Chem. 101/102 (2002) 309
16. Ben-Naim A. Biophys. Chem. 105 (2003) 183
17. Gohlke H., and Klebe G. Angew. Chem. Int. Ed. 41 (2002) 2644
18. van Gunsteren W.F., Bakowies D., Baron R., Chandrsekhar I., Christen M., Daura X., Gee P., Geerke D.P., Glättli A., Hünenberger P.H., Kastenholz M.A., Oostenbrink C., Schenk M., Trzesniak D., van der Vegt N.F.A., and Yu H.B. Angew. Chem. Int. Ed. 45 (2006) 4064
19. Pratt L.R. Ann. Rev. Phys. Chem. 53 (2002) 409
20. Moelbert S., and De Los Rios P. J. Chem. Phys. 119 (2003) 7988
21. Yasuda S., Suzuki I., Shinohara K.-I., and Shigekawa H. Phys. Rev. Lett. 96 (2006) 228303
22. For an early example of making use of solvophobic binding in artificial hosts see:. Cram D.J., Choi H.-J., Bryant J.A., and Knobler C.B. J. Am. Chem. Soc. 114 (1992) 7748
23. Lipkowitz cf.K.B. J. Chem. Educ. 72 (1995) 1070
24. Adcock S.A., and McCammon J.A. Chem. Rev. 106 (2006) 1589
25. For illustrative examples see:
26. Glättli A., and van Gunsteren W.F. Angew. Chem. Int. Ed. 43 (2004) 6312
27. Barron R., Bakowies D., and van Gunsteren W.F. J. Pept. Sci. 11 (2005) 74
28. Trzesniak D., Glättli A., Jaun B., and van Gunsteren W.F. J. Am. Chem. Soc. 127 (2005) 14320
29. Chang C.-E., and Gilson M.K. J. Am. Chem. Soc. 126 (2004) 13156
30. Uversky V.N., Oldfield C.J., and Dunker A.K. J. Molec. Recognit. 18 (2005) 343
31. Hopkins A.L., Mason J.S., and Overngton J.P. Curr. Opin. Struct. Biol. 16 (2006) 127
32. Fink A.L. Curr. Opin. Struct. Biol. 15 (2005) 35
33. Copley S.D. Curr. Opin. Chem. Biol. 7 (2003) 265
34. McPherson A. BioEssays 27 (2005) 447
35. Csiszár A. BioEssays 28 (2006) 465
36. Verma C.S., and Fischer S. Biophys. Chem. 115 (2005) 295
37. Williams D.H., Zhou M., and Stephens E. J. Mol. Biol. 355 (2006) 760
38. Williams D.H., Calderone C.T., O'Brien D.P., and Zerella R. Chem. Commun. (2002) 1266
39. Williams D.H., O'Brien D.P., Sandercock A.M., and Stephens E. J. Mol. Biol. 340 (2004) 373
40. Williams D.H., Davies N.L., Zeralla R., and Bardsley B. J. Am. Chem. Soc. 126 (2004) 2042
41. Dill K.A. J. Biol. Chem. 272 (1997) 01
42. De Robertis A., De Stefano C., Giuffre O., and Sammartano S. Ann. Chim. 89 (1999) 23
43. Fischer E. Chem. Ber. 27 (1894) 2985
44. Jones J.W., and Gibson H.W. J. Am. Chem. Soc. 125 (2003) 7001
45. Jones J.W., Huang F., Bryant W.S., and Gibson H.W. J. Am. Chem. Soc. 45 (2004) 5961
46. Huang F., Jones J.W., Slebodnik C., and Gibson H.W. J. Am. Chem. Soc. 125 (2003) 14458
47. Camiolo S., Gale P.A., Hursthouse M.B., and Light M.E. Org. Biomol. Chem. 1 (2003) 741
48. Ercolani G. Org. Lett. 7 (2005) 803
49. Ercolani G. J. Phys. Chem. B 107 (2003) 5052
50. Ercolani G. J. Am. Chem. Soc. 125 (2003) 16097
51. Schmidtchen F.P. Angew. Chem. Int. Ed. Engl. 20 (1981) 466
52. Schmidtchen F.P. Chem. Ber. 117 (1984) 1287
53. Schmidtchen F.P. J. Mol. Catal. 37 (1986) 141
54. Schmidtchen F.P. Top. Curr. Chem. 132 (1986) 101
55. Williams D.H., Stephens E., O'Brien D.P., and Zhou M. Angew. Chem. Int. Ed. 43 (2004) 6596
56. Blades A.T., and Kebarle P. Can. J. Phys. Chem. A 109 (2005) 8293
57. Schroeder D. Angew. Chem. Int. Ed. 43 (2004) 1329
58. Chapman K.T., and Still W.C. J. Am. Chem. Soc. 111 (1989) 3075
59. Bowman-James K. Acc. Chem. Res. 38 (2005) 671
60. Kubik S. Cyclopeptides as macrocyclic host molecules for charged guests. In: Schmuck C., and Wennemers H. (Eds). Highlights in Bioorganic Chemistry (2005), Wiley-VCH, Weinheim 124
61. Suksai C., and Tuntulani T. Top. Curr. Chem. 255 (2005) 163
62. An increase in order does not necessarily involve a diminution of entropy, see:
63. Lekkerkerker H.N.W., and Stroobants A. Nature 393 (1998) 305
64. Adams M., Dogic Z., Keller S.L., and Fraden S. Nature 393 (1998) 349
65. Schneider H.J., Ruediger V., and Raevsky O.A. J. Org. Chem. 58 (1993) 3648
66. Bazzicalupi C., Bencini A., Bianchi A., Cecchi M., Escuder B., Fusi V., Garcia-espana E., Giorgi C., Luis S.V., Maccagni G., Marcelino V., Paoletti P., and Valtancoli B. J. Am. Chem. Soc. 121 (1999) 6807
67. Berger M., and Schmidtchen F.P. Angew. Chem. Int. Ed. 37 (1998) 2694
68. Berger M., and Schmidtchen F.P. J. Am. Chem. Soc. 118 (1996) 8947
69. Berger M., and Schmidtchen F.P. J. Am. Chem. Soc. 121 (1999) 9986
70. Mason P.E., Dempsey C.E., Neilson G.W., and Brady J.W. J. Phys. Chem. B 109 (2005) 24185
71. Bryant J.A., Ericson J.L., and Cram D.J. J. Am. Chem. Soc. 112 (1990) 1255
72. Jadhav V.D., and Schmidtchen F.P. Org. Lett. 11 (2005) 331
73. Ercolani G. J. Org. Chem. 64 (1999) 3350
74. Tobey S.L., and Anslyn E.V. J. Am. Chem. Soc. 125 (2003) 14807
75. Wiskur S.L., Lavigne J.J., Metzger A., Tobey S.L., Lynch V., and Anslyn E.V. Chem. Eur. J. 10 (2004) 3792
76. Tobey S.L., and Anslyn E.V. J. Am. Chem. Soc. 125 (2003) 10963
77. For a lucid discussion of the dissection of thermodynamic state functions see:
78. Williams D.H., and Westwell M.S. Chem. Soc. Rev. 27 (1998) 57
79. Williams D.H., Stephens E., and Zhou M. Chem. Commun. (1973-1976) and earlier work of these authors
80. Lu B., and Wong C.F. Biopolymers 79 (2005) 277
81. Murray C.W., and Verdonk M.L. J Comp. Aid. Mol. Design 16 (2002) 741
82. Yu B.Y., Privalov P.L., and Hodges R.S. Biophys. J. 81 (2001) 1632
83. Dunitz J.D. Chem. Biol. 2 (1995) 709
84. Chen W., Chang C.-E., and Gilson M.K. Biophys. J. 87 (2004) 3035
85. García-Pérez M., Pinto M., and Subirana J.A. Biopolymers 69 (2003) 432
86. Haj-Zaroubi M., Mitzel N.W., and Schmidtchen F.P. Angew. Chem. Int. Ed. 41 (2002) 104
87. Haj-Zaroubi M., and Schmidtchen F.P. Chem. Phys. Chem 6 (2005) 1181
88. Christen M., Hunenberger P.H., Bakowies D., Baron R., Burgi R., Geerke D.P., Heinz T.N., Kastenholz M.A., Krautler V., Oostenbrink C., Peter C., Trzesniak D., and van Gunsteren W.F. J. Comp. Chem. 26 (2005) 1719
89. Hsu S.-T.D., Peter C., van Gunsteren W.F., and Bonvin A.M.J.J. Biophys. J. 88 (2005) 15
90. Mardis K.L. J. Phys. Chem. B 110 (2006) 971
91. A. Einstein, cited after: http://www.janko.at/Zitate/Autoren/Einstein.htm.