Energetics of guest binding to calix[4]arene molecular containers

Tetrahedron

Volumn 65, Issue 35, 2009, Pages 7259-7267

  Iwamoto, Hajime ^a   Niimi, Kahoru ^a   Haino, Takeharu ^a   Fukazawa, Yoshimasa ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; CALIXARENE; CATION; CHLOROFORM; INORGANIC COMPOUND; MACROCYCLIC COMPOUND; N METHYLPICOLINIUM SALT; PICOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; COMPLEX FORMATION; ENCAPSULATION; ENERGY TRANSFER; ENTHALPY; PRIORITY JOURNAL; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS; THERMODYNAMICS;

EID: 67651098713     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.01.021     Document Type: Article

References (120)

1. Cram D.J., and Cram J.M. Container Molecules and Their Guests (1997), Royal Society of Chemistry, Cambridge
2. Gutsche C.D. Calixarenes Revisited (1998), Royal Society of Chemistry, Cambridge
3. Rudkevich D.M. In: Schrader T., and Hamilton A.D. (Eds). Functional Synthetic Receptors (2005), Wiley-VCH, Weinheim pp 257-298
4. Cram D.J. Science 219 (1983) 1177-1183
5. Cram D.J. Nature 356 (1992) 29-36
6. Choi H.J., Cram D.J., Knobler C.B., and Maverick E.F. Pure Appl. Chem. 65 (1993) 539-543
7. Collet A., Dutasta J.P., Lozach B., and Canceill J. Top. Curr. Chem. 165 (1993) 103-129
8. Sherman J.C. Tetrahedron 51 (1995) 3395-3422
9. Collet A. Comp. Supramol. Chem. 2 (1996) 325-365
10. Maverick E., and Cram D.J. Comp. Supramol. Chem. 2 (1996) 367-418
11. Rebek Jr. J. Chem. Soc. Rev. 25 (1996) 255-264
12. Chapman R.G., and Sherman J.C. Tetrahedron 53 (1997) 15911-15945
13. Conn M.M., and Rebek Jr. J. Chem. Rev. 97 (1997) 1647-1668
14. Higler I., Timmermann P., Verboom W., and Reinhoudt D.N. Eur. J. Org. Chem. (1998) 2689-2702
15. Jasat A., and Sherman J.C. Chem. Rev. 99 (1999) 931-967
16. Rudkevich D.M., and Rebek Jr. J. Eur. J. Org. Chem. (1999) 1991-2005
17. Rudkevich D.M. Chem.-Eur. J. 6 (2000) 2679-2686
18. Warmuth R. J. Inclusion Phenom. Macrocyclic Chem. 37 (2000) 1-38
19. Prins L.J., Reinhoudt D.N., and Timmerman P. Angew. Chem., Int. Ed. 40 (2001) 2382-2426
20. Hof F., Craig S.L., Nuckolls C., and Rebek Jr. J. Angew. Chem., Int. Ed. 41 (2002) 1488-1508
21. Rebek Jr. J. Angew. Chem., Int. Ed. 44 (2005) 2068-2078
22. Cram D.J., Karbach S., Kim Y.H., Baczynskyj L., Marti K., Sampson R.M., and Kalleymeyn G.W. J. Am. Chem. Soc. 110 (1988) 2554-2560
23. Bryant J.A., Blanda M.T., Vincenti M., and Cram D.J. J. Am. Chem. Soc. 113 (1991) 2167-2172
24. Cram D.J., Tanner M.E., and Knobler C.B. J. Am. Chem. Soc. 113 (1991) 7717-7727
25. Cram D.J., Tanner M.E., and Thomas R. Angew. Chem., Int. Ed. Engl. 30 (1991) 1024-1027
26. Quan M.L.C., and Cram D.J. J. Am. Chem. Soc. 113 (1991) 2754-2755
27. Cram D.J., Blanda M.T., Paek K., and Knobler C.B. J. Am. Chem. Soc. 114 (1992) 7765-7773
28. Cram D.J., Jaeger R., and Deshayes K. J. Am. Chem. Soc. 115 (1993) 10111-10116
29. Robbins T.A., and Cram D.J. J. Am. Chem. Soc. 115 (1993) 12199
30. Byun Y.-S., Vadhat O., Blanda M.T., Knobler C.B., and Cram D.J. J. Chem. Soc., Chem. Commun. (1995) 1825-1827
31. Kurdistani S.K., Helgeson R.C., and Cram D.J. J. Am. Chem. Soc. 117 (1995) 1659-1660
32. Yoon J., Sheu C., Houk K.N., Knobler C.B., and Cram D.J. J. Org. Chem. 61 (1996) 9323-9339
33. Helgeson R.C., Knobler C.B., and Cram D.J. J. Am. Chem. Soc. 119 (1997) 3229-3244
34. Branda N., Grotzfeld R.M., Valdes C., and Rebek Jr. J. J. Am. Chem. Soc. 117 (1995) 85-88
35. Meissner R.S., Rebek Jr. J., and de Mendoza J. Science 270 (1995) 1485-1488
36. Shimizu K.D., and Rebek Jr. J. Proc. Natl. Acad. Sci. U.S.A. 92 (1995) 12403-12407
37. Hamann B.C., Shimizu K.D., and Rebek Jr. J. Angew. Chem., Int. Ed. 35 (1996) 1326-1329
38. O'Leary B.M., Grotzfeld R.M., and Rebek Jr. J. J. Am. Chem. Soc. 119 (1997) 11701-11702
39. Rivera J.M., Martin T., and Rebek Jr. J. J. Am. Chem. Soc. 120 (1998) 819-820
40. Heinz T., Rudkevich D.M., and Rebek Jr. J. Angew. Chem., Int. Ed. 38 (1999) 1136-1139
41. Tucci F.C., Rudkevich D.M., and Rebek Jr. J. J. Am. Chem. Soc. 121 (1999) 4928-4929
42. O'Leary B.M., Szabo T., Svenstrup N., Schalley C.A., Luetzen A., Schaefer M., and Rebek Jr. J. J. Am. Chem. Soc. 123 (2001) 11519-11533
43. Shivanyuk A., and Rebek Jr. J. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 7662-7665
44. Hof F., and Rebek Jr. J. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 4775-4777
45. Johnson D.W., Hof F., Iovine P.M., Nuckolls C., and Rebek Jr. J. Angew. Chem., Int. Ed. 41 (2002) 3793-3796
46. Iwasawa T., Ajami D., and Rebek Jr. J. Org. Lett. 8 (2006) 2925-2928
47. Böhmer V., Goldman G., Vogt W., Vicens J., and Asfari Z. Tetrahedron Lett. 30 (1989) 1391-1394
48. Arduini A., Manfredi G., Pochini A., Sicuri A.R., and Ungaro R. J. Chem. Soc., Chem. Commun. (1991) 936-937
49. Perez-Adelmar J.-A., Abraham H., Sanchez C., Rissanen K., Prados P., and de Mendoza J. Angew. Chem., Int. Ed. 35 (1996) 1009-1011
50. Jorgensen M., Larsen M., Sommer-Larsen P., Petersen W.B., and Eggert H. J. Chem. Soc., Perkin Trans. 1 (1997) 2851-2855
51. Neri P., Bottino A., Cunsolo F., Piattelli M., and Gavuzzo E. Angew. Chem., Int. Ed. 37 (1998) 166-169
52. Hardie M.J., Makha M., and Raston C.L. Chem. Commun. (1999) 2409-2410
53. Shivanyuk A., Paulus E.F., and Böhmer V. Angew. Chem., Int. Ed. 38 (1999) 2906-2909
54. Hwang G.T., and Kim B.H. Tetrahedron Lett. 41 (2000) 5917-5921
55. Wang J., Bodige S.G., Watson W.H., and Gutsche C.D. J. Org. Chem. 65 (2000) 8260-8263
56. Araki K., and Hayashida H. Tetrahedron Lett. 41 (2000) 1209-1213
57. Araki K., Watanabe T., Oda M., Hayashida H., Yasutake M., and Shinmyozu T. Tetrahedron Lett. 42 (2001) 7465-7468
58. Cave G.W.V., Hardie M.J., Roberts B.A., and Raston C.L. Eur. J. Org. Chem. (2001) 3227-3231
59. Zadmard R., Schrader T., Grawe T., and Kraft A. Org. Lett. 4 (2002) 1687-1690
60. Moon K., and Kaifer A.E. J. Am. Chem. Soc. 126 (2004) 15016-15017
61. Arimura T., Matsumoto S., Teshima O., Nagasaki T., and Shinkai S. Tetrahedron Lett. 32 (1991) 5111-5114
62. Araki K., Sisido K., Hisaichi K., and Shinkai S. Tetrahedron Lett. 34 (1993) 8297-8300
63. Fujimoto K., and Shinkai S. Tetrahedron Lett. 35 (1994) 2915-2918
64. Koh K., Araki K., and Shinkai S. Tetrahedron Lett. 35 (1994) 8255-8258
65. Ikeda A., and Shinkai S. J. Chem. Soc., Chem. Commun. (1994) 2375-2376
66. Araki K., Hisaichi K., Kanai T., and Shinkai S. Chem. Lett. (1995) 569-570
67. Zhong Z., Ikeda A., and Shinkai S. J. Am. Chem. Soc. 121 (1999) 11906-11907
68. Timmerman P., Verboom W., van Veggel F.C.J.M., van Hoorn W.P., and Reinhoudt D.N. Angew. Chem., Int. Ed. Engl. 33 (1994) 1292-1295
69. Timmerman P., Verboom W., van Veggel F.C.J.M., van Duynhoven J.P.M., and Reinhoudt D.N. Angew. Chem., Int. Ed. Engl. 106 (1994) 2437-2440
70. Timmerman P., Nierop K.G.A., Brinks E.A., Verboom W., van Veggel F.C.J.M., van Hoorn W.P., and Reinhoudt D.N. Chem.-Eur. J. 1 (1995) 132-143
71. van Wageningen A.M.A., van Duynhoven J.P.M., Verboom W., and Reinhoudt D.N. J. Chem. Soc., Chem. Commun. (1995) 1941-1942
72. Struck O., Chrisstoffels L.A.J., Lugtenberg R.J.W., Verboom W., van Hummel G.J., Harkema S., and Reinhoudt D.N. J. Org. Chem. 62 (1997) 2487-2493
73. van Wageningen A.M.A., Timmerman P., van Duynhoven J.P.M., Verboom W., van Veggel F.C.J.M., and Reinhoudt D.N. Chem.-Eur. J. 3 (1997) 639-654
74. Corbellini F., Di Costanzo L., Crego-Calama M., Geremia S., and Reinhoudt D.N. J. Am. Chem. Soc. 125 (2003) 9946-9947
75. Oshovsky G.V., Reinhoudt D.N., and Verboom W. Eur. J. Org. Chem. (2006) 2810-2816
76. Haino T., Yanase M., and Fukazawa Y. Angew. Chem., Int. Ed. 37 (1998) 997-998
77. Yanase M., Haino T., and Fukazawa Y. Tetrahedron Lett. 40 (1999) 2781-2784
78. Haino T., Araki H., Yamanaka Y., and Fukazawa Y. Tetrahedron Lett. 42 (2001) 3203-3206
79. Haino T., Araki H., Fujiwara Y., Tanimoto Y., and Fukazawa Y. Chem. Commun. (2002) 2148-2149
80. Haino T., Yamanaka Y., Araki H., and Fukazawa Y. Chem. Commun. (2002) 402-403
81. Iwamoto H., Yukimasa Y., and Fukazawa Y. Tetrahedron Lett. 43 (2002) 8191-8194
82. Haino T., Nakamura M., Kato N., Hiraoka M., and Fukazawa Y. Tetrahedron Lett. 45 (2004) 2281-2284
83. Haino T., Matsumoto Y., and Fukazawa Y. J. Am. Chem. Soc. 127 (2005) 8936-8937
84. Haino T., Kobayashi M., Chikaraishi M., and Fukazawa Y. Chem. Commun. (2005) 2321-2323
85. Haino T., Seyama J., Fukunaga C., Murata Y., Komatsu K., and Fukazawa Y. Bull. Chem. Soc. Jpn. 78 (2005) 768-770
86. Haino T., Fukunaga C., and Fukazawa Y. Org. Lett. 8 (2006) 3545-3548
87. Haino T., Nakamura M., and Fukazawa Y. Heterocycles 68 (2006) 2477-2482
88. Haino T., Fukunaga C., and Fukazawa Y. Org. Lett. 8 (2006) 3545-3548
89. Haino T., Kobayashi M., and Fukazawa Y. Chem.-Eur. J. 12 (2006) 3310-3319
90. Haino T., Yanase M., Fukunaga C., and Fukazawa Y. Tetrahedron 62 (2006) 2025-2035
91. Haino T., Fukuoka H., Katayama M., and Fukazawa Y. Chem. Lett. 36 (2007) 1054-1055
92. Haino T., Fukunaga C., and Fukazawa Y. J. Nanosci. Nanotechnol. 7 (2007) 1386-1388
93. Haino T., Fukuoka H., Iwamoto H., and Fukazawa Y. Supramol. Chem. 20 (2008) 51-57
94. Haino T., Hirakata M., Niimi K., Kouchi M., Iwamoto H., and Fukazawa Y. Chem. Lett. 37 (2008) 394-395
95. Haino T., Akii H., and Fukazawa Y. Synlett (1998) 1016-1018
96. Timmerman P., Boerrigter H., Verboom W., and Reinhoudt D.N. Recl. Trav. Chim. Pays-Bas 114 (1995) 103-111
97. Connors K.A. Binding Constants (1987), John Wiley & Sons, New York, NY
98. Leggett D.J. Computational Methods for the Determination of Formation Constants. Modern Inorganic Chemistry Series (1985), Plenum, New York, NY
99. Inoue Y., and Hakushi T. J. Chem. Soc., Perkin Trans. 2 (1985) 935-946
100. Inoue Y., Amano F., Okada N., Inada H., Ouchi M., Tai A., Hakushi T., Liu Y., and Tong L. J. Chem. Soc., Perkin Trans. 2 (1990) 1239-1246
101. Counter anion effect can be seen in the following literatures:
102. De Iasi G., and Masci B. Tetrahedron Lett. 34 (1993) 6635-6638
103. Arduini A., McGregor W.M., Paganuzzi D., Pochini A., Secchi A., Ugozzoli F., and Ungaro R. J. Chem. Soc., Perkin Trans. 2 (1996) 839-846
104. Arnecke R., Böhmer V., Cacciapaglia R., Dalla Cort A., and Mandolini L. Tetrahedron 53 (1997) 4901-4908
105. Kubik S., and Goddard R. Chem. Commun. (2000) 633-634
106. Böhmer V., Dalla Cort A., and Mandolini L. J. Org. Chem. 66 (2001) 1900-1902
107. Stabilization energies were obtained as the difference between the total energy of the ion-pairs and the sum of the independently optimized energies of the individual ions.
108. Spartan'06, Wavefunction, Inc., Irvine, CA, 2006.
109. Donati D., Roelens S., Torriti R., and Valle G. Aust. J. Chem. 51 (1998) 361-369
110. Roelens S., and Torriti R. J. Am. Chem. Soc. 120 (1998) 12443-12452
111. Bartoli S., and Roelens S. J. Am. Chem. Soc. 121 (1999) 11908-11909
112. Roelens S., and Torriti R. Supramol. Chem. 10 (1999) 225-232
113. Bartoli S., and Roelens S. J. Am. Chem. Soc. 124 (2002) 8307-8315
114. Harrison J.C., and Eftink M.R. Biopolymers 21 (1982) 1153-1166
115. Diederich F., Smithrud D.B., Sanford E.M., Wyman T.B., Ferguson S.B., Carcanague D.R., Chao I., and Houk K.N. Acta Chem. Scand. 46 (1992) 205-215
116. Zhang B., and Breslow R. J. Am. Chem. Soc. 115 (1993) 9353-9354
117. Tobey S.L., and Anslyn E.V. J. Am. Chem. Soc. 125 (2003) 14807-14815
118. Kano K., Ishida Y., Kitagawa K., Yasuda M., and Watanabe M. Chem. Asian J. 2 (2007) 1305-1313
119. Bonar-Law R.P., and Sanders J.K.M. J. Am. Chem. Soc. 117 (1995) 259-271
120. Hayashi T., Miyahara T., Koide N., Kato Y., Masuda H., and Ogoshi H. J. Am. Chem. Soc. 119 (1997) 7281-7290