Computational studies on two supramolecular structures: Cyclodextrins and rotaxanes

Current Organic Chemistry

Volumn 10, Issue 7, 2006, Pages 731-743

  Jaime, Carlos ^a   de Federico, Miguel ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

Cyclodextrine; Cyclodiastereomeric 3 rotaxanes; Enantiodifferentiation; MD simulations; Monosubstituted benzene; NMR

Indexed keywords

MOLECULES; SUPRAMOLECULAR CHEMISTRY;

COMPUTATIONAL STUDIES; COMPUTATIONAL TECHNIQUE; CYCLODEXTRINES; CYCLODIASTEREOMERIC [3]ROTAXANE; ENANTIO-DIFFERENTIATION; MD SIMULATION; MONOSUBSTITUTED BENZENES; ROTAXANES; SUPRAMOLECULAR SPECIES; SUPRAMOLECULAR STRUCTURE;

CYCLODEXTRINS;

1 BROMOADAMANTANE; 4 HYDROXYBENZOIC ACID ESTER; ACETONITRILE; ADAMANTANE; ADAMANTANE DERIVATIVE; ADAMANTANONE; ALICYCLIC HYDROCARBON; ALKANE DERIVATIVE; ALPHA CYCLODEXTRIN; ANTHRACENE DERIVATIVE; BENZAMIDE DERIVATIVE; BENZENE DERIVATIVE; BENZIDINE; BENZOIC ACID; BENZOIC ACID DERIVATIVE; BETA CYCLODEXTRIN; CARBOXYLIC ACID DERIVATIVE; CYCLODEXTRIN; CYCLOHEXANE DERIVATIVE; DECALIN DERIVATIVE; GAMMA CYCLODEXTRIN; NAPHTHALENE DERIVATIVE; PHENOL DERIVATIVE; ROTAXANE; UNCLASSIFIED DRUG;

CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; COMPUTER PROGRAM; CONFORMATIONAL TRANSITION; CONSTANTS AND COEFFICIENTS; COVALENT BOND; DIASTEREOISOMER; ENANTIOMER; GEOMETRY; MATHEMATICAL COMPUTING; MATHEMATICAL MODEL; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR STABILITY; REVIEW; SUPRAMOLECULAR CHEMISTRY;

EID: 33646520874     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527206776818900     Document Type: Review

References (106)

1. Cramer, F. Angew. Chem., 1956, 68, 115.
2. Bergeron, R.; Channing, M.; Gibeily, G.; Pillor, D. J. Am. Chem. Soc., 1977, 99, 5146.
3. Cramer, F.; Dietsche, W. Chem. Ber., 1959, 92, 378.
4. Harata, K. J. Chem. Soc., Perkin Trans. 2, 1990, 799.
5. Rees, D. J. Chem. Soc. B., 1970, 877.
6. Tabushi, I.; Kuroda, Y.; Mizutani, T. J. Am. Chem. Soc., 1986, 108, 4514.
7. Manor, P.; Saenger, W. J. Am. Chem. Soc, 1974, 96, 3630.
8. Saenger, W.; Noltenmeyer, M. Angew. Chem. Int. Ed. Engl., 1974, 13, 552.
9. Hingerty, B.; Saenger, W. J. Am. Chem. Soc., 1976, 98, 3357.
10. Tabushi, I.; Kiyosuke, Y.-I.; Sugimoto, T.; Yamamura, K. J. Am. Chem. Soc. 1978, 100, 916.
11. Schill, G. Catenanes, Rotaxanes and Knots; Academic Press: New York, 1971.
12. Villiers, A. C. R. Acad. Sci., 1891, 112, 536.
13. Osajima, T.; Deguchi, T.; Sanemasa, I. Bull. Chem. Soc. Jpn., 1991, 64, 2705.
14. Dunbar, R.A.; Bright, F.V. Supramol. Chem., 1993, 3, 93.
15. Blyshack, L.A.; Dodson, K.Y.; Patonay, G.; Warner, I.M. J. Am. Chem. Soc., 1989, 111, 955.
16. Hirsch, W.; Choy, C.K.; Ng, K.W.; Fried, V. Anal. Lett., 1989, 2861.
17. Tong, L.-H.; Hou, Z.-J.; Yoshihisa, I.; Akira, T. J. Chem. Soc. Perkin Trans. 2, 1992, 1253.
18. De Fontaine, D.L.; Ross, D.K.; Ternal, B. J. Phys. Chem., 1977, 81, 792.
19. Job, P. Ann. Chim., 1928, 9, 113.
20. Duchêne, D. Ed. New Trends in Cyclodextrins and Derivatives; Editions de Santé: Paris, 1993.
21. Lipkowitz, K.B. Chem. Rev., 1998, 98, 1829.
22. Redondo, J.; Jaime, C.; Virgili, A.; Sánchez-Ferrando, F. J. Molec. Struct., 1991, 248, 6521.
23. Sánchez-Ruiz, X.; Alvarez-Larena, A.; Jaime, C.; Piniella, J.F.; Redondo, J.; Virgili, A.; Sánchez-Ferrando, F.; Germain, G.; Baert, F. Supramol. Chem., 1999, 10, 219.
24. Jaime, C.; Redondo, J.; Sánchez-Ferrando, F.; Virgili, A. J. Org. Chem., 1990, 55, 4773;
25. b) Ivanov, P.; Jaime, C. Anales de Química, Int. Ed., 1996, 92, 13;
26. c) Ivanov, P.M.; Jaime, C. J. Molec. Struc., 1996, 377, 137;
27. Ivanov, P.; Salvatierra, D.; Jaime, C. J. Org. Chem., 1996, 61, 7012.
28. Salvatierra, D.; Jaime, C.; Virgili, A.; Sánchez-Ferrando, F. J. Org. Chem., 1996, 61, 9578.
29. Zubiaur, M.; Jaime, C. J. Org. Chem., 2000, 65, 8139.
30. Szejtli, J. Cyclodextrin and their Inclusion Complexes; Akadémiai Kiadó: Budapest, 1982;
31. b) Szejtli, J. Cyclodextrin technology; Kluwer Academic Publishers: Dordrecht, 1988.
32. Schill, G.; Rissler, K.; Fritz, H.; Vetter, W. Angew. Chem. Int. Ed. Engl., 1981, 20, 187.
33. Kotake, Y.; Janzen, E.G. J. Am. Chem. Soc., 1989, 111, 2066, 5138, and 7319;
34. b) Kotake, Y.; Janzen, E. G. J. Am. Chem. Soc., 1994, 114, 2872.
35. Fotiadu, F.; Fathallah, M.; Jaime, C. J. Org. Chem., 1994, 59, 1288;
36. b) Pérez, F.; Jaime, C; Sánchez-Ruiz, X. J. Org. Chem., 1995, 60, 3840.
37. Cervelló, E.; Jaime, C. J. Molec. Struct. (THEOCHEM), 1998, 428, 195.;
38. b) Cervelló, E.; Jaime, C. Anales de Quím. It. Ed., 1998, 4-5, 244;
39. c) Cervelló, E.; Mazzucchi, F.; Jaime, C. J. Molec. Struct. (THEOCHEM), 2000, 530, 155.
40. Sanemasa, Y. Wu, Y. Koide, M. Shigenaga, K. Ishibashi, T. Deguchi, Bull. Chem. Soc. Jpn., 1993, 66, 1424.
41. Sanemasa, T. Osajima, T. Deguchi, Bull. Chem. Soc. Jpn., 1990, 63, 2814.
42. Imashiro, F.; Maeda, T.; Nakai, T.; Saika, A.; Terao, T. J. Phys. Chem., 1986, 90, 5498.
43. Imashiro, F.; Kuwahara, D.; Nakai, T.; Terao, T. J. Chem. Phys., 1989, 90, 3356.
44. Shannon, I.J.; Harris, K.D.M.; Rennie, A.J.O.; Webster, M.B. J. Chem. Soc. Faraday Trans., 1993, 89, 2023.
45. Schofield, P.A.; Harris, K.D.M.; Shannon, I.J.; Rennie, A.J.O. J. Chem. Soc., Chem. Commun., 1993, 1293.
46. Müller, K. Magn. Reson. Chem., 1995, 33, 113.
47. Cannarozi, G.M.; Meresi, G.H.; Vold, R.L.; Vold, R.R. J. Phys. Chem., 1991, 95, 1525.
48. Sánchez-Ruiz, X.; Ramos, M.; Jaime, C. J. Molec. Struct., 1998, 442, 93.
49. Caira, M.R.; Vivienne, J.G.; Nassimbeni, L.R.; van Oudtshoorn, B. J. Chem. Soc. Perkin Trans 2, 1994, 2071.
50. Betzel, C.; Saenger, W.; Hingerty, B.E.; Brown, G.M. J. Am. Chem. Soc., 1984, 106, 7545.
51. Steiner, T.; Mason, S.A.; Saenger, W. J. Am. Chem. Soc., 1991, 113, 5676.
52. Koehler, K.E.H.; Saenger, W.; van Gusteren, W.F. J. Mol. Biol., 1988, 203, 241.
53. Dodziuk, H.; Nowinski, K. J. Mol. Struct. (Theochem), 1994, 304, 61.
54. Tanabe, T.; Kishimoto, S.; Maruyama, S.; Kumon, S.; Suzuki, E.; Perly, B.; Keller, N.; Charpin, P. Supramol. Chem., 1994, 3, 127.
55. Schurig, V.; Nowotny, H.-P.; Schmalzing, D. Angew, Chem. Int. Ed. Engl., 1989, 28, 736.
56. Fotiadu, F.; Fathallah, M.; Jaime, C. J. Inc. Phenom., 1993, 16, 55.
57. Lipkowitz, K.B.; Coner, B.; Peterson, M.A.; Morreale, A. J. Org. Chem., 1998, 63, 732.
58. Neuhaus, D.; Williamson, M. The Nuclear Overhauser Effect in Structural and Conformational Analysis; VCH: New York, 1989.
59. Mark, A.E.; van Helden, S.P.; Smith, P.E.; Cansen, L.H.M.; van Gunsteren, W.F. J. Am. Chem. Soc., 1994, 116, 6239.
60. Salvatierra, D.; Sánchez-Ruiz, X.; Garduño, R.; Cervelló, E.; Jaime, C.; Virgili, A.; Sánchez-Ferrando, F. Tetrahedron, 2000, 56, 3035.
61. Beà, I.; Jaime, C.; Redondo, J.; Bonnet, P.; Torrens, A.; Frigola, J. Supramolecular Chem., 2001, 14, 33.
62. Ramamurthy, V.; Eaton, D.F. Acc. Chem. Ress., 1988, 21, 300.
63. Syamala, M.S.; Rao, B.N. Ramamurthy, V. Tetrahedron, 1988, 62, 914.
64. Breslow, R.; Guo, T. J. Am. Chem. Soc., 1988, 110, 5613.
65. Schneider, H.J.; Sangwan, N.K. Angew. Chem. Int. Ed. Engl., 1987, 26, 896.
66. Komimaya, M.; Hirai, H. J. Am. Chem. Soc., 1988, 45, 17.
67. Mehta, G.; Khan, F.A.; Lakshmi, A. Tetrahedron Lett., 1992, 7977.
68. Chung, W.S.; Turro, N.J.; Silver, J.; le Noble, W.J. J. Am. Chem. Soc., 1990, 112, 1202.
69. Entrena, A.; Jaime, C. J. Org. Chem., 1997, 62, 5923.
70. Fernández, M.A.; de Rossi, R.H.; Cervelló, E.; Jaime, C. J. Org. Chem., 1991, 66, 4399.
71. Fernández, M.A.; de Rossi R. H. J. Org. Chem., 1997, 62, 7554
72. Milioto, S.; Crisantino, R.; Delisi, R.; Inglese, A. Langmuir, 1995, 11, 718.
73. Bonnet, P.; Jaime, C.; Morin-Allory, L. J. Org. Chem., 2001, 66, 689.
74. Bonnet, P.; Jaime, C.; Morin-Allory, L. J. Org. Chem., 2002, 67, 8602.
75. Bonnet, P.; Beà, I.; Jaime, C.; Morin-Allory, L. Supramol. Chem., 2002, 14, 33.
76. Lino, A.C.S.; Takahata, Y.; Jaime, C. J. Molec. Struct. (THEOCHEM), 2002, 594, 207.
77. Lino, A.C.S.; Loh, W. J. Inc. Phenom., 2000, 36, 267.
78. Beà, I.; Jaime, C.; Kollman, P.A. Theor. Chem. Acc., 1992, 108, 286.
79. Breslow, R.; Greenspoon, N.; Guo, T.; Zarzycki, R. J. Am. Chem. Soc., 1989, 111, 8296.
80. Beà, I.; Cervelló, E.; Kollman, P.A.; Jaime, C. Comb. Chem and High Throughput Screeening, 2001, 4, 605.
81. Schill, G.; Zollekopf, H. Liebigs Ann. Chem., 1967, 721, 53.
82. Harrison, I.T.; Harrison, S. J. Am. Chem. Soc., 1967, 89, 5723.
83. Dietrich-Bucheker, C.; Sauvage, J.P.; Kintzinter, J.P. Tetrahedron Lett., 1983, 24, 5098.
84. Ogino, H. J. Am. Chem. Soc., 1981, 103, 1303.
85. F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann., 1995, 739.
86. Bissell, R.A.; Córdova, E.; Kaifer, A.E.; Stoddart, J.F. Nature, 1994, 369, 133.
87. As examples see: a) Amabilino, D.B.; Asakawa, M.; Ashton, P.R.; Ballardini, R.; Balzani, V.; Belohradsky, M.; Credi, A.; Higuchi, M.; Raymo, F.M.; Shimizu, T.; Stoddart, J.F.; Venturi, M.; Yase, K. New. J. Chem., 1998, 959;
88. b) Ashton, P.R.; Boyd, S.E.; Menzer, S.; Pasini, D.; Raymo, F.M.; Spencer, N.; Stoddart, J.F.; White, A.J.P.; Williams, D.J.; Wyatt, P.G. Chem. Eur. J., 1998, 4, 299.
89. a) Mayer, B.; Klein, C.T.; Topchieva, I.N.; Kohler, G. J. Comp. Aid. Mol. Desing, 1999, 13, 373;
90. b) Pozuelo, J.; Mendicuti, F.; Saiz, E. Polymer, 2001, 43, 523;
91. c) Pozuelo, J.; Mendicuti, F.; Mattice, W.L. Polymer Journal, 1998, 30, 479;
92. d) Pozuelo, J.; Mendicuti, F.; Mattice, W.L. Macromolecules, 1997, 30, 3685;
93. e) Horsky, J. Macromol. Theory and Simulations, 2000, 9, 759.
94. Raymo, F.M.; Houk, K.N.; Stoddart, J.F. J. Org. Chem., 1998, 63, 6523.
95. Zhang, K.-C.; Liu, L.; Mu, T.-W.; Guo, Q.-X. Chem. Phys. Lett., 2001, 333, 195;
96. b) Kaminski, G.A.; Jorgensen, W.L. J. Chem. Soc., Perkin Trans. 2, 1999, 2365;
97. c) Castro, R.; Davidov, P.D.; Kumar, K.A.; Marchand, A.P.; Evanseck, J.D.; Kaifer, A.E. J. Phys. Org. Chem., 1997, 10, 369.
98. Lipton, M.A. Tetrahedron Lett., 1996, 37, 287.
99. Grabuleda, X.; Jaime, C. J. Org. Chem., 1998, 63, 9635.
100. Grabuleda, X.; Jaime, C.; Kollman, P.A. J. Comput Chem., 2000, 21, 901.
101. Grabuleda, X.; Ivanov, P.M.; Jaime, C. J. Org. Chem., 2003, 68, 1539.
102. Córdova, E.; Bissell, R.A; Spencer, N.; Ashton, P.R.; Stoddart, J.F.; Kaifer, A.E. J. Org. Chem., 1993, 58, 6550.
103. Kollman, P.A. Chem. Rev., 1993, 93, 2395.
104. Grabuleda, X.; Ivanov, P.; Jaime, C. J. Org. Chem., 2003, 68, 1539.
105. Hübner, G.M.; Gläser, J.; Seel. C.; Vogtle, F. Angew. Chem. Int. Ed., 1999, 38, 383.'
106. Lipkowitz, K.B.; Coner, B.; Peterson M.A.; Morreale A. J. Phys. Org. Chem., 1997, 10, 311.