4-tritylbenzoic acid. A molecular scaffold for wheel-and-axle host-guest inclusion compounds with a supramolecular axis

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 6, 2000, Pages 1223-1232

  Jetti, Ram K R ^a   Xue, Feng ^b   Mak, Thomas C W ^b   Nangia, Ashwini ^a  

^a UNIVERSITY OF HYDERABAD   (India)

^b CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTALLIZATION; DIMERS; SOLVENTS; STOICHIOMETRY; STRUCTURE (COMPOSITION); X RAY DIFFRACTION ANALYSIS;

CLATHRATE; ISOMORPHOUS STRUCTURES; TRIPHENYLMETHYL GROUPS; TRITYLBENZOIC ACID;

ORGANIC COMPOUNDS;

EID: 0034211771     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a909827e     Document Type: Article

References (77)

1. (a) E. Weber, in Kirk-Othmer Encyclopedia of Chemical Technology, 4th edn., ed. J. I. Kroschwitz, John Wiley, New York, 1995, vol. 14, pp. 122-154
2. (b) E. Weber, Comprehensive Supramolecular Chemistry, eds. D. D. MacNicol, F. Toda and. R. Bishop, Pergamon, Oxford, 1996, vol. 6
3. (c) R. Bishop, Chem. Soc. Rev., 1996, 25, 311
4. (d) Y. Aoyama, Top. Curr. Chem., 1998, 198, 131
5. (e) O. M Yaghi, H. Li, C. Davis, D. Richardson and T. L. Groy, Acc. Chem. Res., 1998, 31, 474
6. (f) L. R. MacGillivray and J. L. Atwood, Angew. Chem., Int. Ed., 1999, 38, 1018.
7. (a) M. Simard, D. Su and J. D. Wuest, J. Am. Chem. Soc., 1991, 113, 4696
8. (b) K. Endo, T. Sawaki, M. Koyanagi, K. Kobayashi, H. Masuda and Y. Aoyama, J. Am. Chem. Soc., 1995, 117, 8341
9. (c) M. Sugahara, K. Sada and M. Miyata, Chem. Commun., 1999, 293
10. (d) D. Hashizume and Y. Ohashi, J. Chem. Soc., Perkin Trans. 2, 1999, 1689.
11. (a) A. T. Ung, D. Gizachew, R. Bishop, M. L. Scudder, I. G. Dance and D. C. Craig, J. Am. Chem. Soc., 1995, 117, 8745
12. (b) K. Endo, T. Ezuhara, M. Koyanagi, H. Masuda and Y. Aoyama, J. Am. Chem. Soc., 1997, 119, 499
13. (c) M. R. Caira, A. Horne, L. R. Nassimbeni and F. Toda, J. Chem. Soc., Perkin Trans. 2, 1997, 1717
14. (d) K. Biradha, D. Dennis, V. A. MacKinnon, C. V. Krishnamohan Sharma and M. J. Zaworotko, J. Am. Chem. Soc., 1998, 120, 11894
15. (e) R. Thaimattam, D. S. Reddy, F. Xue, T. C. W. Mak, A. Nangia and G. R. Desiraju, J. Chem. Soc., Perkin Trans. 2, 1998, 1783.
16. S. R. Batten and R. Robson, Angew. Chem., Int. Ed., 1998, 37, 1460.
17. G. R. Desiraju, Angew. Chem., Int. Ed. Engl., 1995, 34, 2311.
18. G. A. Jeffrey and W. Saenger, Hydrogen Bonding in Biological Structures, Springer-Verlag, Berlin, 1991
19. G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University Press, Oxford, 1997.
20. G. R. Desiraju and T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press, Oxford, 1999.
21. A. T. Ung, R. Bishop, D. C. Craig, I. G. Dance and M. L. Scudder, Tetrahedron Lett., 1993, 49, 639.
22. E. Weber, T. Hens, O. Gallardo, and I. Csöregh, J. Chem. Soc., Perkin Trans. 2, 1996, 737.
23. B. Ibragimov, K. Beketov and K. Makhkamov and E. Weber, J. Chem. Soc., Perkin Trans. 2, 1997, 1349
24. K. Beketov, E. Weber, J. Seidel K. Köhnke, K. Makhkamov and B. Ibragimov, Chem. Commun., 1999, 91.
25. F. Toda and T. Tanaka, Tetrahedron Lett., 1988, 29, 551
26. E. Weber and C. Wimmer, Chirality, 1993, 2, 123.
27. L. R. MacGillivray and J. L. Atwood, J. Am. Chem. Soc., 1997, 119, 6931
28. G. W. Orr, L. J. Barbour and J. L. Atwood, Science, 1999, 285, 1049
29. G. Ferguson, C. Glidewell, A. J. Lough, G. D. McManus and P. R. Meehan, J. Mater. Chem., 1998, 2, 2339.
30. C. B. Aakeröy, A. M. Beatty and D. S. Leinen, Angew. Chem., Int. Ed., 1999, 38, 1815.
31. J. A. Swift, A. M. Pivovar, A. M. Reynolds and M. D. Ward, J. Am. Chem. Soc., 1998, 120, 5887
32. C. C. Evans, L. Sukarto and M. D. Ward, J. Am. Chem. Soc., 1999, 120, 5887
33. K. Sada, K. Yoshikawa and M. Miyata, Chem. Commun., 1998, 1763.
34. E. Weber, Comprehensive Supramolecular Chemistry, eds. D. D. MacNicol, F. Toda and R. Bishop, Pergamon, Oxford, 1996, vol. 6; pp. 14 and 15; 310-313; 467-470; 602-605.
35. (a) N. Hayashi, Y. Mazaki and K. Kobayashi, J. Chem. Soc., Chem. Commun., 1994, 2351
36. (b) H. Hart, L.-T. Lin and D. L. Ward, J. Am. Chem. Soc., 1984, 106, 4043
37. (c) F. Toda and K. Akagi, Tetrahedron Lett., 1968, 3695
38. (d) M. R. Caira, L. R. Nassimbeni, F. Toda and D. Vujovic, J. Chem. Soc., Perkin Trans. 2, 1999, 2681.
39. T. Minami, K. Nishimura I. Hirao, H. Suganuma and T. Agawa, J. Org. Chem., 1982, 47, 2360.
40. M. Grimm, B. Kriste and H. Kurreck, Angew. Chem., Int. Ed. Engl., 1986, 25, 1097
41. B. F. Hoskins and R. Robson, J. Am. Chem. Soc., 1990, 112, 1546.
42. P. R. Ashton, A. N. Collins, M. C. T. Fyfe, S. Menzer, J. F. Stoddart and D. J. Williams, Angew. Chem., Int. Ed. Engl., 1997, 36, 735.
43. (a) R. K. R. Jetti, S. S. Kuduva, D. S. Reddy, F. Xue, T. C. W. Mak, A. Nangia and G. R. Desiraju, Tetrahedron Lett., 1998, 39, 913
44. (b) A. Anthony, G. R. Desiraju, R. K. R. Jetti, S. S. Kuduva, N. N. L. Madhavi, A. Nangia, R. Thaimattam and V. R. Thalladi, Cryst. Eng., 1998, 1, 1.
45. I. Dance and M. Scudder, Chem. Eur. J., 1996, 2, 481.
46. T. Imakubo, T. Matuyama, H. Sawa and K. Kobayashi, Chem. Commun., 1998, 2021
47. A. J. Matzger, M. Shim and K. P. C. Vollhardt, Chem. Commun., 1999, 1871
48. K. K. Makhkamov, B. T. Ibragimov, E. Weber and K. M. Beketov, J. Phys. Org. Chem., 1999, 12, 157.
49. R. K. R. Jetti, H.-C. Weiss, V. R. Thalladi, R. Boese, A. Nangia and G. R. Desiraju, Acta Crystallogr., Sect. C, 1999, 55, 1530.
50. F. H. Allen, W. D. S. Motherwell, P. R. Raithby, G. P. Shields and R. Taylor, New J. Chem., 1999, 35.
51. A. Gavezzotti and G. Fillipini, J. Phys. Chem., 1994, 98, 4831
52. A. T. Hagler, P. Dauber and S. Lifson, J. Am. Chem. Soc., 1979, 101, 5131.
53. (a) G. R. Desiraju and A. Gavezzotti, J. Chem. Soc., Chem. Commun., 1989, 621
54. (b) C. A. Hunter, Chem. Soc. Rev., 1994, 23, 101
55. (c) I. Dance and M. Scudder, New J. Chem., 1998, 481.
56. G. R. Desiraju, Curr. Opinion Solid State Mater. Sci., 1997, 2, 451
57. H.-B. Bürgi, J. Hulliger and P. J. Langley, Curr. Opinion Solid State Mater. Sci., 1998, 3, 425
58. P. J. Langley and J. Hulliger, Chem. Soc. Rev., 1999, 28, 279.
59. P. Brunet, M. Simard and J. D. Wuest, J. Am. Chem. Soc., 1997, 119, 2737.
60. R. K. R. Jetti, F. Xue, T. C. W. Mak and A. Nangia, Cryst. Eng., 1999, 2, 215.
61. A. Nangia and G. R. Desiraju, Chem. Commun., 1999, 605.
62. 2, Molecular Simulations Inc., San Diego (USA) and Cambridge (UK).
63. S. A. Talipov, B. T. Ibragimov, G. N. Tischenko and T. F. Aripov, Kristallografiya, 1989, 34, 327 (Chem. Abstr., 1989, 110, 223061m).
64. E. Weber, N. Dörphinghaus and Csöregh, J. Chem. Soc., Perkin Trans. 2, 1990, 2167.
65. B. Kahr, and R. L. Carter, Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. A, 1992, 219, 79.
66. A. D. U. Hardy, D. D. MacNicol and D. R. Wilson, J. Chem. Soc., Perkin Trans. 2, 1979, 1011
67. A. S. Jessiman, D. D. MacNicol, P. R. Mallinson and I. Vallance, J. Chem. Soc., Chem. Commun., 1990 1619
68. D. D. MacNicol and G. A. Downing, Comprehensive Supramolecular Chemistry, eds. D. D. MacNicol, F. Toda and R. Bishop, Pergamon, Oxford, 1996, vol. 6, pp. 421-464.
69. V. S. S. Kumar, S. S. Kuduva and G. R. Desiraju, J. Chem. Soc., Perkin Trans. 2, 1999, 1069.
70. R. A. Sparks, in Crystallographic Computing Techniques, ed. F. R. Ahmed, Munksgaard, Copenhagen, 1976, p. 452.
71. Bruker SMART 5.0 and SAINT 4.0 for Windows NT: Area Detector Control and Integration Software, Bruker Analytical X-ray Instruments Inc., Madison, WI, 1998.
72. G. Kopfmann and R. Huber, Acta Crystallogr., Sect. A, 1968, 24, 348.
73. G. M. Sheldrick, SADABS: Program for Empirical Absorption Correction of Area Detector Data, University of Godie;ttingen, 1996.
74. G. M. Sheldrick, SHELXS 86, Acta Crystallogr., Sect. A, 46, 467, 1990
75. G. M. Sheldrick, SHELXL 93: A Program for the Refinement of Single Crystal Diffraction Data, University of Göttingen, 1993
76. G. M. Sheldrick, SHELXS 97: Program for the Solution of Crystal Structures, University of Göttingen, 1997
77. G. M. Sheldrick, SHELXL 97: Program for the Refinement of Crystal Structures, University of Göttingen, 1997.