CH/π Interaction in the Crystal Structure of Organic Compounds. A Database Study

Bulletin of the Chemical Society of Japan

Volumn 71, Issue 5, 1998, Pages 1207-1213

  Umezawa, Yoji ^a   Tsuboyama, Sei ^b   Honda, Kazumasa ^c   Uzawa, Jun ^b   Nishio, Motohiro ^d  

^a INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^c NATL INST OF MAT AND CHEM RES   (Japan)

^d CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001679930     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.71.1207     Document Type: Article

References (103)

1. a) M. Nishio and M. Hirota, Tetrahedron, 45, 7201 (1989);
2. b) M. Nishio, Y. Umezawa, M. Hirota, and Y. Takeuchi, Tetrahedron, 51, 8665 (1995);
3. c) M. Nishio, M. Hirota, and Y. Umezawa, "The CH/π Interaction. Evidence, Nature and Consequences," John Wiley & Sons, Inc., New York, in press (1998).
4. a) J. Uzawa, S. Zushi, Y. Kodama, Y. Fukuda, K. Nishihata, K. Umemura, M. Nishio, and M. Hirota, Bull. Chem. Soc. Jpn., 53, 3623 (1980);
5. b) H. Shimizu, T. Yonezawa, and T. Watanabe, J. Chem. Soc., Chem. Commun., 1996, 1659;
6. c) Y. Shimohigashi, I. Maeda, T. Nose, K. Ikesue, H. Sakamoto, T. Ogawa, Y. Ide, M. Kawahara, T. Nezu, Y. Terada, K. Kawano, and M. Ohno, J. Chew. Soc., Perkin Trans, 1, 1996, 2479;
7. d) J. A. Dickinson, P. W. Joireman, R. T. Kroemer, E. G. Robertson, and J. P. Simons, J. Chem. Soc., Faraday Trans., 1997, 1467.
8. a) M. Nishio, Kagaku no Ryoiki, 37, 243 (1983);
9. b) S. Araki, K. Sakakibara, M. Hirota, M. Nishio, S. Tsuzuki, and K. Tanabe, Tetrahedron Lett., 1991, 6587;
10. c) S. Araki, T. Seki, K. Sakakibara, M. Hirota, M. Nishio, and Y. Kodama, Tetrahedron: Asym., 4, 555 (1993).
11. a) G. D. Andreetti, F. Ugozzoli, R. Ungaro, and A. Pochini, "Inclusion Compounds," ed by J. L. Atwood, J. E. D. Davies, and D. D. McNicol, Oxford (1991), Vol. 4. p. 64. and references cited therein;
12. b) M. Perrin, F. Gharnati, D. Oehler, R. Perrin, and S. Lecocq, J. Inclusion Phenom., 14, 257 (1992);
13. c) G. Ferguson, J. F. Gallagher, and S. Pappalardo, J. Inclusion Phenom., 14, 349 (1992);
14. d) K. Kobayashi, Y. Asakawa, Y. Kalo, and Y. Aoyama, J. Am. Chem. Soc., 114, 10302 (1992);
15. e) P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, and D. J. Williams, J. Chem. Soc., Chem. Commun., 1994, 181.
16. a) F. G. Klärner, J. Benkhoff, R. Boese, U. Burkert, M. Kamieth, and U. Naatz, Angew. Chem., Int. Ed. Engl., 35, 1130 (1996);
17. b) K. Ochiai, Y. Mazaki, S. Nishikiori, K. Kobayashi, and S. Hayashi, J. Chem. Soc., Perkin Trans. 2, 1996, 1139;
18. c) S. Breidenbach, J. Harren, S. Neumann, M. Nieger, K. Rissanen, and F. Vögtle, J. Chem. Soc., Perkin Trans. 1, 1996, 2061;
19. d) H. Tomori, H. Yoshihara, and K. Ogura, Bull. Chem. Soc. Jpn., 69, 3581 (1996).
20. a) K. Miyamura, A. Mihara, T. Fujii, Y. Gohshi, and Y. Ishii, J. Am. Chem. Soc., 117, 2377 (1995);
21. b) A. Mori, K. Hirayama, N. Kato, A. Takeshita, and S. Ujiie, Chem. Lett., 1997, 509.
22. a) H. Okawa, Coord. Chem. Rev., 92, 1 (1988);
23. b) M. Nakamura, Inorg. Chim. Acta, 161, 73 (1989);
24. c) H. Imai and Y. Uemori, J. Chem. Soc., Perkin Trans. 2, 1994, 1793;
25. d) T. E. Müller, D. M. P. Mingos, and D. J. Williams, J. Chem, Soc., Chem. Commun., 1994, 1787;
26. e) K. Yamanari, T. Nozaki, A. Fuyuhiro, Y. Kushi, and S. Kaizaki, J. Chem, Soc., Dalton Trans., 1996, 2851.
27. a) T. Endo, M. M. Ito, Y. Yamada, H. Saito, K. Miyazawa, and M. Nishio, J. Chem. Soc., Chem. Commun., 1983, 1430;
28. b) Y. Sasaki, H. Kawaki, T. Takagi, T. Murakami, S. Fujii, and F. Masuda, Chem. Pharm. Bull., 38, 721 (1990);
29. c) Y. Abe, W. Qing, T. Shoji, S. Fukui, M. Suzuki, T. Kamiyama, M. Kobayashi, and H. Nishizawa, Chem. Pharm. Bull., 44, 1250 (1996).
30. a) T. Kawabata, A. Kuroda, K. Takasu, and K. Fuji, Tetrahedron Lett., 1996, 4153;
31. b) R. W. Quan, Z. Li, and E. N. Jacobsen, J. Am. Chem. Soc., 118, 8156 (1996);
32. c) M. Akazome, M. Noguchi, O. Tanaka, A. Sumikawa, T. Uchida, and K. Ogura, Tetrahedron, 53, 8315 (1997).
33. a) D. B. Amabilino, P. R. Ashton, J. F. Stoddart, S. Menzer, and D. J. Williams, J. Chem. Soc., Chem. Commun., 1994, 2475;
34. b) D. Armspach, P. R. Ashton, R. Ballardini, V. Balzuni, A. Godi, C. P. Moore, L. Prodi, N. Spencer, J. F. Stoddart, M. S. Tolley, T. J. Wear, and D. J. Williams, Chem. Eur. J., 1, 33 (1995);
35. c) M. Asakawa, W. Dehaen, G. L'abbé, S. Menzer, J. Nouwen, F. M. Raymo, J. F. Stoddart, and D. J. Williams, J. Org. Chem., 61, 9591 (1996).
36. Y. Umezawa and M. Nishio, Bioorg. Med. Chem., 6, 493 (1998).
37. a) M. Yun, C. Park, S. Kim, D. Nam, S. C. Kim, and D. H. Kim, J. Am. Chem. Soc., 114, 2281 (1992);
38. b) T. Tanaka, M. Hirama, K. Fujita, S. Imajo, and M. Ishiguro, J. Chem. Soc., Chem. Commun., 1993, 1205;
39. c) K. Jitsukawa, K. Iwai, H. Masuda, H. Ogoshi, and H. Einaga, Chem. Lett., 1994, 303;
40. d) P. Chakrabarti and U. Samanta, J. Mol. Biol., 251, 9 (1995).
41. a) N. Morisaki, H. Funabashi, R. Shimazawa, J. Furukawa, A. Kawaguchi, S. Okuda, and S. Iwasaki, Eur. J. Biochem., 211, 111 (1993);
42. b) I. Maeda, Y. Shimohigashi, K. Ikesue, T. Nose, Y. Ide, K. Kawano, and M. Ohno, J. Biochem., 119, 870 (1996);
43. c) T. Kawasaki, K. Saito, and H. Ohta, Chem. Lett., 1997, 351.
44. a) A. Doubleday, H. Higgs, T. Hummelink, B. G. Hummelink-Peters, O. Kennard, W. D. S. Motherwell, J. R. Rodgers, and D. G. Watson, Acta Crystallogr., Sect B., 35B, 2331 (1979);
45. b) F. H. Allen, J. E. Davies, J. J. Galloy, O. Johnson, O. Kennard, C. F. Macrae, E. M. Mitchell, G. F. Mitchell, J. M. Smith, and D. G. Watson, J. Chem. Inf. Comput. Sci., 31, 187 (1991).
46. a) T. Takagi, A. Tanaka, S. Matsuo, H. Maezaki, M. Tani, H. Fujiwara, and Y. Sasaki, J. Chem. Soc., Perkin Trans. 2, 1987, 1015;
47. b) B. W. Gung, Z. Zhu, and R. A. Fouch, J. Am. Chem. Soc., 117, 1783 (1995);
48. c) M.-F. Fan, Z. Lin, J. E. McGrady, and D. M. P. Mingos, J. Chem, Soc., Perkin Trans. 2, 1996, 563.
49. liy.
50. For X-ray data, the C-H bond distance was corrected to a standard value of 1.083 A in the QUEST program.
51. a) M. A. Viswamitra, R. Radhakrishnan, J. Bandekar, and G. R. Desiraju, J. Am. Chem. Soc., 115, 4868 (1993);
52. b) T. Steiner, M. Tamm, B. Lutz, and J. van der Maas, J. Chem. Soc., Chem. Commun., 1996, 1127.
53. a) Z. Yoshida and E. Osawa, J. Am. Chem. Soc., 87, 1467 (1965);
54. b) M. Oki, H. Iwamura, T. Onoda, and M. Iwamura, Tetrahedron. 24, 1905 (1968);
55. c) S. Ueji, K. Makatsu, H. Yoshioka, and K. Kinoshita, Tetrahedron Lett., 1982, 1173;
56. d) M. F. Perutz, Philos. Trans. R. Soc. London, Ser. A, 345, 105 (1993).
57. a) M. Oki and K. Mutai, Bull. Chem, Soc. Jpn., 33, 784 (1960);
58. b) M. Levitt and M. F. Perutz, J. Mol. Biol., 201, 751 (1988);
59. c) L. R. Hanton, C. A. Hunter, and D. H. Purvis, J. Chem. Soc., Chem. Commun., 1992, 1134.
60. a) D. J. Sutor, J. Chem. Soc., 1963, 1105;
61. b) A. Allerhand and P. von Rauge-Schleyer, J. Am. Chem. Soc., 85, 1715 (1963);
62. c) R. Taylor and O. Kennard, J. Am. Chem. Soc., 104, 5063 (1982);
63. d) G. R. Desiraju, Acc. Chem. Res., 24, 290 (1991).
64. liy>0.4 Å [Fig. 2(a)] are shown.
65. L. Pauling, "The Nature of the Chemical Bonds," Cornell Univ. Press, Ithaca, New York (1960), p. 260.
66. a) G. R. Desiraju, J. Chem. Soc., Chem. Commun., 1989, 179;
67. b) T. Steiner and W. Saenger, J. Am. Chem. Soc., 114, 10146 (1992).
68. pln shorter lhan 2.9 Å [Fig. 2(b)] are shown.
69. lix > -0.1 Å [Fig. 2(c)] are shown.
70. a) T. Steiner, J. Chem. Soc., Chem. Commun., 1995, 95;
71. b) T. Steiner, E. B. Starikov, A. M. Amado, and J. J. C. Teixeria-Dias, J. Chem. Soc., Perkin Trans. 2, 1995, 1321.
72. a) S. K. Burley and G. A. Petsko, Science, 229, 23 (1985);
73. b) J. Singh and J. M. Thornton, FEBS Lett., 191, 1 (1985);
74. c) S. K. Burley and G. A. Petsko, J. Am. Chem, Soc., 108, 7995 (1986);
75. d) S. K. Burley and G. A. Petsko, Adv. Protein Chem., 39, 125 (1988);
76. e) T. A. Hamor, W. B. Jennings, L. D. Proctor, M. S. Tolley, D. R. Boyd, and T. Mullan, J. Chem. Soc., Perkin Trans. 2, 1990, 25;
77. f) J. Singh and J. M. Thornton, J. Mol. Biol., 211, 595 (1990);
78. g) W. L. Jorgensen and D. L. Severance, J. Am. Chem. Soc., 112, 4768 (1990);
79. h) C. A. Hunter, J. Singh, and J. M. Thornton, J. Mol. Biol., 218, 837 (1991);
80. i) M. C. Grossel, A. K. Cheetham, D. A. O. Hope, and S. C. Westen, J. Org. Chem., 58, 6654 (1993).
81. Explanations based primarily on electrostatic interaction (positive CH versus negative π-doud) were proposed. The nature of this interaction has, however, remained as an open question. In our view, this phenomenon is better accommodated in the context of the CH/π interaction.
82. 1) are around 30°, irrespective of the type of compounds.
83. A. C. Hazell, R. G. Hazell, L. Norskov-Lauristsen, C. E. Briant, and D. W. Jones, Acta Crystallogr., Sect. C, 42C, 690 (1986).
84. G. E. Bacon and R. J. Jude, Z Kristallogr., 138, 19 (1973).
85. A. R. Al-Karaghouli and T. F. Koetzle, Acta Crystallogr., Sect. B. 318, 2461 (1975).
86. M. Perrin, F. Gharnati, D. Oehler, R. Perrin, and S. Lecocq, J. Inclusion Phenom., 14, 257 (1992).
87. a) N. Nakagawa, Nippon Kagaku Zasshi, 82, 141 (1961);
88. b) M. Karatsu, H. Suezawa, K. Abe, M. Hirota, and M. Nishio, Bull. Chem. Soc. Jpn., 59, 3529 (1986);
89. c) S. K. Chowdhury, V. S. Joshi, A. G. Samuel, V. G. Puranik, S. S. Tavale, and A. Sarkar, Organometallics. 13, 4092 (1994).
90. a) Y. Nakai, K. Inoue, G. Yamamoto, and M. Oki, Bull. Chem. Soc. Jpn., 62, 2923 (1989);
91. b) H. Suezawa, A. Mori, M. Sato, R. Ehama, I. Akai, K. Sakakibara, M. Hirota, M. Nishio, and Y. Kodama, J. Phys. Org. Chem., 6, 399 (1993);
92. c) S. Paliwal, S. Geib, and C. S. Wilcox, J. Am. Chem. Soc., 116, 4497 (1994);
93. d) H. Sugimoto, T. Aida, and S. Inoue, J. Chem. Soc., Chem. Commun., 1995, 1411.
94. a) K. Kobayashi, Y. Asakawa, and Y. Aoyama, Supramol. Chem., 2, 133 (1993);
95. b) R. Ehama, A. Yokoo, M. Tsushima, T. Yuzuri, H. Suezawa, and M. Hirota, Bull. Chem. Soc. Jpn., 66, 814 (1993);
96. c) T. Fujimoto, R. Yanagihara, K. Kobayashi, and Y. Aoyama, Bull. Chem. Soc. Jpn., 68, 2113 (1995).
97. K. Abe, M. Hirota, and K. Morokuma, Bull Chem. Soc. Jpn., 58, 2713 (1985).
98. a) H. M. Colquhoun, J. F. Stoddart, and D. J. Williams, Angew. Chem., Int. Ed. Engl., 25, 487 (1986);
99. b) R. Hunter, R. H. Haueisen, and A. Irving, Angew. Chem., Int. Ed. Engl., 33, 566 (1994);
100. c) H.-B. Bürgi, K. K. Baldridge, K. Hardcastle, N. L. Frank, P. Ganzel, J. S. Siegel, and J. Ziller, Angew. Chem., Int. Ed. Engl., 34, 1454 (1995);
101. d) T. Steiner, M. Tamm, B. Lutz, and J. van der Maas, J. Chem. Soc., Chem. Commun., 1996, 1127;
102. e) N. L. Frank, K. K. Baldridge, P. Gantzel, and J. S. Siegel, Tetrahedron Lett., 1995, 4389;
103. g) N. Nagel, C. Näther, and H. Bock, Acta Crystallogr., Sect. C, 53C, 79 (1997).