Molecular recognition in an organic host-guest complex: CH⋯O and CH⋯π interactions completely control the crystal packing and the host-guest complexation

Bulletin of the Chemical Society of Japan

Volumn 80, Issue 3, 2007, Pages 484-490

  Radhakrishnan, Kokkuvayil Vasu ^a   Anas, Saithalavi ^a   Suresh, Eringathodi ^b   Koga, Nobuaki ^c   Suresh, Cherumuttathu Hariharan ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

^c NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL PACKING; CRYSTAL STRUCTURE ANALYSIS; MOLECULAR ELECTROSTATIC POTENTIAL ANALYSIS; ORGANIC HOST GUEST COMPLEX;

COMPLEXATION; CRYSTAL STRUCTURE; MATHEMATICAL MODELS; NITROGEN COMPOUNDS; OPTIMIZATION; SYNTHESIS (CHEMICAL);

MOLECULAR RECOGNITION;

ACETIC ACID ETHYL ESTER; AZAPOLYCYCLE DERIVATIVE; ORGANIC COMPOUND; POLYCYCLIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL REACTION; CRYSTAL STRUCTURE; ELECTRICITY; MOLECULAR RECOGNITION;

EID: 33947189047     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.80.484     Document Type: Article

References (73)

1. a) J. D. Dunitz, A. Gavezzotti, Angew. Chem., Int. Ed. 2005, 44, 1766.
2. b) G. R. Desiraju, Acc. Chem. Res. 2002, 35, 565.
3. c) A. Frontera, C. Garau, D. Quinonero, P. Ballester, A. Costa, P. M. Deya, Org. Lett. 2003, 5, 1135.
4. d) E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem., Int. Ed. 2003, 42, 1210.
5. e) M. Nishio, Tetrahedron 2005, 61, 6923.
6. f) C. A. Hunter, Angew. Chem., Int. Ed. 2004, 43, 5310.
7. a) G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University Press, New York, 1997.
8. b) G. R. Desiraju, T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press, Oxford, 1999.
9. c) M. Meot-Ner, Chem. Rev. 2005, 105, 213.
10. T. Steiner, Angew. Chem., Int. Ed. 2002, 41, 48.
11. a) K. Biradha, CrystEngComm 2003, 5, 374.
12. b) M. Nishio, CrystEngComm 2004, 6, 130.
13. c) W. Reckien, S. D. Peyerimhoff, J. Phys. Chem. A 2003, 107, 9634.
14. d) N. Schultheiss, C. L. Barnes, E. Bosch, Cryst. Growth Des. 2003, 3, 573.
15. e) L. R. Nassimbeni, Acc. Chem. Res. 2003, 36, 631.
16. f) V. Klusak, Z. Havlas, L. Rulisek, J. Vondrasek, A. Svatos, Chem. Biol. 2003, 10, 331.
17. g) R. J. Doerksen, C. Bin, D. H. Liu, G. N. Tew, W. F. DeGrado, M. L. Klein, Chem. Eur. J. 2004, 10, 5008.
18. h) S. Yohannan, S. Faham, D. Yang, D. Grosfeld, A. K. Chamberlain, J. U. Bowie, J. Am. Chem. Soc. 2004, 126, 2284.
19. i) V. Spiwok, P. Lipovova, T. Skalova, E. Buchtelova, J. Hasek, B. Kralova, Carbohydr. Res. 2004, 339, 2275.
20. Y. Umezawa, S. Tsuboyama, H. Takahashi, J. Uzawa, M. Nishio, Tetrahedron 1999, 55, 10047.
21. a) G. Bhattacharjya, G. Savitha, G. Ramanathan, CrystEngComm 2004, 6, 233.
22. b) S. Blanco, J. C. Lopez, A. Lesarri, W. Caminati, J. L. Alonso, ChemPhysChem 2004, 5, 1779.
23. c) R. K. Castellano, Curr. Org. Chem. 2004, 8, 845.
24. d) A. Cosp, I. Larrosa, J. M. Anglada, J. M. Bofill, P. Romea, F. Urpi, Org. Lett. 2003, 5, 2809.
25. e) V. Venkatesan, A. Fujii, N. Mikami, Chem. Phys. Lett. 2005, 409, 57.
26. f) C. Ramos, P. R. Winter, J. A. Stearns, T. S. Zwier, J. Phys. Chem. A 2003, 107, 10280.
27. g) V. Chandrasekhar, S. Nagendran, S. Bansal, A. W. Cordes, A. Vij, Organometallics 2002, 21, 3297.
28. h) H. Mansikkamäki, M. Nissinen, K. Rissanen, Angew. Chem., Int. Ed. 2004, 43, 1243.
29. a) H. Olsen, Angew. Chem., Int. Ed. 1982, 21, 383.
30. b) B.-C. Hong, A. K. Gupta, M.-F. Wu, J.-H. Liao, Tetrahedron Lett. 2004, 45, 1663.
31. For [2 + 2], see: a) K. Imafuku, K. Arai, Synthesis 1989, 501.
32. b) L. A. Paquette, J. A. Colapret, D. R. Andrews, J. Org. Chem. 1985, 50, 201.
33. For [4 + 2] see: c) M. Harre, P. Raddatz, R. Walenta, E. Winterfeldt, Angew. Chem., Int. Ed. 1982, 21, 480.
34. d) R. Gleiter, O. Borzyk, Angew. Chem., Int. Ed. 1995, 34, 1001.
35. For [2 + 4], see: e) Y. Himeda, H. Yamataka, I. Ueda, M. Hatanaka, J. Org. Chem. 1997, 62, 6529.
36. For [6 + 4], see: f) Y. N. Gupta, M. J. Doa, K. N. Houk, J. Am. Chem. Soc. 1982, 104, 7336.
37. g) Z.-I. Yoshida, M. Shibata, E. Ogino, T. Sugimoto, Angew. Chem., Int. Ed. 1985, 24, 60.
38. For [6 + 2] and [6 + 3], see: h) B.-C. Hong, Y. J. Shr, J. L. Wu, A. K. Gupta, K. Lin, Org. Lett. 2002, 4, 2249.
39. i) M. Suda, K. Hafner, Tetrahedron Lett. 1977, 18, 2453.
40. j) T. C. Wu, K. N. Houk, J. Am. Chem. Soc. 1985, 107, 5308.
41. k) B.-C. Hong, S. S. Sun, Y. C. Tsai, J. Org. Chem. 1997, 62, 7717.
42. l) J. Barluenga, S. Martinez, A. L. Suarez-Sobrino, M. Tomas, J. Am. Chem. Soc. 2001, 123, 11113.
43. m) K. V. Radhakrishnan, K. Syam Krishnan, M. M. Bhadbhade, G. V. Bhosekar, Tetrahedron Lett. 2005, 46, 4785, and references cited therein.
44. n) S. K. Krishnan, V. S. Sajisha, S. Anas, C. H. Suresh, M. M. Bhadbhade, G. V. Bhosekar, K. V. Radhakrishnan, Tetrahedron 2006, 62, 5952.
45. a) R. C. Cookson, S. S. H. Gilani, I. D. R. Stevens, Tetrahedron Lett. 1962, 3, 615.
46. b) R. C. Gupta, C. M. Raynor, R. J. Stoodley, A. M. Z. Slawin, D. J. Williams, J. Chem. Soc., Perkin Trans. 1 1988, 1773.
47. c) R. C. Gupta, D. S. Larsen, R. J. Stoodley, J. Chem. Soc., Perkin Trans. 1 1989, 739.
48. a) W. H. Pirkle, J. C. Stickler, Chem. Commun. 1967, 760.
49. b) W. Adam, A. Pastor, T. Wirth, Org. Lett. 2000, 2, 1295, and references cited therein.
50. a) SMART (V 5.628), SAINT (V 6.45a), XPREP, SHELXTL, Bruker AXS Inc., Madison, WI, 2004.
51. b) G. M. Sheldrick, SHELXL97, Program for Crystal Structure Refinement, University of Göttingen, Göttingen, Germany, 1997.
52. c) C. K. Johnson, ORTEP III, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, TN, 1976.
53. d) A. L. Spek, Acta Crystallogr., Sect. A 1990, 46, C34.
54. a) A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
55. b) A. D. Becke, Phys. Rev. A 1988, 38, 3098.
56. C. T. Lee, W. T. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
57. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Yengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford CT, 2004.
58. P. C. Hariharan, J. A. Pople, Mol. Phys. 1974, 27, 209.
59. J. J. P. Stewart, J. Comput. Chem. 1989, 10, 209.
60. a) P. Politzer, D. G. Truhlar, Chemical Applications of Atomic and Molecular Electrostatic Potentials, Plenum, New York, 1981.
61. b) S. R. Gadre, R. N. Shirsat, Electrostatics of Atoms and Molecules, Universities Press, Hyderabad, 2000.
62. c) F. S. Dukhovich, M. B. Darkhovskii, J. Mol. Recognit. 2003, 16, 191.
63. d) A. Boudon, J. Szymoniak, J. R. Chretien, Eur. J. Med. Chem. 1988, 23, 365.
64. e) C. K. Bagdassarian, V. L. Schramm, S. D. Schwartz, J. Am. Chem. Soc. 1996, 118, 8825.
65. f) P. Kovacic, L. P. G. Wakelin, Anti-Cancer Drug Des. 2001, 16, 175.
66. g) F. J. Luque, M. Orozco, P. K. Bhadane, S. R. Gadre, J. Phys. Chem. 1993, 97, 9380.
67. h) S. R. Gadre, K. Babu, A. P. Rendell, J. Phys. Chem. A 2000, 104, 8976.
68. i) C. H. Suresh, S. R. Gadre, J. Org. Chem. 1999, 64, 2505.
69. j) C. H. Suresh, N. Koga, S. R. Gadre, J. Org. Chem. 2001, 66, 6883.
70. k) C. H. Suresh, N. Koga, J. Am. Chem. Soc. 2002, 124, 1790.
71. l) P. Politzer, P. R. Laurence, K. Jayasuriya, Environ. Health Perspect. 1985, 61, 191.
72. m) J. S. Murray, S. Ranganathan, P. Politzer, J. Org. Chem. 1991, 56, 3734.
73. R. C. Smith, C. R. Bodner, M. J. Earl, N. C. Sears, N. E. Hill, L. M. Bishop, N. Sizemore, D. T. Hehemann, J. J. Bohn, J. D. Protasiewicz, J. Organomet. Chem. 2005, 690, 477.