Tri- and tetraurea piperazine cyclophanes: Synthesis and complexation studies of preorganized and folded receptor molecules

Chemistry - A European Journal

Volumn 16, Issue 48, 2010, Pages 14554-14564

  Raatikainen, Kari ^a   Beyeh, N Kodiah ^a   Rissanen, Kari ^a  

^a UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

cyclophanes; host guest systems; receptors; supramolecular chemistry; urea; X ray diffraction

Indexed keywords

ACIDIC CONDITIONS; COMPLEXATION PROPERTIES; CYCLOPHANES; DIISOPROPYL ETHER; FUNCTIONALIZED; GASPHASE; HOST-GUEST SYSTEM; INTRAMOLECULAR HYDROGEN; INTRAMOLECULAR HYDROGEN BOND; ION PAIRS; ION-PAIR COMPLEXES; LARGE SIZES; LIPOPHILIC CAVITY; N -PHENYLUREA; PHENYL ISOCYANATES; QUANTITATIVE YIELDS; RECEPTORS; RECOGNITION SITE; SINGLE CRYSTAL X-RAY DIFFRACTION; UREA MOIETIES; VARIABLE-TEMPERATURE NMR;

BINDING SITES; CONFORMATIONS; DIFFRACTION; ETHERS; HYDROGEN; MACROMOLECULES; METABOLISM; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POTASSIUM IODIDE; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS (CHEMICAL); THERMOANALYSIS; THERMOMECHANICAL PULPING PROCESS; UREA; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS; X RAYS;

HYDROGEN BONDS;

EID: 78651234055     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001695     Document Type: Article

References (76)

1. D. J. Cram, Science 1988, 240, 760.
2. J-;M. Lehn, Supramolecular chemistry-Scope and Perspectives, Wiley-VCH, Weinheim, 1995.
3. C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017
4. C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 2495.
5. J.-M. Lehn, Acc. Chem. Res. 1978, 11, 49
6. J.-M. Lehn, Pure Appl. Chem. 1978, 50, 871.
7. D. Coquière, S. LeGac, U. Darbost, O. Seneque, I. Jabin, O. Reinaud, Org. Biomol. Chem. 2009, 7, 2485
8. C.-H. Lee, H. Miyaji, D.-W. Yoon, J. L. Sessler, Chem. Commun. 2008, 24
9. V. Arora, H. M. Chawla, S. P. Singh, ARKIVOC 2007, 172.
10. M. C. Etter, T. W. Panunto, J. Am. Chem. Soc. 1988, 110, 5896.
11. M. Menand, I. Jabin, Org. Lett. 2009, 11, 673
12. J. N. Babu, V. Bhalla, M. Kumar, R. K. Puri, R. K. Mahajan, New J. Chem. 2009, 33, 675
13. J. Babu, B. Nagendra; K. Vandana; M. R. K. Manoj; R. K. Puri, Tetrahedron Lett. 2008, 49, 2772
14. K. Vandana; M. R. K. Manoj; R. K. Puri, Tetrahedron Lett. 2008, 49, 2772
15. J. Budka, P. Lhotak, V. Michlova, I Stibor, Tetrahedron Lett. 2001, 42, 1583
16. J. Scheerder, R. H. Vreekamp, J. F. J. Engbersen, W. Verboom, J. P. M. vanDuynhoven, D. N. Reinhoudt, J. Org. Chem. 1996, 61, 3476
17. J. Scheerder, J. P. M. vanDuynhoven, J. F. J. Engbersen, D. N. Reinhouldt, Angew. Chem. 1996, 109, 1172
18. Angew. Chem. Int. Ed. Engl. 1996, 35, 1090
19. J. Scheerder, M. Fochi, J. F. J. Engbersen, D. N. Reinhoudt, J. Org. Chem. 1994, 59, 7815.
20. E. Métay, M. C. Duclos, S. Pellet-Rostaing, M. Lemaire, J. Schulz, R. Kannappan, C. Bucher, E. Saint-Aman, C. Chaix, Eur. J. Org. Chem. 2008, 4304
21. E. Métay, M. C. Duclos, S. Pellet-Rostaing, M. Lemaire, J. Schulz, R. Kannappan, C. Bucher, E. Saint-Aman, C. Chaix, Eur. J. Org. Chem. 2008, 4304
22. B. Schazmann, N. Alhashimy, D. Diamond, J. Am. Chem. Soc. 2006, 128, 8607
23. A. J. Evans, S. E. Matthews, A. R. Cowley, P. D. Beer, Dalton Trans. 2003, 4644.
24. T. Haino, M. Nakamura, N. Kato, M. Hiraoka, Y. Fukazawa, Tetrahedron Lett. 2004, 45, 2281.
25. A. Arduini, E. Brindani, G. Giorgi, A. Pochini, A. Secchi, Tetrahedron 2003, 59, 7587.
26. F. P. Ballistreri, A. Notti, S. Pappalardo, M. F. Parisi, P. I. Pisagatti, Org. Lett. 2003, 5, 1071
27. A. V. Yakovenko, V. I. Boyko, V. L. Kalchenko, L. Baldini, A. Casnati, F. Sansone, R. Ungaro, J. Org. Chem. 2007, 72, 3223.
28. M. Hamon, M. Menand, S. LeGac, M. Luhmer, V. Dalla, I Jabin, J. Org. Chem. 2008, 73, 7067
29. N. Pelizzi, A. Casnati, A. Friggeri, R. Ungaro, J. Chem. Soc. Perkin Trans. 2 1998, 1307.
30. D. C. Gutsche, Acc. Chem. Res. 1983, 16, 161
31. P. Timmerman, W. Verboom, D. Reinhoudt, Tetrahedron 1996, 52, 2663.
32. D. M. Rudkevich, G. Hilmersson, J. Rebek Jr., J. Am. Chem. Soc. 1998, 120, 12216
33. A. Shivanyuk, K. Rissanen, S. K. Korner, D. M. Rudkevich, J. Rebek, Jr., Helv. Chim. Acta 2000, 83, 1778
34. A. R. Renslo, F. C. Tucci, D. M. Rudkevich, J. Rebek, Jr., J. Am. Chem. Soc. 2000, 122, 4573
35. R. J. Hooley, J. Rebek, Jr., J. Am. Chem. Soc. 2005, 127, 11904
36. A. Lledõ, J. Rebek, Jr., Chem. Commun. 2010, 46, 1637.
37. D. Ajami, J. Rebek, Jr., J. Org. Chem. 2009, 74, 6584
38. L. R. MacGillivray, J. L. Atwood, Nature 1997, 389, 469
39. L. Avram, Y. Cohen, J. Am. Chem. Soc. 2004, 126, 11556
40. K. Kobayashi, K. Ishii, S. Sakamoto, T. Shirasaka, K. Yamaguchi, J. Am. Chem. Soc. 2003, 125, 10615
41. F. Fochi, P. Jacopozzi, E. Wegelius, K. Rissanen, P. Cozzini, E. Marastoni, E. Fisicaro, P. Manini, R. Fokkens, E. Dalcanale, J. Am. Chem. Soc. 2001, 123, 7539
42. G. V. Oshovsky, D. N. Reinhoudt, W. Verboom, J. Am. Chem. Soc. 2006, 128, 5270.
43. K. Rissanen, K. J. Huuskonen, A. Koskinen, J. Chem. Soc. Chem. Commun. 1993, 771
44. K. Rissanen, J. Breitenbach, J. Huuskonen, J. Chem. Soc. Chem. Commun. 1994, 1265
45. J. Huuskonen, J. Schulz, K. Rissanen, Liebigs Ann. 1995, 1515
46. J. Huuskonen, J. Schulz, E. Kolehmainen, K. Rissanen, Chem. Ber. 1994, 127, 2267
47. J. Huuskonen, K. Rissanen, Liebigs Ann. 1995, 1611.
48. R. Gleiter, K. Hovermann, F. Rominger, T. Oeser, Eur. J. Org. Chem. 2001, 725
49. K. E. Krakowiak, J. S. Bradshaw, W. Jiang, N. K. Dalley, G. Wu, R. M. Izatt, J. Org. Chem. 1991, 56, 2675.
50. K. Raatikainen, J. Huuskonen, E. Kolehmainen, K. Rissanen, Chem. Eur. J. 2008, 14, 3297.
51. M. Przybylski, M. O. Glocker, Angew. Chem. 1996, 108, 878
52. Angew. Chem. Int. Ed. Engl. 1996, 35, 806
53. J. S. Brodbelt, Int. J. Mass Spectrom. 2000, 200, 57
54. C. A. Schalley, Int. J. Mass Spectrom. 2000, 194, 11
55. C. B. Lebrilla, Acc. Chem. Res. 2001, 34, 653
56. C. A. Schalley, Mass Spectrom. Rev. 2001, 20, 253.
57. SPARTAN 08, Wavefunction Inc., 18401 Von Karman Ave, Suite 370, Irvine
58. a) MMFF.
59. b) DFT, B3LYP, HF 6-31G.
60. K. Raatikainen, K. Rissanen, Cryst. Growth Des. 2010, 10, 3638.
61. N. L Allinger, J. G. D. Carpenter, F. M. Karkowski, J. Am. Chem. Soc. 1965, 87, 1232.
62. S. Mukhopadhyay, D. Mandal, P. B. Chatterjee, C. Desplanches, J.-P. Sutter, R. J. Butcher, M. Chaudhury, Inorg. Chem. 2004, 43, 8501
63. K. Kubono, K. Yokoi, Acta Crystallogr. Sect. A 2007, 63, 535
64. M. Kuppayee, D. Kumaran, M. N. Ponnuswamy, M. Kandaswamy, M. V. Jayanthi, K. Chinnakali, H.-K. Fun, Acta Crystallogr. Sect. A 1999, 55, 2147
65. K. Kubono, Y. Tsuno, K. Tani, K. Yokoi, Acta Crystallogr. Sect. A 2008, 64, o 2309
66. S. Mohanty, D. Suresh, M. S. Balakrishna, J. T. Mague, Tetrahedron 2008, 64, 240
67. R. Thirumurugan, S. S. S. Raj, G. Shanmugam, H.-K. Fun, K. Chinnakali, S. Chantrapromma, M. Marappan, M. Kandaswamy, Acta Crystallogr. Sect. A 1998, 54, 780
68. S. Loukiala, J. Ratilainen, J. Valkonen, K. Rissanen, Acta Chem.Scand. 1997, 51, 1162.
69. A. L. Spek, J. Appl. Crystallogr. 2003, 36, 7.
70. S. Mecozzi, J. Rebek, Jr., Chem. Eur. J. 1998, 4, 1016.
71. CCDC-780772, -780773, -780774, -780775 and -780772 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
72. COLLECT, R.W. Hooft, Nonius BV, Delft (The Netherlands), 1998.
73. Z. Otwinowski W. Minor, Methods Enzymol. 1997, 276, 307.
74. A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori R. Spagna, J. Appl. Crystallogr. 1999, 32, 115.
75. L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837.
76. G.M. Sheldrick, University of Göttingen (Germany), 1998.