1,3-Diindolylureas and 1,3-diindolylthioureas: Anion complexation studies in solution and the solid state

Chemistry - A European Journal

Volumn 14, Issue 33, 2008, Pages 10236-10243

  Caltagirone, Claudia ^a   Hiscock, Jennifer R ^a   Hursthouse, Michael B ^a   Light, Mark E ^a   Gale, Philip A ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

Anions; Indoles; Phosphate; Structure elucidation; Ureas

Indexed keywords

ANION COMPLEXATION; ANIONS; COORDINATION SPHERES; DIHYDROGEN PHOSPHATES; HIGH AFFINITIES; INDOLES; NEUTRAL RECEPTORS; PLANAR CONFORMATIONS; SOLID STATES; STRUCTURE ELUCIDATION;

DIMETHYL SULFOXIDE; HYDROGEN; HYDROGEN BONDS; IONS; NEGATIVE IONS; THIOUREAS; UREA;

SOLID SOLUTIONS;

EID: 56349130820     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801639     Document Type: Article

References (71)

1. a) P. A. Gale, S. E. García-Garrido, J. Garric, Chem. Soc. Rev. 2008, 37, 151-190;
2. b) P. Prados, R. Quesada, Supramol. Chem. 2008, 20, 201-216;
3. c) G. W. Bates, P. A. Gale; M. E. Light, CrystEngComm 2006, 8, 300-302,
4. Struct Bonding 2008, 129, 1-44;
5. d) J. L. Sessler, P. A. Gale, W. S. Cho, Anion Receptor Chemistry, Monographs in Supramolecular Chemistry (Ed.: J. F. Stoddart) Royal Society of Chemistry, Cambridge, 2006;
6. e) P. A. Gale, R. Quesada, Coord. Chem. Rev. 2006, 250, 3291-3244;
7. f) P. A. Gale, Acc. Chem. Res. 2006, 39, 465-475;
8. g) K. Bowman-James, Acc. Chem. Res. 2005, 38, 671-678;
9. h) P. A. Gale, Chem. Commun. 2005, 3761-3772;
10. i) P. A. Gale, Coord Chem. Rev. 2003, 240, 191-221;
11. j) P. D. Beer, P. A. Gale, Angew. Chem. 2001, 113, 502-532;
12. Angew. Chem. Int. Ed. 2001, 40, 486-516;
13. k) P. A. Gale, Coord. Chem. Rev. 2001, 213, 79-128;
14. l) F. P. Schmidtchen, M. Berger, Chem. Rev. 1997, 97, 1609-1646.
15. For an overview see: a) P. A. Gale, Chem. Commun. 2008, DOI:10.1039/B809508F;
16. for key papers see: b) P. Piatek, V. M. Lynch, J. L. Sessler, J. Am. Chem. Soc. 2004, 126, 16073-16076;
17. c) M. J. Chmielewski, M. Charon, J. Jurczak, Org. Lett. 2004, 6, 3501-3504;
18. d) J. O. Yu, C. S. Browning, D. H. Farrar, Chem. Commun. 2008, 1020-1022;
19. e) F. M. Pfeffer, K. F. Lim, K. J. Sedgwick, Org. Biomol. Chem. 2007, 5, 1795-1799;
20. f) K.-J. Chang, D. Moon, M. S. Lan, K. S. Jeong, Angew. Chem. 2005, 117, 8140-8143;
21. Angew. Chem. Int. Ed. 2005, 44, 7926-7929;
22. g) J.-m. Suk, M. K. Chae, N.-K. Kim, U.-I Kim, K.-S. Jeong, Pure Appl. Chem. 2008, 80, 599-608;
23. h) D. Curiel, A. Cowley, P. D. Beer, Chem. Commun. 2005, 236-238;
24. i) M. J. Chmielewski, L. Zhao, A. Brown, D. Curiel, M. R. Sambrook, A. L. Thompson, S. M., Santos, V. Felix, J. J. Davis, P. D. Beer, Chem. Commun. 2008, 3154-3156.
25. F. G. Bordwell, G. E. Drucker, H. E. Fried, J. Org. Chem. 1981, 46, 632-635.
26. K. H. G. Verschueren, F. Seljee, H. J. Rozeboom, K. H. Kalk, B. W. Dijkstra, Nature 1993, 565, 693-698.
27. J. J. He, F. A. Quiocho, Science 1991, 251, 1479-1481.
28. a) P. A. Gale, M. B. Hursthouse, M. E. Light, J. L. Sessler, C. N. Warriner, R. Zimmerman, Tetrahedron Lett. 2001, 42, 6759-6762;
29. b) P. A. Gale, S. Camiolo, C. P. Chapman, M. E. Light, M. B. Hurst-house, Tetrahedron Lett. 2001, 42, 5095-5097;
30. c) P. A. Gale, M. E. Light, B. McNally, K. Navakhun, K. E. Sliwinski, B. D. Smith, Chem. Commun. 2005, 3773-3775;
31. d) S. J. Brooks, P. A. Gale, M. E. Light, Chem. Commun. 2005, 4696-4698;
32. e) I. El Drubi Vega, P. A. Gale, M. E. Light; S. J. Loeb, Chem. Commun. 2005, 4913-4915;
33. S. J. Loeb, Chem. Commun. 2005, 4913-4915;
34. f) L. S. Evans, P. A. Gale, M. E. Light; R. Quesada, Chem. Commun. 2006, 965-967;
35. R. Quesada, Chem. Commun. 2006, 965-967;
36. g) G. W. Bates, P. A. Gale; M. E. Light, CrystEngComm 2006, 8, 300-302;
37. h) S. J. Brooks, P. A. Gale, M. E. Light, Chem. Commun. 2006, 4344-4346;
38. S. E. García-Garrido, C. Caltagirone, M. E. Light, P. A. Gale, Chem. Commun. 2007, 1450-1452;
39. j) C Caltagirone, G. W. Bates, P. A. Gale, M. E. Light, Chem Commun. 2008, 61-63.
40. G. W. Bates, P. A. Gale, M. E. Light, Chem. Commun. 2007, 2121-2123.
41. C. Caltagirone, P. A. Gale, J. R. Hiscock, M. B. Hursthouse, M. E. Light, G. J. Tizzard, Supramolecular Chem. 2009, in press.
42. C. W. Bates, Triyanti, M. E. Light, M. Albrecht, P. A. Gale, J. Org. Chem. 2007, 72, 8921-8927.
43. Aspects of this work have been communicated see: C Caltagirone, P. A. Gale, J. R. Hiscock, S. J. Brooks, M. B. Hursthouse, M. E. Light, Chem. Commun. 2008, 3007-3009.
44. M. J. Hynes, J. Chem. Soc. Dalton Trans. 1993, 311-312.
45. P. Job, Justus Liebigs Ann. Chem. 1928, 9, 113-203.
46. D. E. Gross, F. P. Schmidtchen, W. Antonius, P. A. Gale, V. M. Lynch, J. L. Sessler, Chem. Ew. J. 2008, 14, 7822-7827.
47. For examples of carbonate bound to macrocyclic hydrogen donor receptors,9 see: a) S. J. Brooks, S. E. García-Garrido, M. E. Light, P. A. Cole, P. A. Gale, Chem. Eur. J. 2007, 13, 3320-3329;
48. b) R. Custelcean, L. H. Delmau, B. A. Moyer, J. L. Sessler, W.-S. Cho, D. Gross, G. W. Bates, S. J. Brooks, M. E. Light, P. A. Gale, Angew. Chem. 2005, 117, 2593-2598;
49. Angew. Chem. Int. Ed. 2005, 44, 2537-2542.
50. a) R. Custelcean, P. Remy, P. V. Bonnesen, D.-e. Jiang, B. A. Moyer, Angew. Chem. 2008, 120, 1892-1896;
51. Angew. Chem. Int. Ed. 2008, 47, 1866-1870;
52. see also b) B. Wu, J. Liang, J. Yang, C. Jia, X-J. Yang, H. Zhang, N. Tang, C. Janiak, Chem. Commun. 2008, 1762-1764.
53. For other crystallographically characterised sulfate complexes see: c) S. O. Kang, M. A. Hossain, D. Powell, K. Bowman-James, Chem. Commun. 2005, 328-330;
54. d) R. Custelcean, V. Sellin, B. A. Moyer, Chem. Commun. 2007, 1541-1543;
55. e) C. R. Bondy, P. A. Gale, S. J. Loeb, J. Am. Chem. Soc. 2004, 126, 5030-5031.
56. H. Luecke, F. A. Quiocho, Nature 1990, 347, 402-406.
57. E. A. Katayev, J. L. Sessler, V. N. Khrustalev, Y. A. Ustynyuk, J. Org. Chem. 2007, 72, 7244-7252.
58. S. J. Brooks, P. R. Edwards, P. A. Gale, M. E. Light, New J. Chem. 2006, 50, 65-70.
59. A. Hamza, G. Schubert, T. Soós, I. Pápai, J. Am. Chem. Soc. 2006, 128, 13151-13160.
60. a) Q. Li, W. H. Yip, T. C. W. Mak, J. Inclusion Phenom. Mol. Recognit. Chem. 1995, 23, 233-244;
61. b) M. Boiocchi, L. Del Boca, D. Esteban Gomez, L. Fabbrizzi, M. Licchelli, J. Am. Chem. Soc. 2004, 126, 16507-16514;
62. c) Q. Li, T. C. W. Mak, J. Inclusion Phenom. Mol. Recognit. Chem. 1994, 20, 73-88;
63. d) E. R. Perez, R. H. A. Santos, M. T. P. Gambardella, L. G. M. de Macedo, U. P. Rodrigues-Filho, J.-C. Launay, D. W. Franco, J. Org. Chem. 2004, 69, 8005-8011;
64. e) T. C. W. Mak, F. Xue, J. Am. Chem. Soc. 2000, 122, 9860-9861;
65. f) T. Gunnlaugsson, P. E. Kruger, P. Jensen, F. M. Pfeffer, G. M. Hussey, Tetrahedron Lett. 2003, 44, 8909-8913.
66. a) P. A. Gale, J. Garric, M. E. Light, B. A. McNally, B. D. Smith, Chem. Commun. 2007, 1736-1738;
67. b) P. V. Santacroce, J. T. Davis, M. E. Light, P. A. Gale, J. C. Iglesias-Sánchez, P. Prados, R. Quesada, J. Am. Chem. Soc. 2007, 129, 1886-1887;
68. c) M. G. Fisher, P. A. Gale, M. E. Light, New J. Chem. 2007, 31, 1583-1584.
69. Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326.
70. G. M. Sheldrick, SADABS-Bruker Nonius area detector scaling and absorption correctionotherV2.10.
71. SHELX97: Programs for Crystal Structure Analysis (Release 97-2). G. M. Sheldrick, Institut für Anorganische Chemie der Universität, Göttingen, (Germany) 1998.