-B(OH)2 versus -OH in supramolecular synthesis: Molecular complexes of 4-hydroxyphenylboronic acid with aza-donor compounds

Tetrahedron Letters

Volumn 51, Issue 52, 2010, Pages 6901-6905

  Talwelkar, Mayura ^a   Pedireddi, V R ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BHUBANESWAR   (India)

Author keywords

Boronic acid; Co crystallization; Hydrogen bonds; Molecular recognition

Indexed keywords

BENZENEBORONIC ACID;

ARTICLE; CHEMICAL INTERACTION; COMPARATIVE STUDY; CRYSTALLIZATION; HYDROGEN BOND; SUPRAMOLECULAR SYNTHESIS; SYNTHESIS;

EID: 78650676959     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.126     Document Type: Article

References (57)

1. (a) Lehn, J. M. Angew. Chem., Int. Ed. 1990, 29, 1304-1319;
2. (b) Desiraju, G. R. Angew. Chem., Int. Ed. 1995, 34, 2311-2327;
3. (c) Pedireddi, V. R.; Chatterjee, S.; Ranganathan, A.; Rao, C. N. R. J. Am. Chem. Soc. 1997, 119, 10867-10868;
4. (d) Hosseini, M. W. Acc. Chem. Res. 2005, 38, 313-323;
5. (e) Aakeroy, C. B.; Beatty, A. M.; Helfrich, B. A. Angew. Chem., Int. Ed. 2001, 40, 3240-3242;
6. (f) Shan, N.; Batchelor, E.; Jones, W. Tetrahedron Lett. 2002, 43, 8721-8725;
7. (g) Arora, K. K.; Pedireddi, V. R. J. Org. Chem. 2003, 68, 9177-9185.
8. (a) Lehn, J. M. Supramolecular Chemistry; VCH: Weinheim, 1995;
9. (b) Atwood, J. L.; Davies, E. D.; MacNicol, D. D.; Vögtle, F. Comprehensive Supramolecular Chemistry; Oxford: Pergamon, 1996.
10. (a) Dunitz, J. D.; Gavezzotti, A. Angew. Chem., Int. Ed. 2005, 44, 1766-1787;
11. (b) Jones, W.; Rao, C. N. R. Supramolecular Organization and Materials Design; Cambridge University Press, 2002;
12. (c) Hollingsworth, M. D. Science 2002, 295, 2410-2413;
13. (d) Lehn, J. M.; Mascal, M.; Decian, A.; Fischer, J. J. Chem. Soc., Chem. Commun. 1990, 479-481;
14. (e) Braga, D.; Grepioni, F. Angew. Chem., Int. Ed. 2004, 43, 4002-4011;
15. (f) Biradha, K. Cryst. Eng. Commun. 2003, 5, 374-384;
16. (g) Harris, K. D. M.; Stainton, N. M.; Callan, A. M.; Howie, R. A. J. Mater. Chem. 1993, 3, 947-952;
17. (h) Ahn, S.; PrakashaReddy, J.; Kariuki, B. M.; Chatterjee, S.; Ranganathan, A.; Pedireddi, V. R.; Rao, C. N. R.; Harris, K. D. M. Chem. Eur. J. 2005, 11, 2433-2439.
18. (a) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37-44;
19. (b) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401;
20. (c) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2382-2426;
21. (d) Sijbesma, R. P.; Meijer, E. W. Chem. Commun. 2003, 5-16;
22. (e) Guo, F.; Cheung, E. Y.; Harris, K. D. M.; Pedireddi, V. R. Cryst. Growth Des. 2006, 6, 846-848;
23. (f) Lee, S. O.; Kariuki, B. M.; Harris, K. D. M. New J. Chem. 2005, 29, 1266-1271;
24. (g) Cheung, E. Y.; David, S. E.; Harris, K. D. M.; Conway, B. R.; Timmins, P. J. Solid State Chem. 2007, 180, 1068-1075.
25. (a) Pedireddi, V. R.; SeethaLekshmi, N. Tetrahedron Lett. 2004, 45, 1903-1906;
26. (b) Rodriguez-Cuamatzi, P.; Vargas-Diaz, G.; Hopfl, H. Angew. Chem., Int. Ed. 2004, 43, 3041-3044;
27. (c) SeethaLekshmi, N.; Pedireddi, V. R. Cryst. Growth Des. 2007, 7, 944-949;
28. (d) Shimpi, M. R.; SeethaLekshmi, N.; Pedireddi, V. R. Cryst. Growth Des. 2007, 7, 1958-1963;
29. (e) Wan, S.; Guo, J.; Kim, J.; Ihee, H.; Jiang, D. Angew. Chem., Int. Ed. 2009, 48, 5439-5442;
30. (f) Rodriguez-Cuamatzi, P.; Luna- Garcia, R.; Torres-Huerta, A.; Bernal-Uruchurtu, M. I.; Barba, V.; Hopfl, H. Cryst. Growth Des. 2009, 9, 1575-1583.
31. (a) SeethaLekshmi, N.; Pedireddi, V. R. Inorg. Chem. 2006, 45, 2400-2402;
32. (b) Aakeroy, C. B.; Desper, J.; Urbina, J. F. Cryst. Eng. Commun. 2005, 7, 193-201;
33. (c) Rodriguez-Cuamatzi, P.; rillo-Flores, O. I.; Bernal-Uruchurtu, M. I.; Hopfl, H. Cryst. Growth Des. 2005, 5, 167-175;
34. (d) Christinat, N.; Scopelliti, R.; Severin, K. Angew. Chem., Int. Ed. 2008, 47, 1848-1852;
35. (e) Maly, K. E.; Maris, T.; Wuest, J. D. Cryst. Eng. Commun. 2006, 8, 33-35.
36. Allen, F. H.; Kennard, O. Chem. Des. Automat. News 1993, 8, 31.
37. (a) Pedireddi, V. R.; Prakashareddy, J.; Arora, K. K. Tetrahedron Lett. 2003, 44, 4857-4860;
38. (b) Prakashareddy, J.; Pedireddi, V. R. Tetrahedron 2004, 60, 8817-8827;
39. (c) Weinstein, S.; Leiserowitz, L.; Gilav, E. J. Am. Chem. Soc. 1980, 102, 2768-2772;
40. (d) Garciatellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265-9269;
41. (e) Lewis, F. D.; Yang, J. S. J. Phys. Chem. B 1997, 101, 1775-1781;
42. (f) Reddy, L. S.; Nangia, A.; Lynch, V. M. Cryst. Growth Des. 2004, 4, 89-94;
43. (g) McMahon, J. A.; Bis, J. A.; Vishweshwar, P.; Shattock, T. R.; McLaughlin, O. L.; Zaworotko, M. J. Z. Kristallogr. 2005, 220, 340-350.
44. (a) Varughese, S.; Pedireddi, V. R. Chem. Eur. J. 2006, 12, 1597-1609;
45. (b) Frišçic, T.; MacGillivray, L. R. Chem. Commun. 2005, 5748-5750;
46. (c) Delori, A.; Suresh, E.; Pedireddi, V. R. Chem. Eur. J. 2008, 14, 6967-6977;
47. (d) Bis, J. A.; Zaworotko, M.J. Cryst. Growth Des. 2005, 5, 1169-1179;
48. (e) Han, J. J.; Yau, C. W.; Lam, C. K.; Mak, T. C. W. J. Am. Chem. Soc. 2008, 130, 10315-10326;
49. (f) Pedireddi, V. R.; Chatterjee, S.; Ranganathan, A.; Rao, C. N. R. Tetrahedron 1998, 54, 9457-9474;
50. (g) Bernstein, J.; Etter, M. C.; MacDonald, J. C. J. Chem. Soc., Perkin Trans. 1990, 695-698;
51. (h) Shattock, T. R.; Arora, K. K.; Vishweshwar, P.; Zaworotko, M. J. Cryst. Growth Des. 2008, 8, 4533-4545;
52. (i) Biradha, K.; Zaworotko, M. J. J. Am. Chem. Soc. 1998, 120, 6431-6432;
53. (j) Papaefstathiou, G. S.; MacGillivray, L. R. Org. Lett. 2001, 3, 3835-3837.
54. (a) Shivachev, B.; Petrova, R.; Naydenova, E. Acta Crystallogr., Sect. E 2006, 62, o3887-o3889;
55. (b) Aakeröy, C. B.; Desper, J.; Levin, B.; Salmon, D. J. Trans. Am. Crystallogr. Assoc. 2004, 39, 123.
56. 2 = 0.3867 for 3194 reflections (I >2σ(I)), CCDC 745866.
57. The R-factors for 1e and 1e′ are found to be higher than the other structures, 1a-1d, but the authenticity of the homogeneity is established by powder patterns as given in Supplementary data (Fig. S1, ESI†)