Facile purification of the N-heterocyclic carbene precursor [IMesH][Cl] and chloride binding in the solvates [IMesH][Cl]·acetone and [IMesH][Cl]·H2O (IMes = 1,3-bis(2,4,6-trimethylphenyl) imidazol-2-ylidene)

CrystEngComm

Volumn 6, Issue , 2004, Pages 173-176

  Cole, Marcus L ^a,b   Junk, Peter C ^a  

^a MONASH UNIVERSITY   (Australia)

^b UNIVERSITY OF ADELAIDE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; BENZYL THIOCYANATE; CARBENOID; CHLORIDE; HETEROCYCLIC COMPOUND; HYDROGEN; IMIDAZOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHLORIDE TRANSPORT; ENVIRONMENTAL TEMPERATURE; HYDRATION; HYDROGEN BOND; MOLECULAR STABILITY; PURIFICATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 10044252829     PISSN: 14668033     EISSN: None     Source Type: Journal    
DOI: 10.1039/b403451a     Document Type: Article

References (42)

1. A. J. Arduengo, R. L. Harlow and M. Kline, J. Am. Chem. Soc., 1991, 113, 361.
2. A. J. Arduengo, H. V. R. Dias, R. L. Harlow and M. Kline, J. Am. Chem. Soc., 1992, 114, 5530.
3. W. A. Herrmann, Angew. Chem. Int. Ed., 2002, 41, 1291.
4. D. Bourissou, O. Guerret, F. P. Gabbaï and G. Bertrand, Chem. Rev., 2000, 100, 39.
5. W. A. Herrmann and C. Köcher, Angew. Chem. Int. Ed., 1997, 36, 2162.
6. A. M. Magill, D. S. McGuinness, K. J. Cavell, G. J. P. Britovsek, V. C. Gibson, A. J. P. White, D. J. Williams, A. H. White and B. W. Skelton, J. Organomet. Chem., 2001, 617-618, 546.
7. A. A. D. Tulloch, A. A. Danopoulos, R. P. Tooze, S. M. Cafferkey, S. Kleinhenz and M. B. Hursthouse, Chem. Commun., 2000, 1247.
8. D. S. McGuinness and K. J. Cavell, Organometallics, 2000, 19, 741.
9. Applied Homogeneous Catalysis with Organometallic Complexes, ed. B. Cornils and W. A. Herrmann, VCH, Weinheim, 1996.
10. R. H. Grubbs, in Comprehensive Organometallic Chemistry, ed. G. Wilkinson, F. G. A. Stone and E. W. Abel, Pergamon, Oxford, UK, 1982, vol. 8.
11. M. Brookhart and W. B. Studabaker, Chem. Rev., 1987, 87, 411.
12. K. H. Dötz, in Organometallics in Organic Synthesis, ed. A. de Meijere and H. tom Dieck, Springer, Berlin, 1988.
13. J. Huang, H.-J. Schanz, E. D. Stevens and S. P. Nolan, Organometallics, 1999, 18, 2370 and references therein.
14. Of the 426 structures deposited with the CCDC that contain an imidazole-2-ylidene or 4,5-dihydroimidazol-2-ylidene coordinated to a metal through the 2-position (348 and 78, respectively), 47 employ the NHC IMes. (CSD version 5.25, November 2003).
15. From a survey of the CCDC, only 7 independent research ensembles have published structures containing IMes. (CSD version 5.25, November 2003).
16. A. J. Arduengo, US Patent, 1991, Patent No. 5 077 414.
17. M. H. Voges, C. Rømming and M. Tilset, Organometallics, 1999, 18, 529.
18. A. J. Arduengo, S. F. Gamper, M. Tamm, J. C. Calabrese, F. Davidson and H. A. Craig, J. Am. Chem. Soc., 1995, 117, 572.
19. M. L. Cole, C. Jones and P. C. Junk, New J. Chem., 2002, 1296.
20. For examples, see: (a) A. J. Arduengo, M. Kline, J. C. Calabrese and F. Davidson, J. Am. Chem. Soc., 1991, 113, 9704; (b) N. Kuhn, G. Henkel and T. Kratz, J. Chem. Soc., Chem., Commun., 1993, 1778; (c) A. J. Arduengo, F. Davidson, H. V. R. Dias, J. R. Goerlich, D. Khasnis, W. J. Marshall and T. K. Prakasha, J. Am. Chem. Soc., 1997, 119, 12742; (d) N. Kuhn, J. Fahl, R. Fawzi, C. Maichle-Mossmer and M. Steimann, Z. Naturforsch., 1998, 53b, 720.
21. For examples, see: (a) A. J. Arduengo, M. Kline, J. C. Calabrese and F. Davidson, J. Am. Chem. Soc., 1991, 113, 9704; (b) N. Kuhn, G. Henkel and T. Kratz, J. Chem. Soc., Chem., Commun., 1993, 1778; (c) A. J. Arduengo, F. Davidson, H. V. R. Dias, J. R. Goerlich, D. Khasnis, W. J. Marshall and T. K. Prakasha, J. Am. Chem. Soc., 1997, 119, 12742; (d) N. Kuhn, J. Fahl, R. Fawzi, C. Maichle-Mossmer and M. Steimann, Z. Naturforsch., 1998, 53b, 720.
22. For examples, see: (a) A. J. Arduengo, M. Kline, J. C. Calabrese and F. Davidson, J. Am. Chem. Soc., 1991, 113, 9704; (b) N. Kuhn, G. Henkel and T. Kratz, J. Chem. Soc., Chem., Commun., 1993, 1778; (c) A. J. Arduengo, F. Davidson, H. V. R. Dias, J. R. Goerlich, D. Khasnis, W. J. Marshall and T. K. Prakasha, J. Am. Chem. Soc., 1997, 119, 12742; (d) N. Kuhn, J. Fahl, R. Fawzi, C. Maichle-Mossmer and M. Steimann, Z. Naturforsch., 1998, 53b, 720.
23. For examples, see: (a) A. J. Arduengo, M. Kline, J. C. Calabrese and F. Davidson, J. Am. Chem. Soc., 1991, 113, 9704; (b) N. Kuhn, G. Henkel and T. Kratz, J. Chem. Soc., Chem., Commun., 1993, 1778; (c) A. J. Arduengo, F. Davidson, H. V. R. Dias, J. R. Goerlich, D. Khasnis, W. J. Marshall and T. K. Prakasha, J. Am. Chem. Soc., 1997, 119, 12742; (d) N. Kuhn, J. Fahl, R. Fawzi, C. Maichle-Mossmer and M. Steimann, Z. Naturforsch., 1998, 53b, 720.
24. Periodic Table of the Elements, ed. E. Fluck and K. G. Heumann, VCH, Weinheim, 1991.
25. The Hydrogen Bond, ed. P. Schuster, G. Zundel and C. Sandorfy, Amsterdam, 1976, vol. 2.
26. See mechanistic discussions of: M. K. Denk and J. M. Rodezno, J. Organomet. Chem., 2000, 608, 122 and reference 20(c).
27. For example, see: R. Boese, D. Blaser and N. Z. Kuhn, Kristallografiya, 1994, 209, 837.
28. For two non-IMesH examples where both interactions are evident, see: (a) A. J. Arduengo, H. V. R. Dias, R. L. Harlow and M. Kline, J. Am. Chem. Soc., 1992, 114, 5530; (b) W. A. Herrmann, L. J. Goossen, G. R. J. Artus and C. Köcher, Organometallics, 1997, 16, 2472.
29. For two non-IMesH examples where both interactions are evident, see: (a) A. J. Arduengo, H. V. R. Dias, R. L. Harlow and M. Kline, J. Am. Chem. Soc., 1992, 114, 5530; (b) W. A. Herrmann, L. J. Goossen, G. R. J. Artus and C. Köcher, Organometallics, 1997, 16, 2472.
30. A. J. Arduengo, R. Krafczyk, R. Schmutzler, H. A. Craig, J. R. Goerlich, W. J. Marshall and M. Unverzagt, Tetrahedron, 1999, 55, 14523.
31. From a survey of the CCDC, 18 compounds containing the NHC 1,3-bis(2,6-diisopropylphenyl) imidazole-2-ylidene or its related imidazolium salt have been deposited (CSD version 5.25, November 2003).
32. As confirmed by unit cell determinations on multiple crystals from the second crop. No block-like crystals, as per the morphology of 1, observed.
33. Purification of Laboratory Chemicals, ed. W. L. F. Armarego and D. D. Perrin, Pergamon, Oxford, UK, 1988.
34. Supramolecular Chemistry, ed. J. W. Steed and J. A. Atwood, Wiley, New York, 2000.
35. C. A. Ilioudis, K. S. B. Hancock, D. Georganopoulou and J. W. Steed, New J. Chem., 2000, 787.
36. Supramolecular Chemistry of Anions, ed. A. Bianchi, K. Bowman-James and E. Garcia-Espana, Wiley-VCH, New York, 1997.
37. F. P. Schmidtchen and M. Berger, Chem. Rev., 1997, 97, 1609.
38. Supramolecular Chemistry: Concepts and Perspectives, ed. J.-M. Lehn, VCH, Weinheim, 1995.
39. Z. Otwinowski, W. Minor, in Methods in Enzymology, 276: Macromolecular Crystallography, Part A, ed. C. W. Cater and R. M. Sweet, Academic Press, New York, 1997, p. 307.
40. G. M. Sheldrick, SHELXL-97; University of Göttingen, Germany, 1997.
41. G. M. Sheldrick, SHELXS-97; University of Göttingen, Germany, 1997.
42. L. G. Barbour, J. Supramol. Chem., 2001, 1, 189.