Determination of labile chiral supramolecular ion pairs by chromatographic NMR spectroscopy

Angewandte Chemie - International Edition

Volumn 52, Issue 11, 2013, Pages 3255-3258

  Reddy G N , Manjunatha ^a,b   Ballesteros Garrido, Rafael ^c   Lacour, Jérôme ^c   Caldarelli, Stefano ^a,b  

^a AIX MARSEILLE UNIVERSITÉ   (France)

^b ECOLE POLYTECHNIQUE   (France)

^c UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

chiral recognition; ion pairs; NMR spectroscopy; stereochemistry; structure elucidation

Indexed keywords

CHIRAL RECOGNITION; CONFIGURATIONALLY; ION PAIRS; NMR DIFFUSOMETRY; STRUCTURE ELUCIDATION; SUPRAMOLECULAR ION; TIME-SCALES;

LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SILICA; STEREOCHEMISTRY; SUPRAMOLECULAR CHEMISTRY;

IONS;

EID: 84874857292     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201209616     Document Type: Article

References (67)

1. C. Zuccaccia, G. Bellachioma, G. Cardaci, A. Macchioni, Organometallics 2000, 19, 4663-4665
2. A. Macchioni, Eur. J. Inorg. Chem. 2003, 195-205
3. C. Zuccaccia, N. G. Stahl, A. Macchioni, M. C. Chen, J. A. Roberts, T. J. Marks, J. Am. Chem. Soc. 2004, 126, 1448-1464
4. G. Bellachioma, G. Ciancaleoni, C. Zuccaccia, D. Zuccaccia, A. Macchioni, Coord. Chem. Rev. 2008, 252, 2224-2238
5. A. Macchioni, G. Ciancaleoni, C. Zuccaccia, D. Zuccaccia, Chem. Soc. Rev. 2008, 37, 479-489.
6. P. Thureau, A. Thévand, B. Ancian, P. Escavabaja, G. S. Armstrong, V. A. Mandelshtam, ChemPhysChem 2005, 6, 1510-1513.
7. J. S. Kavakka, I. Kilpelainen, S. Heikkinen, Org. Lett. 2009, 11, 1349-1352
8. J. S. Kavakka, V. Parviainen, K. Wahala, I. Kilpelainen, S. Heikkinen, Magn. Reson. Chem. 2010, 48, 777-781
9. K. F. Morris, P. Stilbs, C. S. Johnson, Anal. Chem. 1994, 66, 211-215
10. R. Evans, S. Haiber, M. Nilsson, G. A. Morris, Anal. Chem. 2009, 81, 4548-4550
11. C. F. Tormena, R. Evans, S. Haiber, M. Nilsson, G. A. Morris, Magn. Reson. Chem. 2010, 48, 550-553
12. R. W. Adams, J. A. Aguilar, J. Cassani, G. A. Morris, M. Nilsson, Org. Biomol. Chem. 2011, 9, 7062
13. C. F. Tormena, R. Evans, S. Haiber, M. Nilsson, G. A. Morris, Magn. Reson. Chem. 2012, 50, 458-465
14. R. E. Hoffman, H. Arzuan, C. Pemberton, A. Aserin, N. Garti, J. Magn. Reson. 2008, 194, 295-299
15. C. Pemberton, R. Hoffman, A. Aserin, N. Garti, J. Magn. Reson. 2011, 208, 262-269
16. C. Pemberton, R. E. Hoffman, A. Aserin, N. Garti, Langmuir 2011, 27, 4497-4504
17. R. E. Hoffman, A. Aserin, N. Garti, J. Magn. Reson. 2012, 220, 18-25.
18. A. K. Rogerson, J. A. Aguilar, M. Nilsson, G. A. Morris, Chem. Commun. 2011, 47, 7063-7064.
19. S. Caldarelli, Magn. Reson. Chem. 2007, 45, S 48 -S 55.
20. S. Viel, F. Ziarelli, S. Caldarelli, Proc. Natl. Acad. Sci. USA 2003, 100, 9696-9698
21. G. Pages, C. Delaurent, S. Caldarelli, Angew. Chem. 2006, 118, 6096-6099
22. Angew. Chem. Int. Ed. 2006, 45, 5950-5953
23. G. Pages, C. Delaurent, S. Caldarelli, Anal. Chem. 2006, 78, 561-566
24. C. Carrara, S. Viel, C. Delaurent, F. Ziarelli, G. Excoffier, S. Caldarelli, J. Magn. Reson. 2008, 194, 303-306.
25. C. Carrara, Université Paul Cézanne (Marseille), 2009
26. C. Carrara, G. Pages, C. Delaurent, S. Viel, S. Caldarelli, J. Phys. Chem. C 2011, 115, 18776-18781
27. C. Carrara, S. Caldarelli, J. Phys. Chem. C 2012, 116, 20030-20034
28. C. Carrara, C. Lopez, S. Caldarelli, J. Chromatogr. A 2012, 1257, 204-207.
29. A. Von Zelewsky, Stereochemistry of Coordination Compounds, 1 st ed., Wiley, Chichester, UK, 1996
30. H. Amouri, M. Gruselle, Chirality in transition metal chemistry: molecules, supramolecular assemblies and materials, Wiley, Chichester, UK, 2008.
31. J. Lacour, C. Ginglinger, C. Grivet, G. Bernardinelli, Angew. Chem. 1997, 109, 660-662
32. Angew. Chem. Int. Ed. Engl. 1997, 36, 608-609.
33. F. Favarger, C. Goujon-Ginglinger, D. Monchaud, J. Lacour, J. Org. Chem. 2004, 69, 8521-8524.
34. J. Lacour, V. Hebbe-Viton, Chem. Soc. Rev. 2003, 32, 373-382
35. J. Lacour, D. Moraleda, Chem. Commun. 2009, 7073-7089
36. J. Lacour, C. R. Chim. 2010, 13, 985-997.
37. J. Lacour, S. Torche-Haldimann, J. J. Jodry, C. Ginglinger, F. Favarger, Chem. Commun. 1998, 1733-1734
38. J. Lacour, C. Goujon-Ginglinger, S. Torche-Haldimann, J. J. Jodry, Angew. Chem. 2000, 112, 3830-3832
39. Angew. Chem. Int. Ed. 2000, 39, 3695-3697
40. O. Maury, J. Lacour, H. Le Bozec, Eur. J. Inorg. Chem. 2001, 201-204
41. G. Bruylants, C. Bresson, A. Boisdenghien, F. Pierard, A. Kirsch-De Mesmaeker, J. Lacour, K. Bartik, New J. Chem. 2003, 27, 748-751
42. M. Gruselle, R. Thouvenot, W. Caspar, K. Boubekeur, H. Amouri, M. Ivanov, K. Tonsuaadu, Mendeleev Commun. 2004, 14, 282-283
43. I. Correia, H. Amouri, C. Cordier, Organometallics 2007, 26, 1150-1156
44. L. Mimassi, C. Cordier, C. Guyard-Duhayon, B. E. Mann, H. Amouri, Organometallics 2007, 26, 860-864.
45. R. Frantz, A. Pinto, S. Constant, G. Bernardinelli, J. Lacour, Angew. Chem. 2005, 117, 5188-5192
46. Angew. Chem. Int. Ed. 2005, 44, 5060-5064.
47. D. Monchaud, J. Lacour, C. Coudret, S. Fraysse, J. Organomet. Chem. 2001, 624, 388-391.
48. Discrimination in solution of diastereomeric salts of hexacoordinated phosphate anions and organic chiral cations using PFG-NMR has been attempted before, and resulted in very mild differences of the observed diffusion coefficients. See:, E. Martínez-Viviente, P. S. Pregosin, L. Vial, C. Herse, J. Lacour, Chem. Eur. J. 2004, 10, 2912-2918.
49. J. Lacour, J. J. Jodry, C. Ginglinger, S. Torche-Haldimann, Angew. Chem. 1998, 110, 2522-2524
50. Angew. Chem. Int. Ed. 1998, 37, 2379-2380.
51. D. Monchaud, J. J. Jodry, D. Pomeranc, V. Heitz, J.-C. Chambron, J.-P. Sauvage, a. J. Lacour, Angew. Chem. 2002, 114, 2423-2425
52. Angew. Chem. Int. Ed. 2002, 41, 2317-2319.
53. The enantiomers of tris(diimine)iron complexes can be separated by dynamic CSP-HPLC and their barrier of enantiomerization can be determined. See:, C. Villani, F. Gasparrini, M. Pierini, S. L. Mortera, I. D'Acquarica, A. Ciogli, G. Zappia, Chirality 2009, 21, 97-103.
54. E. C. Constable, R. Frantz, C. E. Housecroft, J. Lacour, A. Mahmood, Inorg. Chem. 2004, 43, 4817-4819
55. S. D. Bergman, R. Frantz, D. Gut, M. Kol, J. Lacour, Chem. Commun. 2006, 850-852
56. R. Frantz, E. Guillamón, J. Lacour, R. Llusar, V. Polo, C. Vicent, Inorg. Chem. 2007, 46, 10717-10723
57. H. S. Chow, E. C. Constable, R. Frantz, C. E. Housecroft, J. Lacour, M. Neuburger, D. Rappoport, S. Schaffner, New J. Chem. 2009, 33, 376-385.
58. J. Courtois, G. Fischer, S. Schauff, K. Albert, K. Irgum, Anal. Chem. 2006, 78, 580-584
59. V. Friebolin, M. P. Bayer, M. T. Matyska, J. J. Pesek, K. Albert, J. Sep. Sci. 2009, 32, 1722-1728
60. V. Friebolin, S. Marten, K. Albert, Magn. Reson. Chem. 2010, 48, 111-116
61. H. Händel, E. Gesele, K. Gottschall, K. Albert, Angew. Chem. 2003, 115, 454-458
62. Angew. Chem. Int. Ed. 2003, 42, 438-442
63. C. Hellriegel, U. Skogsberg, K. Albert, M. Lammerhofer, N. M. Maier, W. Lindner, J. Am. Chem. Soc. 2004, 126, 3809-3816
64. S. Schauff, V. Friebolin, M. D. Grynbaum, C. Meyer, K. Albert, Anal. Chem. 2007, 79, 8323-8326
65. U. Skogsberg, H. Handel, D. Sanchez, K. Albert, J. Chromatogr. A 2004, 1023, 215-223
66. U. Skogsberg, C. Meyer, J. Rehbein, G. Fischer, S. Schauff, N. Welsch, K. Albert, A. J. Hall, B. Sellergren, Polymer 2007, 48, 229-238.
67. S. Caldarelli, in Annual Report on NMR Spectroscopy, Vol. 73 (Ed.:, A. W. Graham,), Academic Press, New York, 2011, pp. 159-173.