Selective solid-liquid extraction of lithium halide salts using a ditopic macrobicyclic receptor

Inorganic Chemistry

Volumn 43, Issue 24, 2004, Pages 7617-7621

  Mahoney, Joseph M ^a   Beatty, Alicia M ^a   Smith, Bradley D ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; HALIDE; LITHIUM; LITHIUM CHLORIDE; POTASSIUM CHLORIDE; RECEPTOR SUBTYPE; SODIUM CHLORIDE;

ARTICLE; METAL BINDING; METAL EXTRACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SEPARATION TECHNIQUE; X RAY CRYSTALLOGRAPHY;

BROMIDES; CHLORIDES; CRYSTALLOGRAPHY, X-RAY; IONS; LITHIUM; MACROMOLECULAR SUBSTANCES; MAGNETIC RESONANCE SPECTROSCOPY; MEMBRANES, ARTIFICIAL; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; POTASSIUM CHLORIDE; SALTS; SODIUM CHLORIDE; THERMODYNAMICS;

EID: 9444277816     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic049066b     Document Type: Article

References (41)

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5. Recent examples of dual receptor systems that simultaneously complex an anion and a cation: Byriel, K. A.; Gasperov, V.; Gloe, K.; Kennard, C. H. L.; Leong, A. J.; Lindoy, L. F.; Mahinay, M. S.; Pham, H. T.; Tasker, P. A.; Thorp, D.; Turner, P. Dalton Trans. 2003, 3034-3040. Cafeo, G.; Gargiulli, C.; Gattuso, G.; Kohnke, F. H.; Notti, A.; Occhipinti, S.; Pappalardo, S.; Parisi, M. F. Tetrahedron Lett. 2002, 43, 8103-8106. Cafeo, G.; Gattuso, G.; Kohnke, F. H.; Notti, A.; Occhipinti, S.; Pappalardo, S.; Parisi, M. F. Angew. Chem., Int. Ed. 2002, 41, 2122-2126. Qian, Q.; Wilson, G. S.; Bowman-James, K.; Girault, H. H. Anal. Chem. 2001, 73, 497-503. Kavallieratos, K.; Moyer, B. A. Chem. Comm. 2001, 1620-1621. Kavallieratos, K.; Sachleben, R. A.; Van Berkel, G. J.; Moyer, B. A. Chem. Comm. 2000, 187-188.
6. Recent examples of dual receptor systems that simultaneously complex an anion and a cation: Byriel, K. A.; Gasperov, V.; Gloe, K.; Kennard, C. H. L.; Leong, A. J.; Lindoy, L. F.; Mahinay, M. S.; Pham, H. T.; Tasker, P. A.; Thorp, D.; Turner, P. Dalton Trans. 2003, 3034-3040. Cafeo, G.; Gargiulli, C.; Gattuso, G.; Kohnke, F. H.; Notti, A.; Occhipinti, S.; Pappalardo, S.; Parisi, M. F. Tetrahedron Lett. 2002, 43, 8103-8106. Cafeo, G.; Gattuso, G.; Kohnke, F. H.; Notti, A.; Occhipinti, S.; Pappalardo, S.; Parisi, M. F. Angew. Chem., Int. Ed. 2002, 41, 2122-2126. Qian, Q.; Wilson, G. S.; Bowman-James, K.; Girault, H. H. Anal. Chem. 2001, 73, 497-503. Kavallieratos, K.; Moyer, B. A. Chem. Comm. 2001, 1620-1621. Kavallieratos, K.; Sachleben, R. A.; Van Berkel, G. J.; Moyer, B. A. Chem. Comm. 2000, 187-188.
7. Recent examples of dual receptor systems that simultaneously complex an anion and a cation: Byriel, K. A.; Gasperov, V.; Gloe, K.; Kennard, C. H. L.; Leong, A. J.; Lindoy, L. F.; Mahinay, M. S.; Pham, H. T.; Tasker, P. A.; Thorp, D.; Turner, P. Dalton Trans. 2003, 3034-3040. Cafeo, G.; Gargiulli, C.; Gattuso, G.; Kohnke, F. H.; Notti, A.; Occhipinti, S.; Pappalardo, S.; Parisi, M. F. Tetrahedron Lett. 2002, 43, 8103-8106. Cafeo, G.; Gattuso, G.; Kohnke, F. H.; Notti, A.; Occhipinti, S.; Pappalardo, S.; Parisi, M. F. Angew. Chem., Int. Ed. 2002, 41, 2122-2126. Qian, Q.; Wilson, G. S.; Bowman-James, K.; Girault, H. H. Anal. Chem. 2001, 73, 497-503. Kavallieratos, K.; Moyer, B. A. Chem. Comm. 2001, 1620-1621. Kavallieratos, K.; Sachleben, R. A.; Van Berkel, G. J.; Moyer, B. A. Chem. Comm. 2000, 187-188.
8. Recent examples of dual receptor systems that simultaneously complex an anion and a cation: Byriel, K. A.; Gasperov, V.; Gloe, K.; Kennard, C. H. L.; Leong, A. J.; Lindoy, L. F.; Mahinay, M. S.; Pham, H. T.; Tasker, P. A.; Thorp, D.; Turner, P. Dalton Trans. 2003, 3034-3040. Cafeo, G.; Gargiulli, C.; Gattuso, G.; Kohnke, F. H.; Notti, A.; Occhipinti, S.; Pappalardo, S.; Parisi, M. F. Tetrahedron Lett. 2002, 43, 8103-8106. Cafeo, G.; Gattuso, G.; Kohnke, F. H.; Notti, A.; Occhipinti, S.; Pappalardo, S.; Parisi, M. F. Angew. Chem., Int. Ed. 2002, 41, 2122-2126. Qian, Q.; Wilson, G. S.; Bowman-James, K.; Girault, H. H. Anal. Chem. 2001, 73, 497-503. Kavallieratos, K.; Moyer, B. A. Chem. Comm. 2001, 1620-1621. Kavallieratos, K.; Sachleben, R. A.; Van Berkel, G. J.; Moyer, B. A. Chem. Comm. 2000, 187-188.
9. Recent examples of dual receptor systems that simultaneously complex an anion and a cation: Byriel, K. A.; Gasperov, V.; Gloe, K.; Kennard, C. H. L.; Leong, A. J.; Lindoy, L. F.; Mahinay, M. S.; Pham, H. T.; Tasker, P. A.; Thorp, D.; Turner, P. Dalton Trans. 2003, 3034-3040. Cafeo, G.; Gargiulli, C.; Gattuso, G.; Kohnke, F. H.; Notti, A.; Occhipinti, S.; Pappalardo, S.; Parisi, M. F. Tetrahedron Lett. 2002, 43, 8103-8106. Cafeo, G.; Gattuso, G.; Kohnke, F. H.; Notti, A.; Occhipinti, S.; Pappalardo, S.; Parisi, M. F. Angew. Chem., Int. Ed. 2002, 41, 2122-2126. Qian, Q.; Wilson, G. S.; Bowman-James, K.; Girault, H. H. Anal. Chem. 2001, 73, 497-503. Kavallieratos, K.; Moyer, B. A. Chem. Comm. 2001, 1620-1621. Kavallieratos, K.; Sachleben, R. A.; Van Berkel, G. J.; Moyer, B. A. Chem. Comm. 2000, 187-188.
10. Recent examples of dual receptor systems that simultaneously complex an anion and a cation: Byriel, K. A.; Gasperov, V.; Gloe, K.; Kennard, C. H. L.; Leong, A. J.; Lindoy, L. F.; Mahinay, M. S.; Pham, H. T.; Tasker, P. A.; Thorp, D.; Turner, P. Dalton Trans. 2003, 3034-3040. Cafeo, G.; Gargiulli, C.; Gattuso, G.; Kohnke, F. H.; Notti, A.; Occhipinti, S.; Pappalardo, S.; Parisi, M. F. Tetrahedron Lett. 2002, 43, 8103-8106. Cafeo, G.; Gattuso, G.; Kohnke, F. H.; Notti, A.; Occhipinti, S.; Pappalardo, S.; Parisi, M. F. Angew. Chem., Int. Ed. 2002, 41, 2122-2126. Qian, Q.; Wilson, G. S.; Bowman-James, K.; Girault, H. H. Anal. Chem. 2001, 73, 497-503. Kavallieratos, K.; Moyer, B. A. Chem. Comm. 2001, 1620-1621. Kavallieratos, K.; Sachleben, R. A.; Van Berkel, G. J.; Moyer, B. A. Chem. Comm. 2000, 187-188.
11. For recent papers that discuss ditopic salt-binding receptors, see: Turner, D. R.; Spencer, E. C.; Howard, J. A. K.; Tocher, D. A.; Steed, J. W. Chem. Commun. 2004, 1352-1353. Plieger, P. G.; Tasker, P. A.; Galbraith, S. G. Dalton Trans. 2004, 313-318. Pajewski, R.; Ferdani, R.; Schlesinger, P. H.; Gokel, G. W. Chem. Commun. 2004, 160-161. Zhou, L.; Sun, H.; Li, H.; Wang, H.; Zhang, X.; Wu, S.; Lee, S. Org. Lett. 2004, 6, 1071-1074. Gale, P. A. Coord. Chem. Rev. 2003, 240, 191-221. Shukla, R.; Kida, T.; Smith, B. D. Org. Lett. 2000, 2, 3039-3248. Deetz, M. J.; Shang, M.; Smith, B. D. J. Am. Chem. Soc. 2000, 122, 6201-6207.
12. For recent papers that discuss ditopic salt-binding receptors, see: Turner, D. R.; Spencer, E. C.; Howard, J. A. K.; Tocher, D. A.; Steed, J. W. Chem. Commun. 2004, 1352-1353. Plieger, P. G.; Tasker, P. A.; Galbraith, S. G. Dalton Trans. 2004, 313-318. Pajewski, R.; Ferdani, R.; Schlesinger, P. H.; Gokel, G. W. Chem. Commun. 2004, 160-161. Zhou, L.; Sun, H.; Li, H.; Wang, H.; Zhang, X.; Wu, S.; Lee, S. Org. Lett. 2004, 6, 1071-1074. Gale, P. A. Coord. Chem. Rev. 2003, 240, 191-221. Shukla, R.; Kida, T.; Smith, B. D. Org. Lett. 2000, 2, 3039-3248. Deetz, M. J.; Shang, M.; Smith, B. D. J. Am. Chem. Soc. 2000, 122, 6201-6207.
13. For recent papers that discuss ditopic salt-binding receptors, see: Turner, D. R.; Spencer, E. C.; Howard, J. A. K.; Tocher, D. A.; Steed, J. W. Chem. Commun. 2004, 1352-1353. Plieger, P. G.; Tasker, P. A.; Galbraith, S. G. Dalton Trans. 2004, 313-318. Pajewski, R.; Ferdani, R.; Schlesinger, P. H.; Gokel, G. W. Chem. Commun. 2004, 160-161. Zhou, L.; Sun, H.; Li, H.; Wang, H.; Zhang, X.; Wu, S.; Lee, S. Org. Lett. 2004, 6, 1071-1074. Gale, P. A. Coord. Chem. Rev. 2003, 240, 191-221. Shukla, R.; Kida, T.; Smith, B. D. Org. Lett. 2000, 2, 3039-3248. Deetz, M. J.; Shang, M.; Smith, B. D. J. Am. Chem. Soc. 2000, 122, 6201-6207.
14. For recent papers that discuss ditopic salt-binding receptors, see: Turner, D. R.; Spencer, E. C.; Howard, J. A. K.; Tocher, D. A.; Steed, J. W. Chem. Commun. 2004, 1352-1353. Plieger, P. G.; Tasker, P. A.; Galbraith, S. G. Dalton Trans. 2004, 313-318. Pajewski, R.; Ferdani, R.; Schlesinger, P. H.; Gokel, G. W. Chem. Commun. 2004, 160-161. Zhou, L.; Sun, H.; Li, H.; Wang, H.; Zhang, X.; Wu, S.; Lee, S. Org. Lett. 2004, 6, 1071-1074. Gale, P. A. Coord. Chem. Rev. 2003, 240, 191-221. Shukla, R.; Kida, T.; Smith, B. D. Org. Lett. 2000, 2, 3039-3248. Deetz, M. J.; Shang, M.; Smith, B. D. J. Am. Chem. Soc. 2000, 122, 6201-6207.
15. For recent papers that discuss ditopic salt-binding receptors, see: Turner, D. R.; Spencer, E. C.; Howard, J. A. K.; Tocher, D. A.; Steed, J. W. Chem. Commun. 2004, 1352-1353. Plieger, P. G.; Tasker, P. A.; Galbraith, S. G. Dalton Trans. 2004, 313-318. Pajewski, R.; Ferdani, R.; Schlesinger, P. H.; Gokel, G. W. Chem. Commun. 2004, 160-161. Zhou, L.; Sun, H.; Li, H.; Wang, H.; Zhang, X.; Wu, S.; Lee, S. Org. Lett. 2004, 6, 1071-1074. Gale, P. A. Coord. Chem. Rev. 2003, 240, 191-221. Shukla, R.; Kida, T.; Smith, B. D. Org. Lett. 2000, 2, 3039-3248. Deetz, M. J.; Shang, M.; Smith, B. D. J. Am. Chem. Soc. 2000, 122, 6201-6207.
16. For recent papers that discuss ditopic salt-binding receptors, see: Turner, D. R.; Spencer, E. C.; Howard, J. A. K.; Tocher, D. A.; Steed, J. W. Chem. Commun. 2004, 1352-1353. Plieger, P. G.; Tasker, P. A.; Galbraith, S. G. Dalton Trans. 2004, 313-318. Pajewski, R.; Ferdani, R.; Schlesinger, P. H.; Gokel, G. W. Chem. Commun. 2004, 160-161. Zhou, L.; Sun, H.; Li, H.; Wang, H.; Zhang, X.; Wu, S.; Lee, S. Org. Lett. 2004, 6, 1071-1074. Gale, P. A. Coord. Chem. Rev. 2003, 240, 191-221. Shukla, R.; Kida, T.; Smith, B. D. Org. Lett. 2000, 2, 3039-3248. Deetz, M. J.; Shang, M.; Smith, B. D. J. Am. Chem. Soc. 2000, 122, 6201-6207.
17. For recent papers that discuss ditopic salt-binding receptors, see: Turner, D. R.; Spencer, E. C.; Howard, J. A. K.; Tocher, D. A.; Steed, J. W. Chem. Commun. 2004, 1352-1353. Plieger, P. G.; Tasker, P. A.; Galbraith, S. G. Dalton Trans. 2004, 313-318. Pajewski, R.; Ferdani, R.; Schlesinger, P. H.; Gokel, G. W. Chem. Commun. 2004, 160-161. Zhou, L.; Sun, H.; Li, H.; Wang, H.; Zhang, X.; Wu, S.; Lee, S. Org. Lett. 2004, 6, 1071-1074. Gale, P. A. Coord. Chem. Rev. 2003, 240, 191-221. Shukla, R.; Kida, T.; Smith, B. D. Org. Lett. 2000, 2, 3039-3248. Deetz, M. J.; Shang, M.; Smith, B. D. J. Am. Chem. Soc. 2000, 122, 6201-6207.
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20. Mahoney, J. M.; Beatty, A. M.; Smith, B. D. J. Am. Chem. Soc. 2001, 123, 5847-5848. Mahoney, J. M.; Marshall, R. A.; Beatty, A. M.; Smith, B. D.; Camiolo, S.; Gale, P. A. J. Supramol. Chem. 2001, 1, 289-292. Mahoney, J. M.; Davis, J. P.; Smith, B. D. J. Org. Chem. 2003, 68, 9819-6820.
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23. Examples of solid-liquid extraction of lithium salts with weakly competitive counteranions include the following: Inokuma, S.; Takezawa, M.; Satoh, H.; Nakamura, Y.; Sasaki, T.; Nishimura, J. J. Org. Chem. 1998, 63, 5791-5796. Inokuma, S.; Yamamoto, T.; Nishimura, J. J. Org. Chem. 1990, 31, 97-100. Nishizawa, K.; Takano, T.; Ikeda, I.; Okahara, M. Sep. Sci. Technol. 1988, 23, 333-343.
24. Examples of solid-liquid extraction of lithium salts with weakly competitive counteranions include the following: Inokuma, S.; Takezawa, M.; Satoh, H.; Nakamura, Y.; Sasaki, T.; Nishimura, J. J. Org. Chem. 1998, 63, 5791-5796. Inokuma, S.; Yamamoto, T.; Nishimura, J. J. Org. Chem. 1990, 31, 97-100. Nishizawa, K.; Takano, T.; Ikeda, I.; Okahara, M. Sep. Sci. Technol. 1988, 23, 333-343.
25. Examples of solid-liquid extraction of lithium salts with weakly competitive counteranions include the following: Inokuma, S.; Takezawa, M.; Satoh, H.; Nakamura, Y.; Sasaki, T.; Nishimura, J. J. Org. Chem. 1998, 63, 5791-5796. Inokuma, S.; Yamamoto, T.; Nishimura, J. J. Org. Chem. 1990, 31, 97-100. Nishizawa, K.; Takano, T.; Ikeda, I.; Okahara, M. Sep. Sci. Technol. 1988, 23, 333-343.
26. The unit cell in the [1·LiBr] crystal contains four independent but structurally similar complexes.
27. Olsher, U.; Izatt, R.; Bradshaw, J. S.; Dalley, N. K. Chem. Rev. 1991, 91, 137-164. Boulatov, R.; Du, B.; Meyers, E. A.; Shore, S. G. Inorg. Chem. 1999, 38, 4554-4558. Chivers, T.; Downard, A.; Parvez, M.; Schatte, G. Inorg. Chem. 2001, 40, 1975-1977.
28. Olsher, U.; Izatt, R.; Bradshaw, J. S.; Dalley, N. K. Chem. Rev. 1991, 91, 137-164. Boulatov, R.; Du, B.; Meyers, E. A.; Shore, S. G. Inorg. Chem. 1999, 38, 4554-4558. Chivers, T.; Downard, A.; Parvez, M.; Schatte, G. Inorg. Chem. 2001, 40, 1975-1977.
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32. 3 are all less than 0.02 mg/mL.
33. Snaith, R.; Wright, D. S. In Lithium Chemistry-A Theoretical and Experimental Overview; Sapse, A.-M., Schleyer, P. v. R., Eds.; Wiley: New York, 1995; Chapter 8.
34. Excellent lithium salt solubility is often seen when the solvent contains a polar aprotic additive (such as TMEDA or HMPA) that can coordinate to the lithium and produce solvated ion-pair aggregates with an ionic core and an organic periphery.
35. A property that in many ways is analogous to hydration energy is the salt lattice energy, which in the case of chloride salts is LiCl (834 kJ/mol) > NaCl (769 kJ/mol) > KCl (701 kJ/mol) > CsCl (657 kJ/ mol). However, this property does not correlate with solubility of the solid salt in an organic solvent.
36. Receptor 1 appears to bind the sodium and potassium salts in solution as contact ion pairs and most likely binds the lithium salts as water-separated ion pairs (as illustrated in Figures 1 and 2), where the water is derived adventitiously from the atmosphere. The question arises whether receptor 1 can bind the lithium salts in extremely anhydrous solution as contact ion pairs; however, this is a technically difficult experiment to conduct in an unambiguous manner and was not attempted.
37. It is possible that receptor 1 accelerates the solubilization process by removing associated ion pairs directly from the solid surface.
38. a values; however, the literature data (see ref 2 and references therein) strongly suggest that receptor 1 does not have a selective affinity for lithium salts over sodium or potassium salts.
39. Several ditopic receptors that likely bind salts as separated ion pairs have been reported to be poor solubilizers of solid alkali metal chlorides: Webber, P. R. A.; Beer, P. D. Dalton Trans. 2003, 2249-2252. Evans, A. J.; Beer, P. D. Dalton Trans. 2003, 4451-4456. Tumcharern, G.; Tuntulani, T.; Coles, S. J.; Hursthouse, M. B.; Kilburn, J. D. Org. Lett. 2003, 5, 4971-4974.
40. Several ditopic receptors that likely bind salts as separated ion pairs have been reported to be poor solubilizers of solid alkali metal chlorides: Webber, P. R. A.; Beer, P. D. Dalton Trans. 2003, 2249-2252. Evans, A. J.; Beer, P. D. Dalton Trans. 2003, 4451-4456. Tumcharern, G.; Tuntulani, T.; Coles, S. J.; Hursthouse, M. B.; Kilburn, J. D. Org. Lett. 2003, 5, 4971-4974.
41. Several ditopic receptors that likely bind salts as separated ion pairs have been reported to be poor solubilizers of solid alkali metal chlorides: Webber, P. R. A.; Beer, P. D. Dalton Trans. 2003, 2249-2252. Evans, A. J.; Beer, P. D. Dalton Trans. 2003, 4451-4456. Tumcharern, G.; Tuntulani, T.; Coles, S. J.; Hursthouse, M. B.; Kilburn, J. D. Org. Lett. 2003, 5, 4971-4974.