Liquid-liquid extraction of pertechnetic acid (TcVII) by tri-n-butyl phosphate: Where is the proton? A molecular dynamics investigation

Journal of Physical Chemistry B

Volumn 115, Issue 10, 2011, Pages 2338-2348

  Schurhammer, Rachel ^a   Wipff, Georges ^a  

^a UMR 7509 du CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

HEXANE; HYDRATES; LIQUIDS; MOLECULAR DYNAMICS; PARAFFINS; PHASE INTERFACES; PROTONS; SOLVENT EXTRACTION;

ACIDIC WATER; AQUEOUS INTERFACES; CONTACT ION PAIRS; LIQUID-LIQUID EXTRACTION; OIL PHASE; ORGANIC PHASIS; TRI-N-BUTYL PHOSPHATE;

NITRIC ACID;

EID: 79952598581     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp111758s     Document Type: Article

References (90)

1. Perrier, C. Nature Lett. 1947, 159, 24
2. Musikas, C.; Schulz, W. W.; Liljenzin, J.-O. In Solvent Extraction Principles and Practices; Rydberg, J.; Musikas, C.; Chopin, G. R., Eds.; M. Dekker, Inc.: New York, 2004; p 527.
3. Leiser, K. H. Radiochim. Acta 1993, 63, 5
4. Holm, E. Radiochim. Acta 1993, 63, 57
5. Kubota, M. Radiochim. Acta 1993, 63, 91
6. Yoshihara, K.; Omori, T. Topics. Current. Chem.: Special Issue Devoted to the Chemistry of Technetium and Rhenium; Verlag Chemie: Berlin, 1996.
7. Boyd, G. E.; Larson, Q. V. J. Phys. Chem. 1960, 64, 988-996
8. Campbell, M. H. Anal. Chem. 1963, 35, 2052-2054
9. Mathur, J. N.; Murali, M. S.; Nash, K. L. Solvent Extr. Ion Exch. 2001, 19, 357-390
10. Schulz, W. W.; Navratil, J. D.; Kertes, A. S. Science and Technology of Tributyl Phosphate; CRC Press: Boca Raton, FL, 1984.
11. Jassim, T. N.; Liljenzin, J. O.; Lundqvist, R.; Persson, G. Solvent Extr. Ion Exch. 1984, 2, 404-419
12. Stephan, H.; Gloe, K.; Kraus, W.; Spies, H.; Johansen, B.; Wichman, K.; Reck, G.; Chand, D. K.; Bharadwaj, P. K.; Müller, U.; Müller, W. M.; Vögtle, F. In Fundamentals and Applications of Anion Separations; Moyer, B. A.; Singh, R. P., Eds.; Kluwer Academic Publishers: New York, 2004; pp 151 - 168.
13. Deutsch, E.; Libson, K.; Vanderheyden, J.-L. Technetium and Rhenium in Chemistry an Nuclear Medicine; Cortina International: Verona, Italy, 1989.
14. Katayev, E. A.; Kolesnikov, G. V.; Sessler, J. L. Chem. Soc. Rev. 2009, 38, 1572-1586
15. Korpusov, G. V.; Krylov, Y. S. Radiokhimiya 1984, 26, 408-410
16. Jalhoom, M. G. J. Radioanal. Nucl. Chem. Lett. 1986, 104, 131
17. Jalhoom, M. G. Radiochim. Acta 1986, 39, 195
18. Horwitz, E. P.; Dietz, M. L.; Fischer, D. E. Solvent Extr. Ion Exch. 1991, 9, 1-25
19. Zhou, Z.; Xing, Y.; Wu, Y. J. Inclusion Phenom. Macromol. Chem. 1999, 34, 219
20. Thuéry, P.; Nierlich, M.; Asfari, Z.; Vicens, J.; Dozol, J.-F. Polyhedron 2000, 19, 1749-1756
21. Schaekers, J. M. In Science and Technology of Tributyl Phosphate; Schulz, W. W.; Navratil, J. D.; Kertes, A. S., Eds.; CRC Press: Boston, 1991; Vol. IV, pp 71 - 122.
22. Naito, K.; Suzuki, T. J. Phys. Chem. 1962, 66, 983-988
23. Bucher, J. J.; Diamond, R. M. J. Chem. Phys. 1969, 73, 675-683
24. Kertes, A. S. J. Inorg. Nucl. Chem. 1960, 14, 104-113
25. Pruett, D. J. Sep. Sci. Technol. 1981, 16, 1157-1179
26. Pruett, D. J. Radiochim. Acta 1981, 29, 107-111
27. Kanellakopulos, B.; Konig, C. P. Radiochim. Acta 1983, 33, 169-175
28. Omori, T.; Tadokoro, M.; Suzuki, Y.; Suganuma, H.; Yoshihara, K. J. Radioanal. Nucl. Chem. 1994, 181, 71-76
29. El-Kot, A. M. J. Radioanal. Nucl. Chem. 1992, 163, 363-373
30. Pruett, D. J. Radiochim. Acta 1981, 29, 153-157
31. Kertes, A. S.; Beck, A. J. Chem. Soc. 1961, 1921
32. Macasek, F.; Kadrobova, J. Radioanal. Chem. 1979, 51, 97-106
33. Lieser, K. H.; Kruger, A.; Singh, R. N. Radiochim. Acta 1981, 28, 97-101
34. Chiarizia, R.; Briand, A.; Jensen, M. P.; Thiyagarajan, P. Solvent Extr. Ion Exch. 2008, 26, 333-359
35. Nave, S.; Mandin, C.; Martinet, L.; Berthon, L.; Testard, F.; Madic, C.; Zemb, T. Phys. Chem. Chem. Phys. 2004, 6, 799-808
36. Stoyanov, E. S. J. Chem. Soc., Faraday Trans. 1997, 93, 4165-4175
37. Osseo-Asare, K. Adv. Colloid Interface Sci. 1991, 37, 123-173
38. Allen, M. P.; Tildesley, D. J. Computer Simulation of Liquids.; Clarendon Press: Oxford, UK, 1987.
39. Beudaert, P.; Lamare, V.; Dozol, J.-F.; Troxler, L.; Wipff, G. Solvent Extr. Ion Exch. 1998, 16, 597-618
40. Baaden, M.; Berny, F.; Muzet, N.; Schurhammer, R.; Troxler, L.; Wipff, G. In Euradwaste 1999: Radioactive Waste management Strategies and Issues; Davies, C., Ed.; European Commission: Brussels, 2000; Vol. EUR 19143 EN, pp 519 - 522.
41. Baaden, M.; Burgard, M.; Wipff, G. J. Phys. Chem. B 2001, 105, 11131-11141
42. Baaden, M.; Berny, F.; Wipff, G. J. Mol. Liq. 2001, 90, 3-12
43. Baaden, M.; Schurhammer, R.; Wipff, G. J. Phys. Chem. B 2002, 106, 434-441
44. Schurhammer, R.; Wipff, G. In Separations and Processes Using Supercritical Carbon Dioxide; Gopalan, A. S.; Wai, C.; Jacobs, H., Eds.; American Chemical Society: Washington, DC, 2003; Vol. 860, Chapter 15, pp 223 - 244.
45. Schurhammer, R.; Wipff, G. J. Phys. Chem. A 2005, 109, 5208-5216
46. Jayasinghe, M.; Beck, T. L. J. Phys. Chem. B 2009, 113, 11662-11671
47. Case, D. A.; Pearlman, D. A.; Caldwell, J. W.; Cheatham, III, T. E.; Wang, J.; Ross, W. S.; Simmerling, C. L.; Darden, T. A.; Merz, K. M.; Stanton, R. V.; Cheng, A. L.; Vincent, J. J.; Crowley, M.; Tsui, V.; Gohlke, H.; Radmer, R. J.; Duan, Y.; Pitera, J.; Massova, I.; Seibel, G. L.; Singh, U. C.; Weiner, P. K.; Kollman, P. A. AMBER7, University of California: San Francisco, 2002.
48. Katayev, E. A.; Boev, N. V.; Khrustalev, V. N.; Ustynyuk, Y. A.; Tananaev, I. G.; Sessler, J. L. J. Org. Chem. 2007, 72, 2886-2877
49. Bridgeman, A. J.; Cavigliasso, G. Polyhedron 2001, 20, 2269-2277
50. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J. D.; Impey, R. W.; Klein, M. L. J. Chem. Phys. 1983, 79, 926-936
51. Jorgensen, W. L.; Tirado-Rives, J. J. Phys. Chem. 1996, 100, 14508-14515
52. Engler, E.; Wipff, G. In Crystallography of Supramolecular Compounds; Tsoucaris, G., Ed.; Kluwer: Dordrecht, The Netherlands, 1996; pp 471 - 476.
53. Kollman, P. Chem. Rev. 1993, 93, 2395-2417
54. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; M. A. Al-Laham; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.;; Pople, J. A. Gaussian 03 Revision B.05; Gaussian, Inc.: Pittsburgh, PA, 2003
55. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3093
56. No systematic conformational search was performed for TMP (taken in its gauche, gauche, trans form) and its adducts. The calculated energies are generally high enough, however, to estimate relative H-bonding interactions and acidities.
57. Experimentally, the proton affinity of alkylphosphates increases with the alkyl chain length, e.g., from trimethylphosphate TMP (211.5 kcal/mol) to triethylphosphate TEP (217.7 kcal/mol). See Lias, S. G.; Bartmess, J. E.; Liebman, J. F.;; Holmes, J. L.;; Levin, R. D.;; Mallard, W. G. J. Phys. Chem. Ref. Data 1998, 17.
58. Marcus, Y. The Properties of Solvents; John Wiley & Sons: Chichester, UK, 1998; Vol. 4.
59. 2O is 44.8 kcal/mol (see Lias, S. G.; Bartmess, J. E.; Liebman, J. F.;; Holmes, J. L.;; Levin, R. D.;; Mallard, W. G.; J. Phys. Chem. Ref. Data 1998, 17).
60. + to a single TBP molecule (-47.5 kcal/mol at the QM2 level).
61. 3H in the gas phase (by 19.9 and 16.9 kcal/mol, respectively) and in PCM-water (by 6.7 and 4.9 kcal/mol, respectively; see Table 2).
62. - series: -56.1, -57.1, and -59.6 kcal/mol at the QM1 level; -55.5, -56.3, and -57.9 kcal/mol, respectively at the QM2 level; -56.1, -57.0, and -58.5 kcal/mol, respectively, at the QM3 level.
63. + (see Table 4).
64. - interactions energies decrease in magnitude by ca. 50 kcal/mol from TBP to aqueous solutions (see Table S3).
65. - does: interaction energies are ca. -154 and -172 kcal/mol, respectively (see Table S3).
66. - (see Table 4 and Table S5 in the Supporting Information)).
67. VII:TBP ratio.
68. Whitney, D. C.; Diamond, R. M. J. Phys. Chem. 1963, 67, 209-216
69. Nakashima, T.; Lieser, K. H. Radiochim. Acta 1985, 203-206
70. Brownstein, S.; Stillman, A. E. J. Phys. Chem. 1959, 63, 2061-2062
71. Zhang, J.; Sun, Y.; Mao, C.; Gao, H.; Zhou, W.; Zhou, Z. J. Mol. Struct.: THEOCHEM 2009, 906, 46-49
72. Redlich, O.; Duerst, R. W.; Merbach, A. J. Chem. Phys. 1968, 49, 2986
73. See http://research.chem.psu.edu/brpgroup/Pka-compilation.pdf.
74. a's of different strong acids obtained by different methods
75. Schulz, W. W.; Navratil, J. D.; Kertes, A. S. Science and Technology of Tributyl Phosphate; CRC Press: Boca Raton, FL, 1991.
76. Stoyanov, E. S.; Mikhailov, V. A.; Chekmarev, A. M. Zh. Neorg. Khim. 1990, 35 (6) [English translation in Russ. J. Inorg. Chem. 1990 (1996)].
77. Stoyanov, E. S.; Mikhailov, V. A.; Chekmarev, A. M. Russ. J. Inorg. Chem. 1992, 37, 1323-1329
78. Naganawa, H.; Tachimori, S. Bull. Chem. Soc. Jpn. 1997, 70, 809-819
79. Stoyanov, E. S. Phys. Chem. Chem. Phys. 1999, 1, 2961-2966
80. Bürsing, H.; Ouw, D.; Kundu, S.; Vöhringer, P. Phys. Chem. Chem. Phys. 2001, 3, 2378-2387
81. Chiarizia, R.; Briand, A. Solvent Extr. Ion Ech. 2007, 25, 351-371
82. Antonio, M. R.; Chirizia, R.; Jaffrenou, F. Separation Sci. Technol. 2010, 45, 1689-1698
83. Erlinger, C.; Gazeau, D.; Zemb, T.; Madic, C.; Lefrançois, L.; Hebrant, M.; Tondre, C. Solvent Extr. Ion Exch. 1998, 16, 707-738
84. Moyer, B. A. In Molecular Recognition: Receptors for Cationic Guests; Atwood, J. L.; Davies, J. E. D.; McNicol, D. D.; Vögtle, F.; Lehn, J.-M., Eds.; Pergamon Elsevier: Oxford, UK, 1996; Vol. 1, Chapter 10, pp 377 - 416.
85. Junk, P. C. Rev. Inorg. Chem. 2001, 21, 93-124 and references cited therein
86. Meot-Ner, M.; Sieck, L. W. J. Phys. Chem. 1996, 100, 6445-6450
87. Bühl, M.; Ludwig, R.; Schurhammer, R; Wipff, G. J. Phys. Chem A 2004, 108, 11463-11468
88. Varnek, A.; Wipff, G.; Famulari, A.; Raimondi, M.; Stoyanov, E. J. Chem. Soc., Perkin Trans 2 2002, 887-893
89. Kebarle, P. Annu. Rev. Phys. Chem. 1977, 28, 445-476
90. + during the whole dynamics (Nicolas Sieffert, private communication).