Adsorption of ionophores and of their cation complexes at the water/chloroform interface: A molecular dynamics study of a [2.2.2]cryptand and of phosphoryl-containing podands

Chemistry - A European Journal

Volumn 3, Issue 4, 1997, Pages 552-560

  Varnek, A ^a   Troxler, L ^a   Wipff, G ^a  

^a UNIVERSITÉ LOUIS PASTEUR   (France)

Author keywords

counterion effect; extraction; interfaces; ionophores; molecular dynamics; solvation

Indexed keywords

EID: 0031003725     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030410     Document Type: Article

References (94)

1. P. R. Danesi in Principles and Practices of Solvent Extraction (Eds: J. Rydberg, C. Musikas, G. R. Choppin), Marcel Dekker, New York, 1992; pp. 157-208.
2. V. V. Tarasov, G. A. Yagodin, A. A. Pichugin, Kinetics of the Extraction of Inorganic Compounds (Russ), VINITI, Moscow, 1984, pp. 171. G. A. Yagodin, V. V. Tarasov, Solvent Extr. Ion Exch. 1984, 2, 139-179.
3. V. V. Tarasov, G. A. Yagodin, A. A. Pichugin, Kinetics of the Extraction of Inorganic Compounds (Russ), VINITI, Moscow, 1984, pp. 171. G. A. Yagodin, V. V. Tarasov, Solvent Extr. Ion Exch. 1984, 2, 139-179.
4. H. Watarai, Trends Anal. Chem. 1993, 12, 313-318.
5. a) V. V. Tarasov, A. V. Fomin, G. A. Yagodin, Zh. Physich, Khimii (Russ) 1971, 45, 1300.
6. b) N. H. Sagert, W. Lee, M. J. Quinn, Can. J. Chem. 1979, 57, 1218-1223.
7. G. F. Vandegrift, E. P. Horwitz, J. Inorg. Nucl. Chem. 1977, 39, 1425-1432.
8. N. K. Adam, Physics and Chemistry of Surfaces, 3rd ed., Oxford University Press, Oxford, 1941.
9. P. R. Danesi, R. Chiarizia, M. Pizzichini, A. Satelli, J. Inorg. Nucl. Chem. 1978, 40, 1119-1123.
10. V. V. Tarasov, G. A. Yagodin, Extraction Kinetics (Russ). VINITI, Moscow, 1974, pp. 119.
11. P. R. Danesi, R. Chiarizia, CRS Critical Reviews in Analytical Chemistry 1980, 10, 1-126. T. M. Fyles, J. Chem. soc. Farady Trans.1, 1986, 82, 617-633.
12. P. R. Danesi, R. Chiarizia, CRS Critical Reviews in Analytical Chemistry 1980, 10, 1-126. T. M. Fyles, J. Chem. soc. Farady Trans.1, 1986, 82, 617-633.
13. G. A. Yagodin, S. Z. Kagan, V. V. Tarasov, A. V. Ochkin, O. A. Sinegribova, V. V. Sergievsky, V. G. Vygon, Solvent Extraction (Russ), Khimiya, Moscow, 1981, pp. 399.
14. W. Lasek, W. Makosza, J. Phys. Org. Chem. 1993, 6, 412-420. C. M. Starks, C. L. Liotta, M. Halpern in Phase Transfer Catalysis (Ed.: C. M. Starks), Chapman & Hall, New York, 1994.
15. W. Lasek, W. Makosza, J. Phys. Org. Chem. 1993, 6, 412-420. C. M. Starks, C. L. Liotta, M. Halpern in Phase Transfer Catalysis (Ed.: C. M. Starks), Chapman & Hall, New York, 1994.
16. P. Vanysek, Electrochimica Acta 1995, 40, 2841-2847. W. Schmickler,Interfacial Electrochemistry, Oxford University Press, Oxford, 1996. H. H. J. Girault, D. J. Schriffin, Electroanalytical Chemistry (Ed.: A. J. Bard Dekker), New York, 1989. Spectrascopic and Diffraction Techniques in Interfacial Electrochemistry (Eds.: C. Gutierrez, C. Melendres), NATO ASI Series Vol. 320, Kluwer, Dordrecht, 1990. The Interface Structure and Electrochemical Processes at the Boundary between Two Immiscible Liquids (Ed.: V. E. Kazarinov), Berlin, 1987.
17. P. Vanysek, Electrochimica Acta 1995, 40, 2841-2847. W. Schmickler,Interfacial Electrochemistry, Oxford University Press, Oxford, 1996. H. H. J. Girault, D. J. Schriffin, Electroanalytical Chemistry (Ed.: A. J. Bard Dekker), New York, 1989. Spectrascopic and Diffraction Techniques in Interfacial Electrochemistry (Eds.: C. Gutierrez, C. Melendres), NATO ASI Series Vol. 320, Kluwer, Dordrecht, 1990. The Interface Structure and Electrochemical Processes at the Boundary between Two Immiscible Liquids (Ed.: V. E. Kazarinov), Berlin, 1987.
18. P. Vanysek, Electrochimica Acta 1995, 40, 2841-2847. W. Schmickler,Interfacial Electrochemistry, Oxford University Press, Oxford, 1996. H. H. J. Girault, D. J. Schriffin, Electroanalytical Chemistry (Ed.: A. J. Bard Dekker), New York, 1989. Spectrascopic and Diffraction Techniques in Interfacial Electrochemistry (Eds.: C. Gutierrez, C. Melendres), NATO ASI Series Vol. 320, Kluwer, Dordrecht, 1990. The Interface Structure and Electrochemical Processes at the Boundary between Two Immiscible Liquids (Ed.: V. E. Kazarinov), Berlin, 1987.
19. P. Vanysek, Electrochimica Acta 1995, 40, 2841-2847. W. Schmickler,Interfacial Electrochemistry, Oxford University Press, Oxford, 1996. H. H. J. Girault, D. J. Schriffin, Electroanalytical Chemistry (Ed.: A. J. Bard Dekker), New York, 1989. Spectrascopic and Diffraction Techniques in Interfacial Electrochemistry (Eds.: C. Gutierrez, C. Melendres), NATO ASI Series Vol. 320, Kluwer, Dordrecht, 1990. The Interface Structure and Electrochemical Processes at the Boundary between Two Immiscible Liquids (Ed.: V. E. Kazarinov), Berlin, 1987.
20. P. Vanysek, Electrochimica Acta 1995, 40, 2841-2847. W. Schmickler,Interfacial Electrochemistry, Oxford University Press, Oxford, 1996. H. H. J. Girault, D. J. Schriffin, Electroanalytical Chemistry (Ed.: A. J. Bard Dekker), New York, 1989. Spectrascopic and Diffraction Techniques in Interfacial Electrochemistry (Eds.: C. Gutierrez, C. Melendres), NATO ASI Series Vol. 320, Kluwer, Dordrecht, 1990. The Interface Structure and Electrochemical Processes at the Boundary between Two Immiscible Liquids (Ed.: V. E. Kazarinov), Berlin, 1987.
21. A. Adamson, Physical Chemistry of Surfaces, Wiley Interscience, New York, 1990; see also P. C. Hiemenz, Principles of Colloid and Surface Chemistry, 2nd ed., M. Dekker, New York, 1986.
22. A. Adamson, Physical Chemistry of Surfaces, Wiley Interscience, New York, 1990; see also P. C. Hiemenz, Principles of Colloid and Surface Chemistry, 2nd ed., M. Dekker, New York, 1986.
23. R. R. Naujok, H. J. Paul, R. M. Corn, J. Phys. Chem. 1996, 100, 10497-10507.
24. T. Takenaka, T. Nakagana, J. Phys. Chem. 1976, 80, 475-480. R. P. Sperline, H. Freiser, Langmuir 1990, 6, 334.
25. T. Takenaka, T. Nakagana, J. Phys. Chem. 1976, 80, 475-480. R. P. Sperline, H. Freiser, Langmuir 1990, 6, 334.
26. P. Linse, J. Chem. Phys. 1987, 86, 4177-4187.
27. J. Gao, W. L. Jorgensen, J. Phys. Chem. 1988, 92, 5813-5822.
28. I. L. Carpenter, W. J. Hehre, J. Phys. Chem. 1990, 94, 531-536.
29. D. Michael, I. Benjamin, J. Phys. Chem. 1995, 99, 1530-1536.
30. A. R. van Buuren, S.-J. Marrink, H. J. C. Berendsen, J. Phys. Chem. 1993, 97, 9206-9212.
31. M. A. Wilson, A. Pohorille, J. Am. Chem. Soc. 1994, 116, 1490-1501. See also B. Smit, Phys. Rev. A, 1988, 37, 3431. K. Esselink, P. A. J. Hilbers, S. Karaborni, J. L. Siepmann, B. Smit, Molecular Simulation, 1995, 14, 259-274 and references therein.
32. M. A. Wilson, A. Pohorille, J. Am. Chem. Soc. 1994, 116, 1490-1501. See also B. Smit, Phys. Rev. A, 1988, 37, 3431. K. Esselink, P. A. J. Hilbers, S. Karaborni, J. L. Siepmann, B. Smit, Molecular Simulation, 1995, 14, 259-274 and references therein.
33. M. A. Wilson, A. Pohorille, J. Am. Chem. Soc. 1994, 116, 1490-1501. See also B. Smit, Phys. Rev. A, 1988, 37, 3431. K. Esselink, P. A. J. Hilbers, S. Karaborni, J. L. Siepmann, B. Smit, Molecular Simulation, 1995, 14, 259-274 and references therein.
34. C. Y. Lee, J. A. McCammon, P. J. Rossky, J. Chem. Phys. 1984, 80, 4448-4455.
35. W. Guba, H. Kessler, J. Phys. Chem. 1994, 98, 23-27. See also W. Guba, R. Haessner, G. Breipohl, S. Henke, J. Knolle, V. Santagada, H. Kessler, J. Am. Chem. Soc. 1994, 116, 7532-7540.
36. W. Guba, H. Kessler, J. Phys. Chem. 1994, 98, 23-27. See also W. Guba, R. Haessner, G. Breipohl, S. Henke, J. Knolle, V. Santagada, H. Kessler, J. Am. Chem. Soc. 1994, 116, 7532-7540.
37. K. J. Schweighofer, I. Benjamin, J. Phys. Chem. 1995, 99, 9974-9985. I. Benjamin, Science. 1993, 261, 1558-1560.
38. K. J. Schweighofer, I. Benjamin, J. Phys. Chem. 1995, 99, 9974-9985. I. Benjamin, Science. 1993, 261, 1558-1560.
39. A. Varnek, G. Wipff, J. Comput. Chem. 1996, 17, 1520-1531.
40. A. Varnek, C. Sirlin, G. Wipff, in Crystallography of Supramolecular Compounds (Ed.: G. Tsoucaris), NATO ASI Series Vol. C480, Dordrecht, 1996, pp. 67-99.
41. M. Lauterbach, G. Wipff, Supramol. Chem. 1995, 6, 187-207.
42. + Binding Selectivity. A MD FEP Study in Pure Chloroform and MD Simulations at the Water/ Chloroform Interface in Physical Supramolecular Chemistry (Ed.: L. Echegoyen), NATO ASI Series, Kluwer, Dordrecht, 1996, pp. 65-102.
43. G. Wipff, E. Engler, P. Guilbaud, M. Lauterbach, L. Troxler, A. Varnek, New. J. Chem. 1996, 20, 403-417.
44. I. Benjamin, J. Chem. Phys. 1992, 97, 1432-1445 and 1992, 96, 577-585.
45. I. Benjamin, J. Chem. Phys. 1992, 97, 1432-1445 and 1992, 96, 577-585.
46. P. Guilbaud, G. Wipff, New J. Chem. 1996, 20, 631-642.
47. B. Dietrich, P. Viout, J.-M. Lehn, Macrocyclic Chemistry, VCH, Weinheim, 1993, pp. 371. J.-P. Behr, M. Kirch, J.-M. Lehn, J. Am. Chem. Soc. 1985, 107, 241-246.
48. B. Dietrich, P. Viout, J.-M. Lehn, Macrocyclic Chemistry, VCH, Weinheim, 1993, pp. 371. J.-P. Behr, M. Kirch, J.-M. Lehn, J. Am. Chem. Soc. 1985, 107, 241-246.
49. P. Auffinger, G. Wipff, J. Am. Chem. Soc. 1991, 113, 5976-5988. P. Auffinger and G. Wipff, J. Chimie Phys. 1991, 88, 2525-2534.
50. P. Auffinger, G. Wipff, J. Am. Chem. Soc. 1991, 113, 5976-5988. P. Auffinger and G. Wipff, J. Chimie Phys. 1991, 88, 2525-2534.
51. L. Troxler, G. Wipff, J. Am. Chem. Soc. 1994, 116, 1468-1480. G. Wipff, L. Troxler in Computational Approaches in Supramolecular Chemistry (Ed.: G. Wipff), NATO ASI Series Vol. C426, Kluwer, Dordrecht, 1994, pp. 319-348.
52. L. Troxler, G. Wipff, J. Am. Chem. Soc. 1994, 116, 1468-1480. G. Wipff, L. Troxler in Computational Approaches in Supramolecular Chemistry (Ed.: G. Wipff), NATO ASI Series Vol. C426, Kluwer, Dordrecht, 1994, pp. 319-348.
53. J. Åqvist, J. Phys. Chem. 1990, 94, 8021-8024.
54. V. Baulin, V. Soloviev, A. Varnek, G. Wipff, unpublished results. Concerning the nomenclature, MP can be considered either as a monopodand or as a dipodand. The latter description applies when the central ether oxygen acts as an anchoring group, which may not be the case here (E. Weber and F. Vögtle, Crown-Type Compounds - An Introductory Overview in Host-Guest Complex Chemistry I, Topics Current Chemistry, Springer, Berlin, 1981, p. 3.
55. V. Baulin, V. Soloviev, A. Varnek, G. Wipff, unpublished results. Concerning the nomenclature, MP can be considered either as a monopodand or as a dipodand. The latter description applies when the central ether oxygen acts as an anchoring group, which may not be the case here (E. Weber and F. Vögtle, Crown-Type Compounds - An Introductory Overview in Host-Guest Complex Chemistry I, Topics Current Chemistry, Springer, Berlin, 1981, p. 3.
56. L. Cecille, M. Casarci, L. Pietrelli, New Separation Chemistry Techniques for Radioactive Waste and other Specific Applications, Elsevier, London, 1991.
57. A. Y. Nazarenko, A. Varnek, G. Wipff, unpublished results.
58. A. Varnek, G. Morosi, A. Gamba, J. Phys. Org. Chem. 1992, 5, 109-118.
59. D. A. Pearlman, D. A. Case, J. C. Cadwell, G. L. Seibel, U. C. Singh, P. Weiner, P. A. Kollman, AMBER4, University of California, San Francisco, 1991.
60. S. J. Weiner, P. A. Kollman, D. A. Case, U. C. Singh, C. Ghio, G. Alagona, S. Profeta, Jr., P. Weiner, J. Am. Chem. Soc. 1984, 106, 765. S. J. Weiner, P. A. Kollman, D. T. Nguen, D. A. Case, J. Comput. Chem. 1986, 7, 230.
61. S. J. Weiner, P. A. Kollman, D. A. Case, U. C. Singh, C. Ghio, G. Alagona, S. Profeta, Jr., P. Weiner, J. Am. Chem. Soc. 1984, 106, 765. S. J. Weiner, P. A. Kollman, D. T. Nguen, D. A. Case, J. Comput. Chem. 1986, 7, 230.
62. SPARTAN, Version 4.0.4, Wavefunction 1995.
63. W. L. Jorgensen, J. Chandrasekhar, J. D. Madura, J. Chem. Phys. 1983, 79, 926-935.
64. W. L. Jorgensen, J. M. Briggs, M. L. Contreras, J. Phys. Chem. 1990, 94, 1683-1686.
65. E. Engler, G. Wipff, G. MD-DRAW. A Program for Graphical Representation of a Molecular Trajectories, Université Louis Pasteur, Strasbourg, 1992. See Crystallography of Supramolecular Compounds (Ed.: G. Tsoucaris), NATO ASI Series Vol. C480, Kluwer, Dordrecht, 1996, pp. 461-476. E. Engler, G. Wipff, MDS. A Program to Analyze MD Trajectories, unpublished.
66. E. Engler, G. Wipff, G. MD-DRAW. A Program for Graphical Representation of a Molecular Trajectories, Université Louis Pasteur, Strasbourg, 1992. See Crystallography of Supramolecular Compounds (Ed.: G. Tsoucaris), NATO ASI Series Vol. C480, Kluwer, Dordrecht, 1996, pp. 461-476. E. Engler, G. Wipff, MDS. A Program to Analyze MD Trajectories, unpublished.
67. E. Engler, G. Wipff, G. MD-DRAW. A Program for Graphical Representation of a Molecular Trajectories, Université Louis Pasteur, Strasbourg, 1992. See Crystallography of Supramolecular Compounds (Ed.: G. Tsoucaris), NATO ASI Series Vol. C480, Kluwer, Dordrecht, 1996, pp. 461-476. E. Engler, G. Wipff, MDS. A Program to Analyze MD Trajectories, unpublished.
68. M. Carlà, C. M. C. Gambi, P. Baglioni, J. Phys. Chem. 1996, 100, 11067-11071.
69. B. Guillot, Y. Guissani, S. Bratos, J. Chem. Phys. 1991, 95, 3643. A. Wallqvist, J. Phys. Chem. 1991, 95, 8921-8927. W. Blokzijl, J. B. F. N. Engberts, Angew. Chem. Int. Ed. Engl. 1993, 32, 1545. A. Pohorille, L. R. Pratt, J. Am. Chem. Soc. 1990, 112, 5066-5074. R. A. Pierotti, Chem. Rev. 1976, 76, 717-726. M. Prevost, I. T. Oliveira, J.-P. Kocher, S. J. Wodak, J. Phys. Chem. 1996, 100, 2738-2743 and references therein.
70. B. Guillot, Y. Guissani, S. Bratos, J. Chem. Phys. 1991, 95, 3643. A. Wallqvist, J. Phys. Chem. 1991, 95, 8921-8927. W. Blokzijl, J. B. F. N. Engberts, Angew. Chem. Int. Ed. Engl. 1993, 32, 1545. A. Pohorille, L. R. Pratt, J. Am. Chem. Soc. 1990, 112, 5066-5074. R. A. Pierotti, Chem. Rev. 1976, 76, 717-726. M. Prevost, I. T. Oliveira, J.-P. Kocher, S. J. Wodak, J. Phys. Chem. 1996, 100, 2738-2743 and references therein.
71. B. Guillot, Y. Guissani, S. Bratos, J. Chem. Phys. 1991, 95, 3643. A. Wallqvist, J. Phys. Chem. 1991, 95, 8921-8927. W. Blokzijl, J. B. F. N. Engberts, Angew. Chem. Int. Ed. Engl. 1993, 32, 1545. A. Pohorille, L. R. Pratt, J. Am. Chem. Soc. 1990, 112, 5066-5074. R. A. Pierotti, Chem. Rev. 1976, 76, 717-726. M. Prevost, I. T. Oliveira, J.-P. Kocher, S. J. Wodak, J. Phys. Chem. 1996, 100, 2738-2743 and references therein.
72. B. Guillot, Y. Guissani, S. Bratos, J. Chem. Phys. 1991, 95, 3643. A. Wallqvist, J. Phys. Chem. 1991, 95, 8921-8927. W. Blokzijl, J. B. F. N. Engberts, Angew. Chem. Int. Ed. Engl. 1993, 32, 1545. A. Pohorille, L. R. Pratt, J. Am. Chem. Soc. 1990, 112, 5066-5074. R. A. Pierotti, Chem. Rev. 1976, 76, 717-726. M. Prevost, I. T. Oliveira, J.-P. Kocher, S. J. Wodak, J. Phys. Chem. 1996, 100, 2738-2743 and references therein.
73. B. Guillot, Y. Guissani, S. Bratos, J. Chem. Phys. 1991, 95, 3643. A. Wallqvist, J. Phys. Chem. 1991, 95, 8921-8927. W. Blokzijl, J. B. F. N. Engberts, Angew. Chem. Int. Ed. Engl. 1993, 32, 1545. A. Pohorille, L. R. Pratt, J. Am. Chem. Soc. 1990, 112, 5066-5074. R. A. Pierotti, Chem. Rev. 1976, 76, 717-726. M. Prevost, I. T. Oliveira, J.-P. Kocher, S. J. Wodak, J. Phys. Chem. 1996, 100, 2738-2743 and references therein.
74. B. Guillot, Y. Guissani, S. Bratos, J. Chem. Phys. 1991, 95, 3643. A. Wallqvist, J. Phys. Chem. 1991, 95, 8921-8927. W. Blokzijl, J. B. F. N. Engberts, Angew. Chem. Int. Ed. Engl. 1993, 32, 1545. A. Pohorille, L. R. Pratt, J. Am. Chem. Soc. 1990, 112, 5066-5074. R. A. Pierotti, Chem. Rev. 1976, 76, 717-726. M. Prevost, I. T. Oliveira, J.-P. Kocher, S. J. Wodak, J. Phys. Chem. 1996, 100, 2738-2743 and references therein.
75. R. Avayard, B. Vincent, Prog. Surf. Sci. 1977, 8, 59. R. Aveyard, R. W. Mitchell, Trans. Farad. Soc. 1969, 65, 2645-2653.
76. R. Avayard, B. Vincent, Prog. Surf. Sci. 1977, 8, 59. R. Aveyard, R. W. Mitchell, Trans. Farad. Soc. 1969, 65, 2645-2653.
77. P. Beudaert, G. Wipff, unpublished results.
78. R. C. Weast, CRC Handbook of Chemistry and Physics, CRC Press, Cranwood Parkway, Cleveland, 1978.
79. X. Daura, P. H. Hünenberger, A. E. Mark, E. Querol, F. X. Avilés, W. F. van Gunsteren, J. Am. Chem. Soc. 1996, 118, 6285-6294.
80. C. Wei, A. J. Bard, M. V. Mirkin, J. Phys. Chem. 1995, 99, 16033-16042.
81. R.-S. Tsai, W. Fan, N. E. Tayar, P.-A. Carrupt, B. Testa, L. B. Kier, J. Am. Chem. Soc. 1993, 115, 9632-9639. W. Fan, R.-S. Tsai, N. E. Tayar, P.-A. Carrupt, B. Testa, J. Phys. Chem. 1994, 98, 329-333.
82. R.-S. Tsai, W. Fan, N. E. Tayar, P.-A. Carrupt, B. Testa, L. B. Kier, J. Am. Chem. Soc. 1993, 115, 9632-9639. W. Fan, R.-S. Tsai, N. E. Tayar, P.-A. Carrupt, B. Testa, J. Phys. Chem. 1994, 98, 329-333.
83. J. Tomasi, M. Persico, Chem. Rev. 1994, 94, 2027-2094 and references therein.
84. H. Watarai, Y. Shibuya, Y. Bull. Chem. Soc. Jpn. 1989, 62, 3446-3450.
85. L. Giovannino, G. Wipff, unpublished results.
86. M. Ioshio, H. Noguchi, K. Inoue, in Proc. Int. Solv. Extr. Conf. (ISEC-83), Denver, Colorado, USA, 1983, pp. 309-310.
87. M. Lauterbach, G. Wipff, unpublished results. M. Lauterbach, Simulation par ordinateur de l'extraction liquide-liquide des cations alcalins par des ionophores de type calixarène-couronne et valinomycine, PhD Thesis, Université Louis Pasteur de Strasbourg, 1996.
88. M. Lauterbach, G. Wipff, unpublished results. M. Lauterbach, Simulation par ordinateur de l'extraction liquide-liquide des cations alcalins par des ionophores de type calixarène-couronne et valinomycine, PhD Thesis, Université Louis Pasteur de Strasbourg, 1996.
89. L. Troxler and G. Wipff, MD Simulations of Ionophores Free and Complexed at a Water-Chloroform Interface, poster presented at the XXI International Symposium on Macrocyclic Chemistry, 1996, Montecatini, Italy.
90. K. Monserrat, M. Graètzel, P. Tundo, J. Am. Chem. Soc. 1980, 102, 5527-5529. Y. C. Liu, P. Baglioni, J. Teixeira, S. H. Chen, J. Phys. Chem. 1994, 98, 10208-10215, and references therein.
91. K. Monserrat, M. Graètzel, P. Tundo, J. Am. Chem. Soc. 1980, 102, 5527-5529. Y. C. Liu, P. Baglioni, J. Teixeira, S. H. Chen, J. Phys. Chem. 1994, 98, 10208-10215, and references therein.
92. B. H. Honig, W. L. Hubbel, R. F. Flewelling, Annu. Rev. Biophys. Biophys. Chem. 1986, 15, 163. R. B. Gennis, Biomembranes, Springer, New York, 1989. Y. Shao, H. H. Girault, J. Electroanal. Chem. 1990, 282, 59.
93. B. H. Honig, W. L. Hubbel, R. F. Flewelling, Annu. Rev. Biophys. Biophys. Chem. 1986, 15, 163. R. B. Gennis, Biomembranes, Springer, New York, 1989. Y. Shao, H. H. Girault, J. Electroanal. Chem. 1990, 282, 59.
94. B. H. Honig, W. L. Hubbel, R. F. Flewelling, Annu. Rev. Biophys. Biophys. Chem. 1986, 15, 163. R. B. Gennis, Biomembranes, Springer, New York, 1989. Y. Shao, H. H. Girault, J. Electroanal. Chem. 1990, 282, 59.