Preferential solvation of organic species in binary solvent mixtures probed by intermolecular 1H NOESY NMR spectroscopy

Chemistry - A European Journal

Volumn 5, Issue 4, 1999, Pages 1291-1300

  Bagno, Alessandro ^a   Campulla, Marco ^a   Pirana, Matteo ^a   Scorrano, Gianfranco ^a   Stiz, Stefano ^a  

^a UNIVERSITY OF PADOVA   (Italy)

Author keywords

Binary solvent mixtures; Hydrophobic interactions; NMR spectroscopy; Nuclear Overhauser enhancement spectroscopy; Preferential solvation; Solvent effects

Indexed keywords

ORGANIC COMPOUND; SOLVENT;

ARTICLE; CHEMICAL REACTION; CIRCULAR DICHROISM; DRUG MIXTURE; HYDROPHOBICITY; IMAGE ENHANCEMENT; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; SOLVATION; SPECTROSCOPY;

EID: 0032946485     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990401)5:4<1291::AID-CHEM1291>3.0.CO;2-M     Document Type: Article

References (134)

1. a) A. Ben-Naim, J. Phys. Chem. 1989, 93, 3809;
2. b) A. Ben-Naim, Pure Appl. Chem. 1990, 62, 25.
3. K. S. Ennix, P. T. McMahon, R. de la Rosa, J. C Curtis, Inorg. Chem. 1987, 26, 2660.
4. a) M. J. Blandamer, J. Burgess, I. M. Horn, J. B. F. N. Engberts, P. Warrick, Coll. Surf. 1990, 48, 139;
5. b) M. J. Blandamer, J. Burgess, J. B. F. N. Engberts, P. Warrick, J. Mol. Liq. 1992, 52, 15;
6. c) C. H. Langford, J. P. K. Tong, J. Chem. Educ. 1977, 10, 258.
7. C. Treiner, A. Le Besnerais, C. Micheletti, Adv. Chem. Ser. 1979, 177, 109.
8. a) J. Komiyama, T. Mori, K. Yamamoto, T. Iijima, J. Chem. Soc. Faraday Trans. 1 1977, 73, 203;
9. b) I. Katime, C. Strazielle, Makromol. Chem. 1977, 178, 2295;
10. c) I. Katime, A. Campos, J. M. Tejon Rivera, Eur. Polym. J. 1979, 15, 291;
11. d) I. Katime, R. Valenciano, J. M. Tejon, Eur. Polym. J. 1979, 15, 261;
12. e) A. Dondos, I. Katime, C. Strazielle, Eur. Polym. J. 1983, 19, 579;
13. f) P. Kratochvil, D. Strakova, J. Stejskal, Z. Tuzar, Macromolecules 1983, 16, 1136;
14. g) I. A. Katime, J. R. Ochoa, J. M. Tejon, J. Chem. Soc. Faraday Trans. 2 1985, 81, 783;
15. h) M. R. Aven, C. Cohen, Makromol. Chem. 1988, 189, 881.
16. P. R. Wills, D. J. Winzor, Biopolymers 1993, 33, 1627.
17. M. Szpakowska, O. B. Nagy, J. Phys. Chem. 1989, 93, 3851.
18. a) D. Berek, T. Bleha, Z. Perna, J. Chromatogr. Sci. 1976, 14, 560;
19. b) R. E. Boehm, D. E. Martire, J. Phys. Chem. 1994, 98, 1317:
20. J. L. Wysocki, K. B. Sentell, Anal. Chem. 1998, 70, 602.
21. J. Grandjean, P. Laszlo, Pure Appl. Chem. 1993, 65, 2539.
22. H. Strehlow, H. H. Koepp, Z. Elektrochem. 1958, 62, 373.
23. a) A. Costigan, D. Feakins, I. McStravick, C. O'Duinn, J. Ryan, W. E. Waghorne, J. Chem. Soc. Faraday Trans. 1991, 87, 2443;
24. b) G. Carthy, D. Feakins, C. O'Duinn, W. E. Waghorne, J. Chem. Soc. Faraday Trans. 1991, 87, 2447;
25. M. Meade, K. Hickey, Y. McCarthy, W. E. Waghorne, M. R. Symons, P. P. Rastogi, J. Chem. Soc. Faraday Trans. 1997, 93, 563.
26. a) M. Szpakowska, O. B. Nagy, J. Chem. Soc. Faraday Trans. 1 1989, 85, 2891;
27. b) P. Chatterjee, S. Bagchi, J. Chem. Soc. Faraday Trans. 1991, 87, 587.
28. a) M. Rosés, C. Ràfols, J. Ortega, E. Bosch, J. Chem. Soc. Perkin Trans. 2 1995, 1607;
29. b) C. Ràfols, M. Rosés, E. Bosch. J. Chem. Soc. Perkin Trans. 2 1997, 243;
30. c) J. Barbosa, D. Barrón, R. Bergés, V. Sanz-Nebot, I. Toro, J. Chem. Soc. Faraday Trans. 1997, 93, 1915.
31. H. Boggetti, J. D. Anunziata, R. Cattana, J. J. Silber, Spectrochim. Acta Part A 1994, 50, 719.
32. a) W. P. Zurawsky, S. F. Scarlata, J. Phys. Chem. 1992, 96, 6012;
33. b) W. E. Acree, D. C. Wilkins, S. A. Tucker, J. M. Griffin, J. R. Powell, J. Phys. Chem. 1994, 98, 2537.
34. C. A. Khatri, Y. Pavlova, M. M. Green, H. Morawetz, J. Am. Chem. Soc. 1997, 119, 6991.
35. P. Chatterjee, S. Bagchi, J. Phys. Chem. 1991, 95, 3311.
36. D. Jamroz, J. Stangret, J. Lindgren, J. Am. Chem. Soc. 1993, 115, 6165.
37. J. E. Bertie, Z. Lan, J. Phys. Chem. 1997, 101, 4111.
38. a) G. Gonzales, N. Yutronic, Spectrochim. Acta Part A 1983, 39, 269;
39. b) H. Grahn, U. Edlund, T. A. Holak, Magn. Reson. Chem. 1987, 25, 497.
40. a) M. Holz, A. Sacco, M. Trotta, J. Solution Chem. 1990, 19, 193;
41. b) A. Sacco, M. C. Piccinni, M. Holz, J. Solution Chem. 1992, 21, 109.
42. S. Galera, J. M. Lluch, A. Oliva, J. Bertrand, J. Mol. Struct. 1988, 40, 101.
43. S. Galera, J. M. Lluch, A. Oliva, J. Bertrand, J. Chem. Soc. Faraday Trans. 1992, 88, 3537.
44. H. Kovacs, A. Laaksonen, J. Am. Chem. Soc. 1991, 113, 5596.
45. a) E. Hawlicka, D. Swiatla-Wojcik, Chem. Phys. 1995, 195, 221;
46. b) E. Hawlicka, D. Swiatla-Wojcik, Chem. Phys. 1997, 218, 49.
47. R. Gratias, H. Kessler, J. Phys. Chem. B 1998, 102, 2027.
48. a) A. K. Covington, K. E. Newman, Pure Appl. Chem. 1979, 51, 2041;
49. b) A. K. Covington, K. E. Newman, J. Chem. Soc. Faraday Trans. 1 1988, 84, 1393;
50. A. K. Covington, M. Dunn, J. Chem. Soc. Faraday Trans. 1 1989, 85, 2835.
51. K. Remerie, J. B. F. N. Engberts, J. Phys. Chem. 1983, 87, 5449.
52. a) O. B. Nagy, M. Muanda, J. B. Nagy, J. Chem. Soc. Faraday Trans. 1 1978, 74, 2210;
53. b) B. Parbhoo, O. B. Nagy, J. Chem. Soc. Faraday Trans. 1 1986, 82, 1789;
54. c) W. E. Acree Jr., A. I. Zvaigzne, S. A. Tucker, J. Chem. Soc. Faraday Trans. 1990, 86, 307.
55. a) Y. Marcus, Aust. J. Chem. 1983, 36, 1719;
56. b) Y. Marcus, J. Chem. Soc. Faraday Trans. 1 1988, 84, 1465;
57. Y. Marcus, J. Chem. Soc. Faraday Trans. 1 1989, 85, 381.
58. L. S. Frankel, T. R. Stengle, C. H. Langford, J. Phys. Chem. 1970, 74, 1376.
59. a) A. Ben-Naim, J. Chem. Phys. 1977, 67, 4884;
60. b) Fluctuation Theory of Mixtures, Vol. II (Eds.: E. Matteoli, G. Ali Mansoori), Taylor & Francis, New York, 1990;
61. K. E. Newman, Chem. Soc. Rev. 1994, 23, 31.
62. a) E. Matteoli, L. Lepori, J. Chem. Phys. 1984, 80, 2856;
63. b) E. Matteoli, L. Lepori, J. Chem. Soc. Faraday Trans. 1995, 91, 431;
64. E. Matteoli, J. Phys. Chem. B 1997, 101, 9800.
65. a) Y. Marcus, J. Chem. Soc. Faraday Trans. 1990, 86, 2215;
66. b) Y. Marcus, J. Chem. Soc. Faraday Trans. 1991, 87, 1843;
67. Y. Marcus, J. Chem. Soc. Faraday Trans. 1995, 91, 427.
68. a) M. J. Blandamer, N. J. Blundell, J. Burgess, H. J. Cowles, I. M. Horn, J. Chem. Soc. Faraday Trans. 1990, 86, 277;
69. b) M. J. Blandamer, N. J. Blundell, J. Burgess, H. J. Cowles, I. M. Horn, J. Chem. Soc. Faraday Trans. 1990, 86, 283;
70. c) M. J. Blandamer, J. Burgess, A. Cooney, H. J. Cowles, I. M. Horn, K. J. Martin, K. W. Morcom, P. Warrick, Jr., J. Chem. Soc. Faraday Trans. 1990, 86, 2209.
71. a) J. Zielkiewicz, J. Phys. Chem. 1995, 99, 4787;
72. b) J. Zielkiewicz, J. Chem. Soc. Faraday Trans. 1998, 94, 1713.
73. K. Nishikawa, Y. Kodera, T. Iijima, J. Phys. Chem. 1987, 91, 3694.
74. a) M. Holz, H. Weingärtner, H. G. Hertz, J. Chem. Soc. Faraday Trans. 1 1977, 73, 71;
75. b) J. Hála, Z. Phys. Chem. (Leipzig) 1983, 4, 749;
76. c) D. S. Gill, M. S. Chauhan, Z. Phys. Chem. (München) 1984, 140, 139;
77. d) K. Miyaji, K. Morinaga, Bull. Chem. Soc. Jpn. 1986, 59, 1695;
78. e) K. I. Hagen, C. M. Schwab, J. O. Edwards, D. A. Sweigart, Inorg. Chem. 1986, 25, 978;
79. f) K. Kobayashi, M. Yokoi, S. Kuroda, E. Kubota, Bull. Chem. Soc. Jpn. 1987, 60, 2535;
80. g) E. A. Gomaa, Bull. Soc. Chim. Fr. 1989, 623;
81. h) Y. Marcus, J. Chem. Soc. Dalton Trans. 1991, 2265;
82. i) A. Wakisaka, H. Sakuragi, K. Tokumaru, J. Chem. Soc. Faraday Trans. 1991, 87, 2167;
83. j) Y. Kondo, W. Sugitani, M. Tokui, J. Chem. Soc. Faraday Trans. 1992, 88, 3019;
84. k) D. S. Gill, B. Arona, K. C. Pathak, I. M. Joshi, M. S. Bakshi, J. Chem. Soc. Faraday Trans. 1992, 88, 57;
85. l)S. Alshehri, M. J. Blandamer, J. Burgess, P. Guardado, C. D. Hubbard, Polyhedron 1993, 12, 445;
86. C. Kalidas, G. Rajendran, Bull. Soc. Chim. Belg. 1993, 102, 5, 365;
87. n) M. Rosés, F. Rived, E. Bosch, J. Chem. Soc. Faraday Trans. 1993, 89, 1723;
88. o) B. Das, Bull. Chem. Soc. Jpn. 1994, 67, 1217;
89. p) A. Sacco, Chem. Soc. Rev. 1994, 23, 129.
90. a) M. Holz, R. Grunder, A. Sacco, A. Meleleo, J. Chem. Soc. Faraday Trans. 1993, 89, 1215;
91. b) A. Sacco, A. Asciolla, E. Matteoli, M. Holz, J. Chem. Soc. Faraday Trans. 1996, 92, 35;
92. A. Sacco, M. Holz, J. Chem. Soc. Faraday Trans. 1997, 93, 1101;
93. A. Sacco, F. M. De Cillis, M. Holz, J. Chem. Soc. Faraday Trans. 1998, 94, 2089.
94. a) C. Yu, G. C. Levy, J. Am. Chem. Soc. 1983, 105, 6994;
95. b) C. Yu, G. C. Levy, J. Am. Chem. Soc. 1984, 106, 6533.
96. P. L. Rinaldi, J. Am. Chem. Soc. 1983, 105, 5167.
97. a) W. Bauer, P. v. R. Schleyer, Magn. Reson. Chem. 1988, 26, 827;
98. b) W. Bauer, Magn. Reson. Chem. 1991, 29, 494.
99. a) H. B. Seba, B. Ancian, J. Magn. Reson. 1989, 84, 177;
100. b) H. B. Seba, B. Ancian, Chem. Commun. 1990, 996;
101. M. Chahinian, H. B. Seba, B. Ancian, Chem. Phys. Lett. 1998, 285, 337.
102. D. Canet, N. Mahieu, P. Tekely, J. Am. Chem. Soc. 1992, 114, 6190.
103. A. Wakisaka, S. Takahashi, N. Nishi, J. Chem. Soc. Faraday Trans. 1995, 91, 4063.
104. a) A. Wakisaka, Y. Yamamoto, Y. Akiyama, H. Takeo, F. Mizukami, K. Sakaguchi, J. Chem. Soc. Faraday Trans. 1996, 92, 3339;
105. b) A. Wakisaka, Y. Akiyama, Y. Yamamoto, T. Engst, H. Takeo, F. Mizukami, K. Sakaguchi, H. Jones, J. Chem. Soc. Faraday Trans. 1996, 92, 3539;
106. c) T. Koyama, A. Wakisaka, J. Chem. Soc. Faraday Trans. 1997, 93, 3813;
107. S. Mochizuki, Y. Usui, A. Wakisaka, J. Chem. Soc. Faraday Trans. 1998, 94, 547.
108. A. Bagno, G. Scorrano, S. Stiz, J. Am. Chem. Soc. 1997, 119, 2299.
109. a) J. H. Noggle, R. E. Schirmer, The Nuclear Overhauser Effect: Chemical Applications, Academic Press, New York, 1971;
110. b) D. Neuhaus, M. Williamson, The Nuclear Overhauser Effect in Structural and Conformational Analysis, VCH, Weinheim, 1989.
111. R. Kaiser, J. Chem. Phys. 1965, 42, 1838.
112. S. Macura, R. R. Ernst, Mol. Phys. 1980, 41, 95.
113. C. L. Perrin, T. J. Dwyer, Chem. Rev. 1990, 90, 935.
114. M. Holz, X. Mao, D. Seiferling, A. Sacco, J. Chem. Phys. 1996, 104, 669.
115. a) CRC Handbook of Chemistry and Physics, 77th ed., CRC, Boca Raton, 1996;
116. b) T. M. Aminabhavi, B. Gopalakrishna, J. Chem. Eng. Data 1995, 40, 856.
117. K. E. Kövér, G. Batta, J. Magn. Reson. 1986, 69, 344.
118. a) P. Bigler, C. Müller, J. Magn. Reson. 1988, 79, 45;
119. b) K. E. Kövér, G. Batta, J. Magn. Reson. 1988, 79, 206.
120. W. Bauer, Magn. Reson. Chem. 1996, 34, 532.
121. A. J. Parker, Chem. Rev. 1969, 69, 1.
122. I. Furó, P. Mutzenhardt, D. Canet, J. Am. Chem. Soc. 1995, 117, 10405.
123. a) K. J. Müller, H. G. Hertz, Chem. Scr. 1989, 29, 277;
124. b) K. J. Müller, H. G. Hertz, J. Phys. Chem. 1996, 100, 1256.
125. J. McConnell, The Theory of Nuclear Magnetic Relaxation in Liquids, Cambridge University Press, Cambridge, 1987.
126. J. Bromilow, J. L. M. Abboud, C. B. Lebrilla, R. W. Taft, G. Scorrano, V. Lucchini, J. Am. Chem. Soc. 1981, 103, 5448.
127. M. H. Abraham, Chem. Soc. Rev. 1993, 73.
128. a) E. M. Arnett, L. E. Small, D. Oancea, D. Johnston, J. Am. Chem. Soc. 1976, 98, 7346;
129. b) G. L. Perlovich, V. I. Smirnov, A. Ya. Fridman, Russ. J. Phys. Chem. (Engl. Transl.) 1991, 65, 1649.
130. W. Blokzijl, J. B. F. N. Engberts, Angew. Chem. 1993, 105, 1610; Angew. Chem. Int. Ed. Engl. 1993, 32, 1545.
131. W. Blokzijl, J. B. F. N. Engberts, Angew. Chem. 1993, 105, 1610; Angew. Chem. Int. Ed. Engl. 1993, 32, 1545.
132. A. Bagno, J. Chem. Soc. Faraday Trans. 1998, 94, 2501.
133. D. Ferro, V. Piacente, Thermochim. Acta 1985, 90, 387.
134. J. L. Finney, A. K. Soper, Chem. Soc. Rev. 1994, 23, 1.