Hydrophobic interactions and chemical reactivity

Organic and Biomolecular Chemistry

Volumn 1, Issue 16, 2003, Pages 2809-2820

  Otto, Sijbren ^a   Engberts, Jan B F N ^b  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; DISSOLUTION; ENTHALPY; GIBBS FREE ENERGY; HYDRATION; HYDROGEN BONDS; MOLECULES; PHOSPHOLIPIDS; THERMODYNAMICS;

APOLAR MOLECULES; HYDROPHOBIC HYDRATION; NONCOVALENT INTERACTIONS;

HYDROPHOBICITY;

EID: 0041818406     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b305672d     Document Type: Article

References (101)

1. W. Blokzijl and J. B. F. N. Engberts, Angew. Chem., Int. Ed. Engl., 1993, 32, 1545 (Angew. Chem., 1993, 105, 1610)
2. (b) N. T. Southall, K. A. Dill and A. D. Haymet, J. Phys. Chem. B, 2002, 106, 521
3. (c) L. R. Pratt and A. Pohorille, Chem. Rev., 2002, 102, 2671
4. (d) R. Schmid, Monatsh. Chem., 2001, 132, 1295.
5. (a) H. S. Frank and M. W. Evans, J. Chem. Phys., 1945, 13, 507
6. (b) M. H. Abraham, J. Am. Chem. Soc., 1982, 104, 2085.
7. G. Graziano, J. Chem. Soc., Faraday Trans., 1998, 94, 3345.
8. V. V. Yaminsky and E. A. Vogler, Curr. Opinion Coll. Interf. Sci., 2001, 6, 342.
9. J. R. Haak and J. B. F. N. Engberts, J. Am. Chem. Soc., 1986, 108, 1705.
10. Y.-K. Cheng and P. J. Rossky, Nature, 1998, 392, 696.
11. M. J. Blandamer, J. B. F. N. Engberts, manuscript in preparation.
12. (a) J. B. F. N. Engberts and M. J. Blandamer, J. Phys. Org. Chem., 1998, 11, 841
13. (b) J. B. F. N. Engberts and M. J. Blandamer, Chem. Commun., 2001, 1701
14. (c) M. J. Blandamer, J. Burges, J. B. F. N. Engberts and F. Sanchez, Faraday Discuss., 1988, 85, 309.
15. M. J. Blandamer, J. Burgess, H. J. Cowles, A. J. de Young, J. B. F. N. Engberts, S. A. Galema, S. J. Hill and I. M. Horn, J. Chem. Soc., Chem. Commun., 1988, 1141.
16. (a) T. H. Fife and D. M. McMahon, J. Am. Chem. Soc., 1969, 91, 7481
17. (b) J. F. J. Engbersen and J. B. F. N. Engberts, J. Am. Chem. Soc., 1975, 97, 1563
18. (c) W. Karzijn and J. B. F. N. Engberts, Tetrahedron Lett., 1978, 1787.
19. (a) M. F. Lensink, J. Mavri and H. J. C. Berendsen, J. Comput. Chem., 1999, 886
20. (b) T. Rispens, M. F. Lensink, H. J. C. Berendsen and J. B. F. N. Engberts, J. Phys. Chem. B, to be submitted.
21. (a) W. Blokzijl, J. B. F. N. Engberts and M. J. Blandamer, J. Am. Chem. Soc., 1990, 112, 1197
22. (b) H. Benak, J. B. F. N. Engberts and M. J. Blandamer, J. Chem. Soc., Perkin Trans. 2, 1992, 2035.
23. W. Blokzijl, J. B. F. N. Engberts, J. Jager and M. J. Blandamer, J. Phys. Chem., 1987, 91, 6022.
24. (a) N. J. Buurma, L. Pastorello, M. J. Blandamer and J. B. F. N. Engberts, J. Am. Chem. Soc., 2001, 123, 11848
25. (b) N. B. Buurma, Ph.D. Thesis, University of Groningen, The Netetherlands, 2003.
26. (a) J. B. F. N. Engberts, Water Compr. Treatise, 1972-1982, 1979, 6, ch. 4
27. (b) R. Lumry and S. Rajender, Biopolymers, 1970, 9, 1125.
28. For a detailed study of the hydration thermodynamics of aliphatic alcohols, see: G. Graziano, Phys. Chem. Chem. Phys., 1999, 1, 3567.
29. (a) W. H. Noordman, W. Blokzijl, J. B. F. N. Engberts and M. J. Blandamer, J. Org. Chem., 1993, 58, 7111
30. (b) P. Hol, L. Streefland, M. J. Blandamer and J. B. F. N. Engberts, J. Chem. Soc., Perkin Trans. 1997, 485.
31. J. J. Savage and R. H. Wood, J. Solution Chem., 1976, 10, 733.
32. G. Graziano and G. Barone, J. Am. Chem. Soc., 1996, 118, 1831.
33. (a) S. A. Galema, M. J. Blandamer and J. B. F. N. Engberts, J. Org. Chem., 1992, 57, 1995
34. (b) For a supporting MD simulation, see: S. A. Galema, E. Howard, J. B. F. N. Engberts and J. R. Grigera, Carbohydr. Res., 1994, 265, 215.
35. (a) A. Lubineau, J. Auge and Y. Queneau, Synthesis, 1994, 741
36. (b) C. Li, Chem. Rev., 1993, 2023
37. (c) J.B.F.N. Engberts, B.L. Feringa, E. Keller and S. Otto, Recl. Trav. Chim. Pays-Bas, 1996, 115, 457
38. (d) C. Li and T.-H. Chan, Organic Reactions in Aqueous Media, Wiley, New York, 1997
39. (e) P. A. Grieco, Organic Synthesis in Water, Blacky Academic and Professional, London, 1998
40. (f) K. Manabe and S. Kobayashi, Chem. Eur. J., 2002, 8, 4095
41. (g) U. M. Lindström, Chem. Rev., 2002, 102, 2751.
42. For a review on Diels-Alder reactions in water see: S. Otto and J. B. F. N. Engberts, Pure Appl. Chem., 2000, 72, 1365.
43. R. Breslow and D. Rideout, J. Am. Chem. Soc., 1980, 102, 7816.
44. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 2nd ed., VCH, Weinheim, 1988.
45. G. Desimoni, G. Faita, P. P. Righetti and L. Toma, Tetrahedron, 1990, 46, 7951.
46. J. W. Wijnen and J. B. F. N. Engberts, Liebigs Ann./Recl., 1997, 1085.
47. W. Blokzijl, Ph. D. Thesis, University of Groningen, The Netherlands, 1991.
48. A. Meijer, S. Otto and J. B. F. N. Engberts, J. Org. Chem., 1998, 63, 8989.
49. I. Hunt and C. D. Johnson, J. Chem. Soc., Perkin Trans. 2, 1991, 1051.
50. A. Lubineau, H. Bienaymé, Y. Queneau and M. Scherrmann, New J. Chem., 1994, 18, 279.
51. (a) J. F. Blake and W. L. Jorgensen, J. Am. Chem. Soc., 1991, 113, 7430
52. (b) J. F. Blake, L. D. Lim and W. L. Jorgensen, J. Org. Chem., 1994, 59, 803
53. (c) T. R. Furlani and J. Gao, J. Org. Chem., 1996, 61, 5492
54. (d) Y. Pak and G. A. Voth, J. Phys. Chem. A, 1999, 103, 925
55. (e) Y. Harano, H. Sato and F. Hirata, Chem. Phys., 2000, 258, 151
56. (f) S. Kong and J. D. Evanseck, J. Am. Chem. Soc., 2000, 122, 10418
57. (g) J. Chandrasekhar, S. Shariffskul and W. L. Jorgensen, J. Phys. Chem. B., 2002, 106, 8078.
58. D. van Mersbergen, J. W. Wijnen and J. B. F. N. Engberts, J. Org. Chem., 1998, 63, 8801.
59. K. J. Dignam, A. F. Hegarty and P. L Quain, J. Org. Chem., 1978, 43, 388.
60. Y. Inoue, K. Araki and S. Shiraishi, Bull. Chem. Soc. Jpn., 1991, 64, 3079.
61. (a) M. R. Gholami and A. H. Yangjeh, J. Chem. Res. Synop., 1999, 226
62. (b) M. R. Gholami and A. H. Yangjeh, Int. J. Chem. Kinet., 2000, 32, 431.
63. M. P. Repasky and W. L. Jorgensen, Faraday Discuss., 1998, 110, 379.
64. (a) B. Ganem, Angew. Chem., Int. Ed. Engl., 1996, 35, 937 (Angew. Chem., 1996, 108, 1014)
65. (b) J. J. Gajewski, Acc. Chem. Res., 1997, 30, 219.
66. E. Brandes, P. A. Grieco and J. J. Gajewski, J. Org. Chem., 1989, 54, 515.
67. J. J. Gajewski, J. Org. Chem., 1992, 57, 5500.
68. (a) S. Otto, W. Blokzijl and J. B. F. N. Engberts, J. Org. Chem., 1994, 59, 5372
69. (b) J. B. F. N. Engberts, Pure Appl. Chem., 1995, 67, 823.
70. (a) D. L. Severance and W. L. Jorgensen, J. Am. Chem. Soc., 1992, 114, 10966
71. (b) C. J. Cramer and D. G. Truhlar, J. Am. Chem. Soc., 1992, 114, 8794
72. (c) J. Gao, J. Am. Chem. Soc., 1994, 116, 1563
73. (d) M. M. Davidson, I. H. Hillier, R. J. Hall and N. A. Burton, J. Am. Chem. Soc., 1994, 116, 9294
74. M. M. Davidson and I. H. Hillier, J. Phys. Chem., 1995, 99, 6748
75. A. Sehgal, L. Shao and J. L. Gao, J. Am. Chem. Soc., 1995, 117, 11337
76. (f) J. M. Guest, J. S. Craw, M. A. Vincent and I. H. Hillier, J. Chem. Soc., Perkin Trans. 2, 1997, 71.
77. M. H. Abraham, P. L. Grellier, A. Nasehzadeh and R. A. C. Walker, J. Chem. Soc., Perkin Trans. 2, 2, 1988, 1717.
78. (a) A. Lubineau, J. Org. Chem., 1986, 51, 2142
79. (b) A. Lubineau and E. Meyer, Tetrahedron, 1988, 44, 6065.
80. T.-P. Loh, L.-C. Feng and L.-L. Wei, Tetrahedron, 2000, 56, 7309.
81. H. Yorimitsu, T. Nakamura, H. Shinokubo, K. Oshima, K. Omoto and H. Fujimoto, J. Am. Chem. Soc., 2000, 122, 11041.
82. X.-K. Jiang, W.-Q. Fan and Y.Z. Hui, J. Am. Chem. Soc., 1984, 106, 7202.
83. X.-K. Jiang, Y.-Z. Hui and Z.-X. Fei, J. Chem. Soc., Chem. Commun., 1988, 689.
84. W.-Q. Fan and X.-K. Jiang, J. Am. Chem. Soc., 1985, 107, 7680.
85. R. Breslow, Acc. Chem. Res., 1991, 24, 159.
86. (a) E. T. Kool and R. Breslow, J. Am. Chem. Soc., 1988, 110, 1596
87. (b) R. Breslow and R. V. Conners, J. Am. Chem. Soc., 1995, 117, 6601.
88. (a) R. Breslow and Z. N. Zhu, J. Am. Chem. Soc., 1995, 117, 9923
89. (b) R. Breslow, R. Conners and Z. N. Zhu, Pure Appl. Chem., 1996, 68, 1527
90. (c) R. Breslow, K. Groves and M. U. Mayer, Pure Appl. Chem., 1998, 70, 1933.
91. (a) R. Breslow and R. Conners, J. Am. Chem. Soc., 1996, 118, 6323
92. (b) R. Breslow K. Groves and M. U. Mayer, Org. Lett., 1999, 1, 117
93. (c) R. Breslow, K. Groves and M. U. Mayer, J. Am. Chem. Soc., 2002, 124, 3622.
94. T. Asano and W. J. LeNoble, Chem. Rev., 1978, 78, 407.
95. (a) R. Breslow, U. Maitra and D. Rideout, Tetrahedron Lett., 1983, 24, 1901
96. (b) R. Breslow and U. Maitra, Tetrahedron Lett., 1984, 25, 1239.
97. P. S. Pandey and I. K. Pandey, Tetrahedron Lett., 1997, 38, 7237.
98. (a) S. Otto, G. Boccaletti and J. B. F. N. Engberts, J. Am. Chem. Soc., 1998, 120, 4238
99. (b) S. Otto and J. B. F. N. Engberts, J. Am. Chem. Soc., 1999, 121, 6798.
100. A frequently encountered argument in the literature states that reactions with a negative volume of activation featuring nonpolar reactants will be accelerated through HI. However, it is not so much the reduction in volume as the reduction in surface area that is in contact with water that matters, although in practice area and volume terms will usually be correlated.
101. R. N. Butler, A. G. Coyne, W. J. Cunningham and L. A. Burke J. Chem. Soc., Perkin Trans. 2, 2002, 1807.