Quantifying intermolecular interactions: Guidelines for the molecular recognition toolbox

Angewandte Chemie - International Edition

Volumn 43, Issue 40, 2004, Pages 5310-5324

  Hunter, Christopher A ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

Formation enthalpy; Hydrogen bonds; Molecular recognition; Solvent effects; Statistical thermodynamics

Indexed keywords

HYDROGEN BONDS; HYDROPHOBICITY; POSITIVE IONS; THERMODYNAMICS;

INTERMOLECULAR INTERACTIONS; MOLECULAR RECOGNITION;

MOLECULAR DYNAMICS;

SOLVENT;

AQUEOUS SOLUTION; CHEMICAL STRUCTURE; ELECTRICITY; ENTHALPY; HYDROGEN BOND; HYDROPHOBICITY; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; PHASE TRANSITION; PHENOMENOLOGY; QUANTITATIVE ANALYSIS; REVIEW; ROOM TEMPERATURE; SOLID STATE; SOLUBILITY; SOLVATION; THEORETICAL MODEL; THERMODYNAMICS; X RAY DIFFRACTION;

EID: 7244258931     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200301739     Document Type: Review

References (77)

1. a) A. R. Fersht in Enzyme Structure and Mechanism, Freeman, New York, 1985;
2. b) W. P. Jencks in Catalysis in Chemistry and Enzymology, Dover, New York, 1987;
3. c) J. Rebek, Acc. Chem. Res. 1990, 23, 399-404;
4. d) H. J. Schneider, Angew. Chem., 1991, 103, 1419-1439; Angew. Chem. Int. Ed. Engl. 1991, 30, 1417-1436;
5. d) H. J. Schneider, Angew. Chem., 1991, 103, 1419-1439; Angew. Chem. Int. Ed. Engl. 1991, 30, 1417-1436;
6. e) F. Vogtle in Supramolecular Chemistry, Wiley, New York, 1991;
7. f) J. M. Lehn in Supramolecular Chemistry, VCH, Weinheim, 1995;
8. g) J. C. Ma, D. A. Dougherty, Chem. Rev. 1997, 97, 1303-1324;
9. h) C. G. Claessens, J. F. Stoddart, J. Phys. Org. Chem. 1997, 10, 254-272;
10. i) W. W. Cleland, P. A. Frey, J. A. Gerlt, J. Biol. Chem. 1998, 273, 25529-25532;
11. j) W. W. du Mont, F. Ruthe, Coord. Chem. Rev. 1999, 189, 101-133;
12. k) A. M. Davis, S. J. Teague, Angew. Chem. 1999, 111, 778-792; Angew. Chem. Int. Ed. 1999, 38, 736-749;
13. k) A. M. Davis, S. J. Teague, Angew. Chem. 1999, 111, 778-792; Angew. Chem. Int. Ed. 1999, 38, 736-749;
14. l) J. W. Steed, J. L. Atwood in Supramolecular Chemistry, Wiley, Chichester, 2000;
15. m) H. J. Schneider, A. Yatsimirsky in Principles and Methods in Supramolecular Chemistry, Wiley, Chichester, 2000;
16. n) C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc. Perkin Trans. 2 2001, 651-669;
17. o) T. Lazaridis, Acc. Chem. Res. 2001, 34, 931-937;
18. p) T. Steiner, Angew. Chem. 2002, 114, 50-80; Angew. Chem. Int. Ed. 2002, 41, 48-76;
19. p) T. Steiner, Angew. Chem. 2002, 114, 50-80; Angew. Chem. Int. Ed. 2002, 41, 48-76;
20. q) E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. 2003, 115, 1244-1287; Angew. Chem. Int. Ed. 2003, 42, 1210-1250.
21. q) E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. 2003, 115, 1244-1287; Angew. Chem. Int. Ed. 2003, 42, 1210-1250.
22. a) M. J. Stone, Acc. Chem. Res. 2001, 34, 379-388;
23. b) D. H. Williams, D. P. O'Brien, B. Bardsley, J. Am. Chem. Soc. 2001, 123, 737-738;
24. c) C. T. Calderone, D. H. Williams, J. Am. Chem. Soc. 2001, 123, 6262-6267;
25. d) F. P. Schmidtchen, Chem. Eur. J. 2002, 8, 3522-3529;
26. e) K. N. Houk, A. G. Leach, S. P. Kim, X. Zhang, Angew. Chem. 2003, 115, 5020-5046; Angew. Chem. Int. Ed. 2003, 42, 4872-4897.
27. e) K. N. Houk, A. G. Leach, S. P. Kim, X. Zhang, Angew. Chem. 2003, 115, 5020-5046; Angew. Chem. Int. Ed. 2003, 42, 4872-4897.
28. a) C. Tanford in The Hydrophobic Effect: Formation of Micelles and Biological Membranes, Wiley, New York, 1973;
29. b) B. Lee, Proc. Natl. Acad. Sci. USA 1991, 88, 5154-5158;
30. c) N. T. Southhall, K. A. Dill, A. D. J. Haymet, J. Phys. Chem. B 2002, 106, 521-533.
31. M. S. Searle, D. H. Williams, J. Am. Chem. Soc. 1992, 114, 10690-10697.
32. a) W. P. Jencks, Proc. Natl. Acad. Sci. USA 1981, 78, 4046-4050;
33. b) P. R. Andrews, D. J. Craik, J. L. Martin, J. Med. Chem. 1984, 27, 1648-1657;
34. c) A. Matouschek, A. R. Fersht, Methods Enzymol 1991, 202, 82-112;
35. d) H. J. Schneider, Chem. Soc. Rev. 1994, 23, 227-234;
36. e) D. H. Williams, M.S. Westwell, Chem. Soc. Rev. 1998, 27, 57-63;
37. f) C. A. Hunter, P. S. Jones, P. Tiger, S. Tomas, Chem. Eur. J. 2002, 8, 5435-5446.
38. M. Rigby, E. B. Smith, W. A. Wakeham, G. C. Maitland in The Forces Between Molecules, Clarendon, Oxford, 1986.
39. Sometimes a fifth component, the charge transfer interaction, is considered, but for most organic molecules, the magnitudes of such effects are negligible in the ground state of a complex.
40. A. P. Bisson, C. A. Hunter, J. C. Morales, K. Young, Chem. Eur. J. 1998, 4, 845-851.
41. J. Jadzyn, M. Stockhausen, B. Zywucki, J. Phys. Chem. 1987, 91, 754-757.
42. a) J. C. Slater, J. G. Kirkwood, Phys. Rev. 1931, 37, 682-697;
43. b) CRC handbook of Chemistry and Physics, 72nd ed. (Ed.: D. R. Lide), CRC, Boca Raton, FL, 1991.
44. The values for hydrogen are not included in Table 2, due to uncertainties in defining the relevant surface area.
45. There are some special cases where the geometry of a binding pocket prevents solvation, and here, dramatic enhancements in the association constant are observed, because the solvent is unable to compensate for the gain in solute-solute dispersion interactions. K. T. Chapman, W. C. Still, J. Am. Chem. Soc. 1989, 111, 3075-3077.
46. S. Tsuzuki, K. Tanabe, J. Phys. Chem. 1991, 95, 2272-2278.
47. M. H. Abraham, J. A. Platts, J. Org. Chem. 2001, 66, 3484-3491.
48. L. Pauling, Proc. Natl. Acad. Sci. USA 1928, 14, 359.
49. a) H. Hagelin, J. S. Murray, T. Brinck, M. Berthelot, P. Politzer, Can. J. Chem. 1995, 73, 483-488;
50. b) J. C. Dearden, T. Ghafourian, J. Chem. Inf. Comput. Sci. 1999, 39, 231-235;
51. c) J. A. Platts, Phys. Chem. Chem. Phys. 2000, 2, 973-980;
52. d) J. A. Platts, Phys. Chem. Chem. Phys. 2000, 2, 3115-3120;
53. e) A. M. Zissimos, M. H. Abraham, A. Klamt, F. Eckert, J. Wood, J. Chem. Inf. Comput. Sci. 2002, 42, 1320-1331.
54. M. I. Page, W. P. Jencks, Proc. Natl. Acad. Sci. USA 1971, 68, 1678-1683.
55. H.-J. Bohm, J. Comput.-Aided Mol. Des. 1994, 8, 243-256.
56. a) F. H. Westheimer, L. L. Ingraham, J. Phys. Chem. 1956, 60, 1668;
57. b) H.L. Anderson, Inorg. Chem. 1994, 33, 972-981;
58. c) H. L. Anderson, S. Anderson, J. K. M. Sanders, J. Chem. Soc. Perkin Trans. 1 1995, 2231-2245;
59. d) X. Chi, A. J. Guerin, R. A. Haycock, C. A. Hunter, L. D. Sarson, J. Chem. Soc. Chem. Commun. 1995, 2563-2565.
60. For the functional groups described in reference [14] the simplest molecule containing the relevant functional group was constructed by using Spartan'02 (Wavefuntion, Inc., Irvine CA), for example, methyl acetate was used to calculate the properties of the ester. The molecules were optimized by using AM1, and the maxima and minima in the molecular electrostatic potential surface were determined.
61. Dimethyl ether was used to calculate the interaction profile, because it contains only one type of hydrogen-bond donor and one type of hydrogen-bond acceptor. However, the assumption is that the diethyl ether profile, which is more relevant to experiments at room temperature, is very similar.
62. a) M. H. Abraham, P. L. Grellier, D. V. Prior, R. W. Taft, J. L. Morris, P. J. Taylor, C. Laurence, M. Berthelot, R. M. Doherty, M. J. Kamlet, J.-L. Abboud, K. Sraidi, G. Guiheneuf, J. Am. Chem. Soc. 1988, 110, 8534;
63. b) J. Marco, J. M. Orza, R. Notario, J.-L. M. Abboud, J. Am. Chem. Soc. 1994, 116, 8841-8842;
64. c) M. H. Abraham, M. Berthelot, C. Laurence, P. J. Taylor, J. Chem. Soc. Perkin Trans. 2 1998, 187-191.
65. a) J. Rubin, B. Z. Senkowski, G. S. Panson, J. Phys. Chem. 1964, 68, 1601-1602;
66. b) J. Rubin, G. S. Panson, J. Phys. Chem. 1965, 69, 3089-3091;
67. c) R. W. Taft, D. Gurka, L. Joris, P. von R. Schleyer, J. W. Rakshys, J. Am. Chem. Soc. 1969, 91, 4801-4808;
68. d) M. J. Kamlet, J. F. Gal, P. C. Maria, R. W. Taft, J. Chem. Soc. Perkin Trans. 2 1985, 1583-1589.
69. F. Besseau, M. Lucon, C. Laurence, M. Berthelot, J. Chem. Soc. Perkin Trans. 2 1998, 101-107.
70. a) W. L. Jorgensen, J. Pranata, J. Am. Chem. Soc. 1990, 112, 2008-2010;
71. b) T. J. Murray, S. C. Zimmerman, J. Am. Chem. Soc. 1992, 114, 4010-4011;
72. c) J. Sartorius, H. J. Schneider, Chem. Eur. J. 1996, 2, 1446-1452.
73. C. A. Hunter, C. M. R. Low, C. Rotger, J. G. Vinter, C. Zonta, Chem. Commun. 2003, 834-835.
74. M. W. Hosseini, Coord. Chem. Rev. 2003, 240, 157-166.
75. a) H. J. Schneider, V. Rudiger, O. A. Raevsky, J. Org. Chem. 1993, 58, 3648-3653;
76. b) H. Gohlke, G. Klebe, Angew. Chem. 2002, 114, 2764-2798; Angew. Chem. Int. Ed. 2002, 41, 2645-2676.
77. b) H. Gohlke, G. Klebe, Angew. Chem. 2002, 114, 2764-2798; Angew. Chem. Int. Ed. 2002, 41, 2645-2676.