Monte Carlo simulations of the counter ion effect on the conformational equilibrium of the N, N′-diphenyl-guanidinium ion in aqueous solution

Journal of Chemical Physics

Volumn 104, Issue 4, 1996, Pages 1452-1463

  Nagy, Peter I ^a   Durant, Graham J ^b  

^a MEDICAL COLLEGE OF OHIO   (United States)

^b CeNeS Pharmaceuticals plc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011147451     PISSN: 00219606     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.470910     Document Type: Article

References (73)

1. S. Miertus, E. Scrocco, and J. Tomasi, Chem. Phys. 117,55 (1981);
2. (b) M. W. Wong, M. Frisch, and K. B. Wiberg, J. Am. Chem. Soc. 113, 4776 (1991);
3. B. Wang and G. P. Ford, J. Chem. Phys. 97, 4162 (1992).
4. For a detailed, recent review on the continuum methods, see J. Tomasi and M. Persico, Chem. Rev. 94, 2027 (1994).
5. (a) M. M. Karelson, T. Tamm, A. R. Katritzky, S. J. Cato, and M. C. Zemer, Tetrahedron Comp. Method 2, 295 (1989);
6. (b) J. Gao and J. J. Pavelites, J. Am. Chem. Soc. 114,1912 (1992);
7. (c) C. J. Cramer and D. G. Truhlar, J. Comput. Chem. 13, 1089 (1992);
8. (d) C. J. Cramer and D. G. Truhlar, J. Am. Chem. Soc. 115, 2226 (1993).
9. (a) D. L. Beveridge and F. M. DiCapua, Rev. Biophys. Biophys. Chem. 8, 431 (1989);
10. (b) Computer Simulations of Biomolecular Systems, edited by W. F. Van Gunsteren and P. K. Weiner (Escom, Leiden, The Netherlands, 1989);
11. (c) M. P. Allen and D. J. Tildesley, Computer Simulations of Liquids (OUP, New York, 1991).
12. G. E. Marlow, J. S. Perkyns, and B. M. Pettitt, Chem. Rev. 93, 2503 (1993).
13. 5(a) B. Jayaram and D. L. Beveridge, J. Phys. Chem. 94, 4666 (1990);
14. (b) B. Jayaram, F. M. DiCapua, and D. L. Beveridge, J. Am. Chem. Soc. 113, 5211 (1991).
15. 6(a) P. E. Smith and B. M. Pettitt, J. Am. Chem. Soc. 113, 6029 (1991);
16. (b) P. E. Smith, G. E. Marlow, and B. M. Pettitt, J. Am. Chem. Soc. ibid. 115, 7493 (1993).
17. V. Mohan, P. E. Smith, and B. M. Pettitt, J. Phys. Chem. 97, 12984 (1993).
18. W. S. Ross and C. C. Hardin, J. Am. Chem. Soc. 116, 6071 (1994).
19. See, e.g., (a) A. A. Rashin, J. R. Rabinowitz, and J. R. Banfelder, J. Am. Chem. Soc. 112, 4133 (1990);
20. (b) J. J. Urban, C. J. Cramer, and G. R. Famini, J. Am. Chem. Soc. ibid. 114, 8226 (1992);
21. (c) G. A. Worth and W. G. Richards, J. Am. Chem. Soc. ibid. 116, 239 (1994);
22. (d) P. I. Nagy, G. J. Durant, W. P. Hoss, and D. A. Smith, J. Am. Chem. Soc. ibid. 116, 4898 (1994).
23. (a) G. Alagona, C. Ghio, P. I. Nagy, and G. J. Durant, J. Phys. Chem. 98, 5422 (1994);
24. (b) G. Alagona and C. Ghio (personal communication).
25. 11(a) W. J. Hehre, L. Radom, P. v. R. Schleyer, and J. A. Pople, Ab Initio Molecular Orbital Theory (Wiley, New York, 1986);
26. (b) C. Moller and M. S. Plesset, Phys. Rev. 46,618 (1934);
27. (c) J. A. Pople, J. S. Binkley, and R. Seeger, Int. J. Quantum Chem. 10s, 1 (1976).
28. GAUSSIAN 92, Revision A, M. J. Frisch, G. W. Trucks, M. Head-Gordon, P. M. W. Gill, M. W. Wong, J. B. Foresman, B. G. Johnson, H. B. Schlegel, M. A. Robb, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, K.; J. S. Binkley, C. Gonzalez, R. L. Martin, D. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart, and J. A. Pople, Gaussian, Inc., Pittsburgh, Pennsylvania, 1992.
29. R. W. Zwanzig, J. Chem. Phys. 22, 1420 (1954).
30. (a) W. L. Jorgensen and C. Ravimohan, J. Chem. Phys. 83, 3050 (1985);
31. (b) W. L. Jorgensen, J. K. Buckner, S. Boudon, and J. Tirado-Rives, J. Chem. Phys. ibid. 89, 3742 (1988).
32. W. L. Jorgensen, BOSS, Version 3.4. Biochemical and Organic Simulation System User's Manual, 1993.
33. (a) W. L. Jorgensen and J. D. Madura, J. Am. Chem. Soc. 105, 1407 (1983);
34. (b) W. L. Jorgensen and C. Swenson, J. Am. Chem. Soc. ibid. 107, 1489 (1985);
35. (c) W. L. Jorgensen and J. Gao, J. Phys. Chem. 90, 2174 (1986).
36. 17(a) W. L. Jorgensen, J. Chandrasekhar, J. D. Madura, R. W. Impey, and M. L. Klein, J. Chem. Phys. 79, 926 (1983);
37. (b) W. L. Jorgensen and J. D. Madura, Mol. Phys. 56, 1381 (1985).
38. 18(a) J. C. Owicki and H. A. Scheraga, Chem. Phys. Lett. 47,600 (1977);
39. (b) W. L. Jorgensen, J. Phys. Chem. 87, 5304 (1983).
40. W. L. Jorgensen and J. Tirado-Rives, J. Am. Chem. Soc. 110,1657 (1988).
41. S. Boudon, G. Wipff, and B. Maigret, J. Phys. Chem. 94, 6056 (1990).
42. (a) U. C. Singh and P. A. Kollman, J. Comput. Chem. 5,129 (1984);
43. (b) B. H. Besler, K. M. Merz, and P. A. Kollman, J. Comput. Chem. ibid. 11,431 (1990);
44. (c) C. M. Brenaman and K. Wiberg, J. Comput. Chem. ibid. 11, 361 (1990).
45. F. M. Floris, J. Tomasi, and J. L. Pascual Ahuir, J. Comput. Chem. 12,784 (1991).
46. P. I. Nagy, W. J. Dunn III, G. Alagona, and C. Ghio, J. Am. Chem. Soc. 113, 6719 (1991);
47. P. I. Nagy, W. J. Dunn III, G. Alagona, and C. Ghio, J. Am. Chem. Soc. 114, 4752 (1992).
48. P. I. Nagy, W. J. Dunn III, G. Alagona, and C. Ghio, J. Phys. Chem. 97, 4628 (1993).
49. MacroModel V3.5a: F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, C. Caufield, G. Chang, T. Hendrickson, and W. C. Still, W. J. Comput. Chem. 11, 440 (1990).
50. P. I. Nagy, J. E. Bitar, and D. A. Smith, J. Comput. Chem. 15, 1228 (1994).
51. J. Gao, J. Phys. Chem. 96, 537 (1992).
52. M. Orozco, W. L. Jorgensen, and F. J. Luque, J. Comput. Chem. 14, 1498 (1993).
53. H. A. Carlson, T. B. Nguyen, M. Orozco, and W. L. Jorgensen, J. Comput. Chem. 14, 1240 (1993).
54. See, e.g. (a) W. L. Jorgensen, J. K. Buckner, S. E. Huston, and P. J. Rossky, J. Am. Chem. Soc. 109, 1891 (1987);
55. (b) J. K. Buckner and W. L. Jorgensen, J. Am. Chem. Soc. ibid. 111, 2507 (1989);
56. (c) J. Gao, J. Phys. Chem. 98, 6049 (1994);
57. (d) D. E. Smith and L. X. Dang, J. Chem. Phys. 100, 3757 (1994);
58. (e) S. W. Chen and P. J. Rossky, J. Phys. Chem. 97, 6078 (1993);
59. (f) J. Perkyns and B. M. Pettitt, J. Phys. Chem. ibid. 98, 5147 (1994).
60. (a) F. Hirata, B. M. Pettitt, and P. J. Rossky, J. Chem. Phys. 77, 509 (1982);
61. (b) F. Hirata, P. J. Rossky, and B. M. Pettitt, J. Chem. Phys. ibid. 78,4133 (1983).
62. (a) J. S. Perkyns and B. M. Pettitt, J. Chem. Phys. 97, 7656 (1992);
63. (b) Chem. Phys. Lett. 190, 626 (1992).
64. W. L. Jorgensen, J. K. Buckner, and J. Gao, in Chemical Reactivity in Liquids, edited by M. Moreau and P. Turq (Plenum, New York, 1988), p. 253.
65. M. Born, Z. Phys. 1, 45 (1920).
66. S. M. Cybulski and S. Scheiner, J. Phys. Chem. 93, 6565 (1989).
67. P. I. Nagy, D. A. Smith, G. Alagona, and C. Ghio, J. Phys. Chem. 98, 486 (1994).
68. (a) P. I. Nagy, G. J. Durant, and D. A. Smith, J. Am. Chem. Soc. 115, 2912 (1993);
69. (b) P. Nagy, Acta Chim. Hung. 129, 429 (1992).
70. F. C. Bernstein, T. F. Koetzle, G. J. B. Williams, E. F. Mayer, M. D. Brice, J. R. Rogers, O. Kennard, T. Shimanouchi, and T. Tasumi, J. Mol. Biol. 122, 535 (1977).
71. 39(a) P. Nagy, J. Comput. Aided Molec. Design 2, 65 (1988);
72. (b) G. Naray-Szabo and P. Nagy, Int. J. Quantum Chem. 35, 215 (1989).
73. M. Aida, J. Mol. Struct. (Theochem) 311, 45 (1994).