Quantum mechanical/effective fragment potential (QM/EFP) study of phosphate monoester aminolysis in aqueous solution

Journal of Physical Chemistry B

Volumn 113, Issue 44, 2009, Pages 14831-14836

  Ferreira, Dalva E C ^a   Florentino, Bruno P D ^a   Rocha, Willian R ^a   Nome, Faruk ^b  

^a Belo Horizonte   (Brazil)

^b FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE DISTRIBUTION; CHARGE TRANSFER; CHARGED PARTICLES; COMPUTER SIMULATION; DISTRIBUTION FUNCTIONS; FLUORINE CONTAINING POLYMERS; ION EXCHANGE; MONTE CARLO METHODS; NUCLEOPHILES; PHOSPHORUS;

ACTIVATION FREE ENERGY; AMINOLYSIS; AQUEOUS SOLUTIONS; BOND DISSOCIATION; CONCERTED MECHANISM; ENERGETIC PROPERTIES; EXPERIMENTAL VALUES; FRAGMENT POTENTIAL; LEAVING GROUPS; MONOESTERS; MONTE CARLO SIMULATION; NEW STRATEGY; NITROGEN ATOM; P-NITROPHENYL PHOSPHATE; P-O BONDS; RADIAL PAIR DISTRIBUTION FUNCTION; REACTION COORDINATES; REACTION MECHANISM; TRANSITION STATE;

ACTIVATION ENERGY;

EID: 72449162608     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp907014r     Document Type: Article

References (58)

1. Westheimer, F. H. Science 1987, 235, 1173.
2. Yang, Y. C.; Baker, J. A.; Ward, J. R. Chem. Rev. 1992, 92, 1729.
3. Domingos, J. B.; Longhinotti, E.; Machado, V. G.; F; Nome, F. Quim. NoVa 2003, 26, 745.
4. Kamerlin, S. C. L.; Wilkie, J. Org. Biomol. Chem. 2007, 5, 2098.
5. Kirby, A. J.; Younas, M. J. Chem. Soc. B 1970, 6, 510.
6. Mitic, N.; Smith, S. J.; Neves, A.; Guddat, L. W.; Gahan, L. R.; Schenk, G. Chem. Rev. 2006, 106, 3338.
7. Ferreira, D. E. C.; De Almeida, W. B.; Neves, A.; Rocha, W. R. Phys. Chem. Chem. Phys. 2008, 46, 7039.
8. Wilcox, D. E. Chem. Rev. 1996, 96, 2435.
9. Florián, J.; Warshel, A. J. Phys. Chem. B 1998, 102, 719.
10. Iché-Tarrat, N.; Barthelat, J. C.; Rinaldi, D.; Vigroux, A. J. Phys. Chem. B 2005, 109, 22570.
11. Kamerlin, S. C. L.; Wilkie, J. Org. Biomol. Chem. 2007, 5, 2098.
12. Longhinotti, E.; Domingos, J. B.; Da Silva, P. L. F.; Szpoganicz, B.; Nome, F. J. Phys. Org. Chem. 2005, 18, 167.
13. Dejaegere, A.; Liang, X.; Karplus, M. J. Chem. Soc., Faraday Trans. 1994, 90, 1763.
14. Chen, X.; Zhan, C. G. J. Phys. Chem. A 2004, 108, 3789.
15. Chen, X.; Zhan, C. G. J. Phys. Chem. A 2004, 108, 6407.
16. Kirby, A. J.; Jencks, W. P. J. Am. Chem. Soc. 1965, 87, 3217.
17. Kirby, A. J.; Jencks, W. P. J. Am. Chem. Soc. 1965, 87, 3209.
18. Hengge, A. C.; Edens, W. A.; Elsing, H. J. Am. Chem. Soc. 1994, 116, 5045.
19. Zhang, L.; Xie, D.; Xu, D.; Guo, H. Chem. Commun. 2007, 1638.
20. Kamerlin, S. C.; Williams, N. H.; Warshel, A. J. Org. Chem. 2008, 73, 6960.
21. Parks, J. M.; Hu, H.; Rudolph, J.; Yang, W. T. J. Phys. Chem. B 2009, 113, 5217.
22. Loacute;pez-Canut, V.; Martí, S.; Bertrán, J.; Moliner, V.; Tuñoacute;n, I. J. Phys. Chem. B 2009, 113, 7816.
23. Jardin, C.; Horn, A. H. C.; Schorer, G.; Sticht, H. J. Phys. Chem. B 2008, 112, 13391.
24. De Vivo, M.; Ensing, B.; Klein, M. L. J. Am. Chem. Soc. 2005, 127, 11226.
25. De Vivo, M.; Dal Peraro, M.; Klein, M. L. J. Am. Chem. Soc. 2008, 130, 10955.
26. Grigorenko, B. L.; Rogov, A. V.; Nemukhin, A. V. J. Phys. Chem. B 2006, 110, 4407.
27. Adamovic, I.; Freitag, M. A.; Gordon, M. S. J. Chem. Phys. 2003, 118, 6725.
28. Gordon, M. S.; Freitag, M. A.; Bandyopadhyay, P.; Jensen, J. H.; Kairys, V.; Stevens, W. J. J. Phys Chem A 2001, 105, 293.
29. Day, P. N.; Jensen, J. H.; Gordon, M. S.; Webb, S. P.; Stevens, W. J.; Krauss, M.; Garmer, D.; Basch, H.; Cohen, D. J. Chem. Phys. 1996, 105, 1968.
30. Chen, W.; Gordon, M. S. J. Chem. Phys. 1996, 105, 11081.
31. Day, P. N.; Pachter, R.; Gordon, M. S.; Merrill, G. N. J. Chem. Phys. 2000, 112, 2063.
32. Adamovic, I.; Gordon, M. S. J. Phys. Chem. A 2005, 109, 1629.
33. Slipchenko, L. V.; Gordon, M. S. J. Phys. Chem. A 2009, 113, 2092.
34. Yoo, S.; Zahariev, F.; Sok, S.; Gordon, M. S. J. Chem. Phys. 2008, 129, 144112.
35. Aguilar, C. M.; De Almeida, W. B.; Rocha, W. R. Chem. Phys. Lett. 2007, 449, 144.
36. Aguilar, C. M.; De Almeida, W. B.; Rocha, W. R. Chem. Phys. 2008, 353, 66.
37. Allen, M. P.; Tildesley, D. J. Computer Simulation of Liquids; Oxford University Press, Clarendon: New York, 1987.
38. Metropolis, N.; Rosenbluth, A. W.; Rosenbluth, M. N.; Teller, A. H.; Teller, E. J. Chem. Phys. 1953, 21, 1087.
39. Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecule; Oxford University Press: Oxford, 1989.
40. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
41. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
42. Breneman, C. M.; Wiberg, K. B. J. Comput. Chem. 1990, 11, 361.
43. Jorgensen, W. L.; Madura, J. D.; Swenson, C. J. J. Am. Chem. Soc. 1984, 106, 6638.
44. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J. D.; Impey, R. W.; Klein, M. J. Chem. Phys. 1983, 79, 926.
45. Kirkpatrick, S.; Gelatt, C. D.; Vecci, M. P. Science 1983, 220, 671.
46. Fukui, K. Acc. Chem. Res. 1981, 14, 363.
47. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154.
48. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523.
49. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
50. See for example Szabo, A.; Ostlund, N. S. Modern Quantum Chemistry, Introduction to Advanced Electronic Structure Theory; Dover Publication, Inc.: New York, 1996.
51. Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1993, 98, 1358.
52. Kendall, R. A.; Dunning, T. H., Jr. J. Chem. Phys. 1992, 96, 6796.
53. Coutinho; K.; Canuto, S. DICE: A Monte Carlo Program for Liquid Simulation; University of São Paulo, 1997.
54. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347.
55. Ma, B.; Xie, Y.; Shen, M.; Schaefer, H. F. J. Am. Chem. Soc. 1993, 115, 1943.
56. Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027.
57. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999.
58. Pascual-Ahuir, J. L.; Silla, E.; Tomasi, J.; Bonaccorsi, R. J. Comput. Chem. 1987, 8, 778.