Monte Carlo investigations of solvent effects on the decarboxylation reaction of neutral N-carboxy-2-imidazolidinone in aqueous solution

Journal of Organic Chemistry

Volumn 64, Issue 12, 1999, Pages 4492-4501

  Gao, Daqing ^a   Pan, Yuh Kang ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYL GROUP; HYDANTOIN DERIVATIVE; SOLVENT;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; DECARBOXYLATION; PROTON TRANSPORT; REACTION ANALYSIS; SIMULATION; SOLVATION; STRUCTURE ANALYSIS; SYSTEM ANALYSIS;

EID: 0033546387     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9904563     Document Type: Article

References (112)

1. For a thorough review, see: (a) Knowles, J. R. Annu. Rev. Biochem. 1989, 58, 195. (b) Annals of the New York Academy of Sciences; Dakshinamurti, K., Bhagavan, H. N., Eds.; New York Academy of Sciences: New York, 1985; Vol. 447.
2. For a thorough review, see: (a) Knowles, J. R. Annu. Rev. Biochem. 1989, 58, 195. (b) Annals of the New York Academy of Sciences; Dakshinamurti, K., Bhagavan, H. N., Eds.; New York Academy of Sciences: New York, 1985; Vol. 447.
3. (a) Lynen, F.; Knappe, J.; Lorch, E.; Jutting, G.; Ringelmann, E. Angew. Chem. 1959, 71, 481.
4. (b) Kaziro, Y.; Hase, L. F.; Boyer, P. D.; Ochoa, S. J. Biol. Chem. 1962, 237, 1460.
5. (c) Hegarty, A. F.; Pratt, R. F.; Guidici, T.; Bruice, T. C. J. Am. Chem. Soc. 1971, 93, 1428.
6. (d) DeTitta, G. T.; Edmonds, J. W.; Stallings, W.; Donohue, J. J. Am. Chem. Soc. 1976, 98, 1920.
7. (e) Stubbe, J.; Fish, S.; Abeles, R. H. J. Biol. Chem. 1980, 255, 236.
8. (f) Fry, D. C.; Fox, T. L.; Lane, M. D.; Mildvan, A. S. J. Am. Chem. Soc. 1985, 107, 7659.
9. (g) Berkessel, A.; Breslow, R. Bioorg. Chem. 1986, 14, 249.
10. (h) Perrin, C. L.; Tammy, J. D. J. Am. Chem. Soc. 1987, 109, 5163.
11. (i) Waldrop, G. L.; Rayment, I.; Holden, H. M. Biochemistry 1994, 33, 10249.
12. (a) Thatcher, G. R. J.; Poirier, R.; Kluger, R. J. Am. Chem. Soc. 1986, 108, 2699.
13. (b) DeTitta, G. T.; Blessing, R. H.; Moss, G. R.; King, H. F.; Sukumaran, D. K.; Roskwitalski, R. L. J. Am. Chem. Soc. 1994, 116, 6485.
14. (c) Li, N.; Maluendes, S.; Blessing, R. H.; Dupuis, M.; Moss, G. R.; DeTitta, G. T. J. Am. Chem. Soc. 1994, 116, 6494.
15. (d) Grant, A. S. J. Mol. Struct. (THEOCHEM) 1998, 422, 79.
16. (e) Miyamoto, S.; Kollman, P. A. Proteins 1993, 16, 226.
17. Gao, D.; Pan, Y.-K. J. Org. Chem. 1999, 64, 1159.
18. Rahil, J.; You, S.; Kluger, R. J. Am. Chem. Soc. 1996, 118, 12495.
19. Tipton, P. A.; Cleland, W. W. J. Am. Chem. Soc. 1988, 110, 5866.
20. Attwood, P. V.; Tipton, P. A.; Cleland, W. W. Biochemistry 1986, 25, 8197.
21. (a) Caplow, M. J. Am. Chem. Soc. 1965, 87, 5774.
22. (b) Caplow, M.; Yager, M. J. Am. Chem. Soc. 1967, 89, 4513.
23. (a) Kemp, D. S.; Cox, D. D.; Paul, K. G. J. Am. Chem. Soc. 1975, 97, 7312.
24. (b) Tarasow, T. M.; Lewis, C.; Hilvert, D. J. Am. Chem. Soc. 1994, 116, 7959.
25. (c) Smiley, J. A.; Benkovic, S. J. J. Am. Chem. Soc. 1995, 117, 3877.
26. (d) Sun, S.; Smith, G. S.; O'Leary, M. H.; Schowen, R. L. J. Am. Chem. Soc. 1997, 119, 1507.
27. (e) Miller, B. G.; Traut, T. W.; Wolfenden, R. J. Am. Chem. Soc. 1998, 120, 2666.
28. (a) Zipse, H.; Apaydin, G.; Houk, K. N. J. Am. Chem. Soc. 1995, 117, 8608.
29. (b) Gao, J. J. Am. Chem. Soc. 1995, 117, 8600.
30. (c) Huang, C.-L.; Wu, C.-C.; Lien, M.-H. J. Phys. Chem. A 1997, 101, 7867.
31. (d) Bach, R. D.; Canepa, C. J. Org. Chem. 1996, 61, 6346.
32. (e) Bach, R. D.; Canepa, C. J. Am. Chem. Soc. 1997, 119, 11725.
33. (f) Lee, J. K.; Houk, K. Science 1997, 276, 942.
34. (a) Westheimer, F. H. Tetrahedron 1995, 51, 3.
35. (b) Logue, M. W.; Pollack, R. M.; Vitullo, V. P. J. Am. Chem. Soc. 1975, 97, 6868.
36. (c) Straub, T. S.; Bender, M. L. J. Am. Chem. Soc. 1972, 94, 8881.
37. (d) Brower, K. R.; Gay, B.; Konkol, T. L. J. Am. Chem. Soc. 1966, 88, 1681.
38. (e) Bigley, D. B.; Thurman, J. C. J. Chem. Soc. B 1968, 436.
39. (f) Swain, C. G.; Bader, R. F. W.; Esteve, R. M., Jr.; Griffin, R. N. J. Am. Chem. Soc. 1961, 83, 1951.
40. (g) Steinberger, R.; Westheimer, F. H. J. Am. Chem. Soc. 1951, 73, 429.
41. (h) Westheimer, F. H.; Jones, W. A. J. Am. Chem. Soc. 1941, 63, 3283.
42. (i) Pedersen, K. J. J. Am. Chem. Soc. 1938, 60, 595.
43. (j) Pedersen. K. J. J. Phys. Chem. 1934, 38, 559.
44. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523.
45. (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Wong, M. W.; Foresman, J. B.; Robb, M. A.; Head-Gordon, M.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. L.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92/DFT, Revision G3; Gaussian, Inc.: Pittsburgh, PA, 1993.
46. (b) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. L.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision E.2; Gaussian, Inc.: Pittsburgh, PA, 1995.
47. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294.
48. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; John Wiley and Sons: New York, 1986.
49. Grev, R. S.; Janssen, C. L.; Schaefer, H. F.; III. J. Chem. Phys. 1991, 95, 5128.
50. (a) Warshel, A.; Levitt, M. J. Mol. Biol. 1976, 103, 227.
51. (b) Warshel, A.; Lappicirella, A. J. Am. Chem. Soc. 1981, 103, 4664.
52. (c) Luzhkov, V.; Warshel, A. J Comput. Chem. 1992, 13, 199.
53. (d) Åqvist, J.; Warshel, A. Chem. Rev. 1993, 93, 2523.
54. (a) Singh, U. C.; Kollman, P. A. J. Comput. Chem. 1986, 7, 718.
55. (b) Stanton, R. V.; Peräkylä, M.; Bakowies, D.; Kollman, P. A. J. Am. Chem. Soc. 1998, 120, 3448.
56. (c) Tapia, O.; Colonna, F.; Angyan, J. G. J. Chem. Phys. Phys.-Chim. Biol. 1990, 87, 875.
57. (d) Thole, B. T.; van Duijnen, P. Th. Chem. Phys. 1982, 71, 211.
58. (a) Bash, P. A.; Field, M. J.; Karplus, M. J. Am. Chem. Soc. 1987, 109, 8092.
59. (b) Field, M. J.; Bash, P. A.; Karplus, M. J. Comput. Chem. 1990, 11, 700.
60. (c) Bash, P. A.; Field, M. J.; Davenport, R. C.; Petsko, G. A.; Ringe, D.; Karplus, M. Biochemistry 1991, 30, 5826.
61. (a) Thompson, M. A.; Schenter, G. K. J. Phys. Chem. 1995, 99, 6374.
62. (b) Hartsough, D. S.; Merz, K. M., Jr. J. Phys. Chem. 1995, 99, 384.
63. (c) Liu, H.; Shi, Y. J. Comput. Chem. 1994, 15, 1331.
64. (d) Stanton, R. V.; Hartsough, D. S.; Merz, K. M., Jr. J. Phys. Chem. 1993, 97, 11868.
65. (e) Wei, D.; Salahub, D. R. Chem. Phys. Lett. 1994, 224, 291.
66. (f) Liu, H.; Muller-Plathe, F.; van Gunsteren, W. F. J. Chem. Phys. 1995, 102, 1702.
67. (g) Chatfield, D. C.; Brooks, B. R. J. Am. Chem. Soc. 1995, 117, 5561.
68. (h) Barnes, J. A.; Williams, I. H. Chem. Commun. 1996, 193.
69. (i) Bakowis, D.; Thiel, W. J. Phys. Chem. 1996, 100, 10580.
70. (j) Ho, L. L.; MacKerell, A. D., Jr.; Bash, P. A. J. Phys. Chem. 1996, 100, 4466.
71. (k) Gao, J. J. Comput. Chem. 1997, 18, 1061
72. (l) Alhambra, C.; Wu, L.; Zhang, Z.-Y.; Gao, J. J. Am. Chem. Soc. 1998, 120, 3858.
73. (m) Antonczak, S.; Monard, G.; Ruiz-López, M. F.; Rivail, J.-L. J. Am. Chem. Soc. 1998, 120, 8825.
74. (a) Gao, J.; Xia, X. Science 1992, 258, 631.
75. (b) Gao, J. In Reviews in Computational Chemistry; VCH: New York, 1995; Vol. 7.
76. (c) Gao, J. Acc. Chem. Res. 1996, 29, 298.
77. Kaminski, G. A.; Jorgensen, W. L. J. Phys. Chem. B 1998, 102, 1787.
78. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
79. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J. D.; Impey, R. W.; Klein, M. L. J. Chem. Phys. 1983, 79, 926.
80. (a) Warshel, A. Computer Modeling of Chemical Reactions in Enzymes and Solutions; John Wiley & Sons: New York, 1991.
81. (b) Allen, M. P.; Tildesley, D. J. Computer Simulations of Liquids; Clarendon Press: Oxford, 1987.
82. Zwanzig, R. W. J. Chem. Phys. 1954, 22, 1420.
83. (a) Jorgensen, W. L.; Ravimohan, C. J. Chem. Phys. 1985, 83, 3050.
84. (b) Kollman, P. A. Chem. Rev. 1993, 93, 2395.
85. Warshel, A.; Muller, R. P. J. Phys. Chem. 1995, 99, 17516.
86. Metropolis, N.; Rosenbluth, A. W.; Rosenbluth, M. N.; Teller, A. H.; Teller, E. J. Chem. Phys. 1953, 21, 1087.
87. (a) Owicki, J. C.; Scheraga, H. A. Chem. Phys. Lett. 1977, 47, 600.
88. (b) Owicki, J. C. ACS Symp. Ser. 1978, 86, 159.
89. (c) Jorgensen, W. L.; Bigot, B.; Chandrasekhar, J. J. Am. Chem. Soc. 1982, 104, 4584.
90. (a) Gao, J. MCQUB, SUNY at Buffalo, 1997.
91. (b) Stewart, J. J. P. MOPAC, Version 5. QCPE 1986, 6, 455, No. 391.
92. (c) Jorgensen, W. L. BOSS, Version 2.9; Yale University: New Haven, CT, 1990.
93. (a) Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1989, 111, 4505.
94. (b) Wang, X.; Houk, K. N. J. Am. Chem. Soc. 1988, 110, 1870.
95. (c) Wiberg, K. B.; Laidig, K. E. J. Am. Chem. Soc. 1987, 109, 5935.
96. (d) Wiberg. K. B.; Laidig, K. E. J. Am. Chem. Soc. 1988, 110, 1872.
97. (a) Gao, J.; Pavelites, J. J. J. Am. Chem. Soc. 1992, 114, 1912.
98. (b) Tadayoni, B. M.; Rebek, J. Jr. Bioog. Med. Chem. Lett. 1991, 1, 13.
99. (a) Onsager, L. J. Am. Chem. Soc. 1936, 58, 1486.
100. (b) Wong, M. W.; Frisch, M. J.; Wiberg, K. B. J. Am. Chem. Soc. 1991, 113, 4776.
101. (a) Miertus, S.; Scrocco, E.; Tomasi, J. Chem Phys. 1981, 55, 117.
102. (b) Wiberg, K. B.; Castejon, H.; Keith, T. A. J. Comput. Chem. 1996, 17, 185.
103. ≠ = 20.7 kcal/mol at pH 6.1. Corrections: Rahil, J.; You, S.; Kluger, R. J. Am. Chem. Soc. 1998, 120, 2692.
104. Olah, G. A.; White, A. M. J. Am. Chem. Soc. 1968, 90, 6087.
105. (a) Gao, J. J. Am. Chem. Soc. 1991, 113, 7796.
106. (b) Peng, Z.; Merz, K. M., Jr. J. Am. Chem. Soc. 1992, 114, 2733.
107. (c) Chang, N.-Y.; Lim, C. J. Am. Chem. Soc. 1998, 120, 2156.
108. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
109. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
110. Hwang, J. K.; Warshel, A. J. Am. Chem. Soc. 1996, 118, 11745.
111. For a review of recent theoretical work on proton-transfer reactions in solution, see: Bertran, J. Theor. Chem. Acc. 1998, 99, 143 and references therein.
112. Warshel, A.; Florian, J. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 5950.