Solvent effects on the barrier to C - N bond rotation in N,N- dimethylaminoacrylonitrile: Modeling by reaction field theory and by Monte Carlo simulations

Journal of the American Chemical Society

Volumn 121, Issue 1, 1999, Pages 227-237

  Rablen, Paul R ^a   Pearlman, Shoshannah A ^a   Miller, Deborah A ^a  

^a SWARTHMORE COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLONITRILE;

ARTICLE; CHEMICAL BINDING; CHEMICAL BOND; MATHEMATICAL MODEL; MOLECULAR INTERACTION; MOLECULAR MODEL; STRUCTURE ANALYSIS; SYSTEM ANALYSIS;

EID: 84962418529     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9823058     Document Type: Article

References (110)

1. For reviews of continuum solvation models, see: (a) Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027-2094. (b) Cramer, C. J.; Truhlar, D. G. Rev. Comput. Chem. 1990, 6, 1-72.
2. For reviews of continuum solvation models, see: (a) Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027-2094. (b) Cramer, C. J.; Truhlar, D. G. Rev. Comput. Chem. 1990, 6, 1-72.
3. (a) Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 106, 5151-5158 and references therein.
4. (b) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117-129.
5. (c) Tomasi, J.; Bonaccorsi, R.; Cammi, R.; Valle, F. O. J. J. Mol. Struct. 1991, 234, 401.
6. Foresman, J.; Keith, T. A.; Wiberg, K. B.; Snoonian, J.; Frisch, M. J. Phys. Chem. 1996, 100, 16098-16104.
7. Kollman, P. A. Chem. Rev. 1993, 93, 2395-2417.
8. (a) Jorgensen, W. L. Acc. Chem. Res. 1989, 22, 184-189.
9. (b) Jorgensen, W. L. J. Phys. Chem. 1983, 87, 5304-5314.
10. (a) Gao, J.; Freindorf, M. J. Phys. Chem. A 1997, 101, 3182-3188.
11. (b) Gao, J. L. Acc. Chem. Res. 1996, 29, 298-305.
12. (c) Gao, J.; Alhambra, C. J. Am. Chem. Soc. 1997, 119, 2962-2963.
13. Marten, B.; Kim, K.; Cortis, C.; Friesner, R. A.; Murphy, R. B.; Ringnalda, M. N.; Sitkoff, D.; Honig, B. J. Phys. Chem. 1996, 100, 11775-11788.
14. Chen, W.; Gordon, M. S. J. Chem. Phys. 1996, 105, 11081-11090.
15. Bader, J. S.; Cortis, C. M.; Berne, B. J. J. Chem. Phys. 1997, 106, 2372-2387.
16. (a) Giesen, D. J.; Gu, M. Z.; Cramer, C. J.; Truhlar, D. G. J. Org. Chem. 1996, 61, 8720-8721.
17. (b) Chambers, C. C.; Hawkins, G. D.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. 1996, 100, 16385-16398.
18. Hummer, G.; Pratt, L. R.; García, A. E. J. Am. Chem. Soc. 1997, 119, 8523-8527.
19. Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127-6129.
20. Truong, T. N.; Stefanovich, E. V. J. Phys. Chem. 1995, 99, 14700-14706. Truong, T. N.; Truong, T.-T. T.; Stefanovich, E. V. J. Phys. Chem. 1997, 107, 11881-1889.
21. Truong, T. N.; Stefanovich, E. V. J. Phys. Chem. 1995, 99, 14700- 14706. Truong, T. N.; Truong, T.-T. T.; Stefanovich, E. V. J. Phys. Chem. 1997, 107, 11881-1889.
22. (a) Edinger, S. R.; Cortis, C.; Shenkin, P. S.; Friesner, R. A. J. Phys. Chem. B 1997, 101, 1190-1197.
23. (b) Luo, H. Q.; Tucker, S. C. J. Phys. Chem. B 1997, 101, 1063-1071.
24. (c) Alagona, G.; Ghio, C.; Nagy, P. I.; Durant, G. J. J. Phys. Chem. 1994, 98, 5422-5430.
25. (d) Best, S. A.; Merz, K. M.; Reynolds, C. H. J. Phys. Chem. B 1997, 101, 10479-10487.
26. (e) Harris, N. J.; Ohwada, T.; Lammertsa, K. J. Comput. Chem. 1998, 19, 250-257.
27. (f) Elcock, A. H.; McCammon, J. A. J. Phys. Chem. B 1997, 101, 9624-9634.
28. Allen, M. P.; Tildesley, D. J. Computer Simulations of Liquids; Clarendon Press: Oxford, UK, 1987.
29. (a) Denti, T. Z. M.; van Gunsteren, W. F.; Diederich, F. J. Am. Chem. Soc. 1996, 118, 6044-6051.
30. (b) Jorgensen, W. L.; Nguyen, T. B. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 1194-1200.
31. (a) Tirado-Rives, J.; Jorgensen, W. L. Biochemistry 1997, 36, 7313-7329.
32. (b) Humphreys, D. D.; Friesner, R. A.; Berne, B. J. J. Phys. Chem. 1995, 99, 10674-10685.
33. (c) Schiffer, C. A.; Dötsch, V.; Wütrich, K.; van Gunsteren, W. F. Biochemistry 1995, 34, 15057-15067.
34. (a) Perrin, C. L.; Fabian, M. A.; Rivero, I. A. J. Am. Chem. Soc. 1998, 120, 1044-1047.
35. (b) Nagy, P. I.; Takäcs-Noväk, K. J. Am. Chem. Soc. 1997, 119, 4999-5006.
36. (c) Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Am. Chem. Soc. 1992, 114, 1645-1652.
37. (d) Wiberg, K. B.; Wong, M. W. J. Am. Chem. Soc. 1993, 115, 1078-1084.
38. (e) Wiberg, K. B.; Marquez, M. M. J. Am. Chem. Soc. 1994, 116, 2197-2198.
39. (f) Jorgensen, W. L.; Morales de Tirado, P. I.; Severance, D. L. J. Am. Chem. Soc. 1994, 116, 2199-2200.
40. (a) Wiberg, K. B.; Keith, T. A.; Frisch, M. J.; Murcko, M. J. Phys. Chem. 1995, 99, 9072-9079.
41. (b) Foresman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonian, J.; Frisch, M. J. J. Phys. Chem. 1996, 100, 16098-16104.
42. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd ed.; VCH Publishers: Germany, 1988.
43. (a) Stewart, W. E.; Siddall, T. H., III Chem. Rev. 1970, 70, 517-551 and references therein.
44. (b) Drakenberg, T.; Dahlqvist, K. J.; Forsen, S. J. Phys. Chem. 1972, 76, 2178-2183.
45. Wiberg, K. B.; Rablen, P. R.; Rush, D. J.; Keith, T. A. J. Am. Chem. Soc. 1995, 117, 4261-4270.
46. (a) Cox, C.; Young, V. G., Jr.; Lectka, T. J. Am. Chem. Soc. 1997, 119, 2307-2308.
47. (b) Cox, C.; Ferraris, D.; Murthy, N. N.; Lectka, T. J. Am. Chem. Soc. 1996, 118, 5332-5333.
48. Chiara, J. L.; Gómez-Sànchez, A.; Bellanato, J. J. Chem. Soc., Perkin Trans. 2 1992, 787-798.
49. Suarez, C.; LeMaster, C. B.; LeMaster, C. L.; Tafazzoli, M.; True, N. S. J. Phys. Chem. 1990, 94, 6679-6683.
50. Duffy, E. M.; Severance, D. L.; Jorgensen, W. L. J. Am. Chem. Soc. 1992, 114, 7535-7542.
51. Gao, J. J. Am. Chem. Soc. 1993, 115, 2930-2935. Gao, J. Proc. Indian Acad. Sci. 1994, 106, 507.
52. Gao, J. J. Am. Chem. Soc. 1993, 115, 2930-2935. Gao, J. Proc. Indian Acad. Sci. 1994, 106, 507.
53. (a) Ross, B. D.; True, N. S. J. Am. Chem. Soc. 1984, 106, 2451-2452. Cf. LeMaster, C. B.; True, N. S. J. Phys. Chem. 1989, 93, 1307- 1311.
54. (a) Ross, B. D.; True, N. S. J. Am. Chem. Soc. 1984, 106, 2451- 2452. Cf. LeMaster, C. B.; True, N. S. J. Phys. Chem. 1989, 93, 1307-1311.
55. (b) Ross, B. D.; True, N. S.; Matson, G. B. J. Phys. Chem. 1984, 88, 2675-2678.
56. (c) Feigel, M. J. Chem. Soc. Chem. Commun. 1980, 456-457.
57. ‡ values reported in (c) and (d) were based on a transmission coefficient of 1.0, and were recalculated using 0.5 to be consistent with the values given in (a) and (b) and the values reported in the current work.
58. (a) Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. J. Chem. Phys. 1991, 94, 7221-7230.
59. (b) Curtiss, L. A.; Carpenter, J. E.; Raghavachari, K.; Pople, J. A. J. Chem. Phys. 1992, 96, 9030-9034.
60. Previous paper in this issue: Rablen, P. R.; Miller, D. A.; Bullock, V. R.; Hutchinson, P. H.; Gorman, J. A. J. Am. Chem. Soc. 1999, 121, 218-226.
61. Onsager, L. J. Am. Chem. Soc. 1936, 58, 1486-1493. Kirkwood, J. G. J. Chem. Phys. 1934, 2, 351-361. Bornx M. Z. Phys. 1920, 1, 45- 48.
62. Onsager, L. J. Am. Chem. Soc. 1936, 58, 1486-1493. Kirkwood, J. G. J. Chem. Phys. 1934, 2, 351-361. Bornx M. Z. Phys. 1920, 1, 45- 48.
63. Onsager, L. J. Am. Chem. Soc. 1936, 58, 1486-1493. Kirkwood, J. G. J. Chem. Phys. 1934, 2, 351-361. Bornx M. Z. Phys. 1920, 1, 45-48.
64. (a) Tapia, O.; Goscinski, O. Mol. Phys. 1975, 29, 1653-1661.
65. (b) Rivail, J. L.; Terryn, B.; Ruiz-López, M. F. J. Mol. Struct.: THEOCHEM 1985, 120, 387.
66. Cf.: Wong, M. W.; Frisch, M. J.; Wiberg, K. B. J. Am. Chem. Soc. 1991, 113, 4776-4782. Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Chem. Phys. 1991, 95, 8991-8998.
67. Cf.: Wong, M. W.; Frisch, M. J.; Wiberg, K. B. J. Am. Chem. Soc. 1991, 113, 4776-4782. Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Chem. Phys. 1991, 95, 8991-8998.
68. Rinaldi, D.; Ruiz-Lopez, M. F.; Rivail, J.-L. J. Chem. Phys. 1983, 78, 834-838.
69. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys, 1981, 55, 117. Tomasi, J.; Bonaccorsi, R.; Cammi, R.; Valle, F. O. J. J. Mol. Struct. 1991, 234, 401.
70. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys, 1981, 55, 117. Tomasi, J.; Bonaccorsi, R.; Cammi, R.; Valle, F. O. J. J. Mol. Struct. 1991, 234, 401.
71. Clifford, S.; Keith, T. A.; Frisch, M. J. To be submitted for publication.
72. Jorgensen, W. L. BOSS, Version 3.6; Yale University: New Haven, CT, 1996.
73. Carlson, H. A.; Nguyen, T. B.; Orozco, M.; Jorgensen, W. L. J. Comput. Chem. 1993, 14, 1240-1249.
74. Recent examples: (a) Fox, T.; Scanlan, T. S.; Kollman, P. A. J. Am. Chem. Soc. 1997, 119, 11571-11577. (b) Peräkylä, M.; Kollman, P. A. J. Am. Chem. Soc. 1997, 119, 1189-1196. (c) Kirchhoff, P. D.; Bass, M. B.; Hanks, B. A.; Griggs, J. M.; Collet, A.; McCammon, J. A. J. Am. Chem. Soc. 1996, 118, 3237-3246.
75. Recent examples: (a) Fox, T.; Scanlan, T. S.; Kollman, P. A. J. Am. Chem. Soc. 1997, 119, 11571-11577. (b) Peräkylä, M.; Kollman, P. A. J. Am. Chem. Soc. 1997, 119, 1189-1196. (c) Kirchhoff, P. D.; Bass, M. B.; Hanks, B. A.; Griggs, J. M.; Collet, A.; McCammon, J. A. J. Am. Chem. Soc. 1996, 118, 3237-3246.
76. Recent examples: (a) Fox, T.; Scanlan, T. S.; Kollman, P. A. J. Am. Chem. Soc. 1997, 119, 11571-11577. (b) Peräkylä, M.; Kollman, P. A. J. Am. Chem. Soc. 1997, 119, 1189-1196. (c) Kirchhoff, P. D.; Bass, M. B.; Hanks, B. A.; Griggs, J. M.; Collet, A.; McCammon, J. A. J. Am. Chem. Soc. 1996, 118, 3237-3246.
77. (a) Jorgensen, W. L.; Maxwell, D. S.; Tirado-Rives, J. J. Am. Chem. Soc. 1996, 118, 11225-11236.
78. (b) Jorgensen, W. L.; Tirado-Rives, J. J. Am. Chem. Soc. 1988, 110, 1657-1666.
79. (c) Jorgensen, W. L.; Swenson, C. J. J. Am. Chem. Soc. 1985, 107, 569-578.
80. (d) Jorgensen, W. L.; Swenson, C. J. J. Am. Chem. Soc. 1985, 107, 1489-1496.
81. Rablen, P. R.; Lockman, J. W.; Jorgensen, W. L. J. Phys. Chem. 1998, 102, 3782-3797.
82. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
83. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J. D.; Impey, R. W.; Klein, M. L. J. Chem. Phys. 1983, 79, 926-935.
84. Jorgensen et al. J. Phys. Chem. 1986, 90, 1276-1284.
85. Jorgensen, W. L.; Briggs, J. M. Mol. Phys. 1988, 63, 547-558.
86. Jorgensen, W. L.; Madura, J. D.; Swenson, C. J. J. Am. Chem. Soc. 1984, 106, 6638-6646.
87. (a) Perng, B.-C.; Newton, M. D.; Raineri, F. O.; Friedman, H. L. J. Chem. Phys. 1996, 104, 7153-7176.
88. (b) Perng, B.-C.; Newton, M. D.; Rainen, F. O.; Friedman, H. L. J. Chem. Phys. 1996, 104, 7177-7204.
89. It is worthy of note that the data point for acetonitrile in Figure 2 lies somewhat above the best fit line, indicating a higher barrier than in other solvents having comparable values for the Onsager dielectric function. This deviation possibly indicates that acetonitrile, like the aromatic and chlorinated solvents, yields somewhat stronger than expected interactions with polar solutes due to unusually great electronic polarizability. The "soft" π-system of acetonitrile could certainly account for such polarizability. A similar pattern was observed with DMA and DMF previously, where again acetonitrile yielded a somewhat stronger solvent effect than did acetone.
90. The default value for this parameter in the Gaussian 94 code is in fact 0.001 electrons per cubic Bohr, not 0.0004. Use of the larger contour would probably also improve the calculated results for DMA.
91. Jorgensen, W. L.; McDonald, N. A.; Selmi, M.; Rablen, P. R. J. Am. Chem. Soc. 1995, 117, 11809-11810.
92. Wiberg, K. B.; Rablen, P. R. J. Am. Chem. Soc. 1995, 117, 2201-2209.
93. Waldeck, D. H. J. Mol. Liq. 1993, 57, 127-148.
94. Waldeck, D. H. Chem. Rev. 1991, 91, 415-436.
95. Park, N. S.; Waldeck, D. H. J. Phys. Chem. 1990, 94, 662-669.
96. Zeglinski, D. M.; Waldeck, D. H. J. Phys. Chem. 1988, 92, 692-701.
97. (a) Alavi, D. S.; Waldeck, D. H. J. Chem. Phys. 1991, 94, 6196-6202.
98. (b) Alavi, D. S.; Hartman, R. S.; Waldeck, D. H. J. Chem. Phys. 1991, 94, 4509-4520.
99. Marconcelli, M.; Maclnnis, J.; Fleming, G. R. Science 1989, 243, 1674-1681.
100. The one partial exception to this statement is the set of Monte Carlo simulations in TIP4P water, where the experimentally determined solvent effect is underestimated by only about 0.6 kcal/mol.
101. If electronic polarization terms are explicitly incorporated into the potential functions, then it is of course possible to treat nonpolar solvents correctly, but the cost in computer time is generally very high.
102. 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.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94 (Revision C.2); Gaussian, Inc., Pittsburgh, PA, 1995.
103. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
104. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
105. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
106. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200-206.
107. (a) Breneman, C. M.; Wiberg, K. B. J. Comput. Chem. 11, 1990, 361.
108. (b) Chirlian, L. E.; Francl, M. M. J. Comput. Chem. 1987, 8, 894.
109. Jorgensen, W. L.; Buckner, J. K. J. Phys. Chem. 1987, 91, 6083-6085. Jorgensen, W. L.; Gao, J. J. Am. Chem. Soc. 1988, 110, 4212-4216.
110. Jorgensen, W. L.; Buckner, J. K. J. Phys. Chem. 1987, 91, 6083- 6085. Jorgensen, W. L.; Gao, J. J. Am. Chem. Soc. 1988, 110, 4212-4216.