Further quantum mechanical evidence that difluorotoluene does not hydrogen bond

Journal of Physical Chemistry B

Volumn 105, Issue 35, 2001, Pages 8445-8451

  Sherer, Edward C ^b   Bono, Sam J ^a   Shields, George C ^a  

^a HAMILTON COLLEGE   (United States)

^b University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SOLVATION;

CHEMICAL RELAXATION; DISSOCIATION; GIBBS FREE ENERGY; HYDROGEN BONDS; MONOMERS; PROBABILITY DENSITY FUNCTION; QUANTUM THEORY; TOLUENE; WATER;

DNA;

EID: 0035818099     PISSN: 10895647     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp010197x     Document Type: Article

References (81)

1. Watson, J.; Crick, H.C. Nature 1953, 171, 737-738.
2. Kutcha, R.D.; Mizrahi, V.; Benkovic, P.A.; Johnson, K.A.; Benkovic, S.J. Biochemistry 1987, 26, 6,.
3. Sloane, D.L.; Goodman, M.F. Nucl. Acids Res. 1988, 16, 6465-6475.
4. Echols, H.; Goodman, M.F. Annu. Rev. Biochem. 1991, 60, 477-511.
5. Diederichsen, U. Angew. Chem., Int. Ed. Engl. 1998, 37, 1655-1657.
6. Goodman, M.F. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 10493-10495.
7. Kool, E. Biopolymers 1998, 48, 3-17.
8. Moran, S.; Ren, R.X.-F.; Kool, E.T. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 10506-10511.
9. Moran, S.; Ren, R.X.-F.; Rumney S. IV; Kool, E.T. J. Am. Chem. Soc. 1997, 119, 2056-2057.
10. Guckian, K.M.; Kool, E.T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2825-2828.
11. Guckian, K.M.; Schweitzer, B.A.; Ren, R.X.-F.; Sheils, C.J.; Paris, P.L.; Tahmassebi, D.C.; Kool, E.T. J. Am. Chem. Soc. 1996, 118, 8182-8183.
12. Guckian, K.M.; Morales, J.C.; Kool, E.T. J. Org. Chem. 1998, 63, 3, 9652-9656.
13. Guckian, K.M.; Krugh, T.R.; Kool, E.T. Nat. Struct. Biol. 1998, 5, 954-959.
14. Matray, T.J.; Kool, E.T. J. Am. Chem. Soc. 1998, 120, 6191-6192.
15. Liu, D.; Moran, S.; Kool, E.T. Chem. Biol. 1997, 4, 919-926.
16. Kool, E.T.; Morales, J.C.; Guckian, K.M. Angew. Chem., Int. Ed. Engl. 2000, 39.
17. Schmidt, K.S.; Sigel, R.K.; Filippov, D.V.; van der Marel, G.A.; Lippert, B.; Reedijk, J. New J. Chem. 2000, 24, 195-197.
18. Barsky, D.; Kool, E.T.; Colvin, M.E. J. Biomol. Struct. Dyn. 1999, 16, 1119-1134.
19. Berger, M.; Ogawa, A.K.; McMinn, D.L.; Wu, Y.; Schultz, P.G.; Romesberg, F.E. Angew. Chem., Int. Ed. Engl. 2000, 39, 2940-2942.
20. Ogawa, A.K.; Wu, Y.; Berger, M.; Schultz, P.G.; Romesberg, F.E. J. Am. Chem. Soc. 2000, 122, 8803-8804.
21. Morales, J.C.; Kool, E.T. Nat. Struct. Biol. 1998, 5, 950-954.
22. Guckian, K.M.; Krugh, T.R.; Kool, E.T. J. Am. Chem. Soc. 2000, 122, 6841-6847.
23. Florian, J.; Goodman, B.F.; Warshel, A. J. Phys. Chem. B 2000, 104, 10092-10099.
24. Morales, J.C.; Kool, E.T. Biochemistry 2000, 39, 2626-2632.
25. Cubero, E.; Sherer, E.C.; Luque, F.J.; Orozco, M.; Laughton, C.A. J. Am. Chem. Soc. 1999, 121, 8653-8654.
26. Cubero, E.; Laughton, C.A.; Luque, F.J.; Orozco, M. J. Am. Chem. Soc. 2000, 122, 6891-6899.
27. Hobza, P.; Sponer, J. Chem. Rep. 1999, 99, 3247-3276.
28. Meyer, M.; Suhnel, J. J. Biomol. Struct. Dyn. 1997, 15, 619-624.
29. Santhosh, C.; Mishra, P.C. Int. J. Quantum Chem. 1998, 68, 351-355.
30. Wang, X.; Houk, K.N. Chem. Commun. 1998, 2631-2632.
31. Evans, T.A.; Seddon, K.R. Chem. Commun. 1997, 2023-2024.
32. Cieplak, P.; Kollman, P.A. J. Am. Chem. Soc. 1988, 110, 3734-3739.
33. Spartan5.0. Wavefunction, Inc., 18401 Von Karman Ave., Ste. 370, Irvine, CA 92612, U.S.A.
34. Hehre, W.J.; Radom, L.; Schleyer, P.v.R.; Pople, J.A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
35. Hehre, W.J.; Ditchfield, R.; Pople, J.A. J. Chem. Phys. 1972, 56, 2257-2261.
36. Hariharan, P.C.; Pople, J.A. Chem. Phys. Lett. 1972, 66, 217.
37. Ditchfield, R.; Hehre, W.J.; Pople, J.A. J. Chem. Phys. 1971, 54, 724-728.
38. Becke, A.D. J. Chem. Phys. 1996, 104, 1040-1046.
39. Lee, C.; Yang, W.; Parr, R.G. Phys. Rev. B 1988, 37, 785.
40. Miehlich, A.; Savin, A.; Stoll, H.; Pruess, H. Chem. Phys. Lett. 1989, 157, 200.
41. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Gill, P.M.W.; Johnson, B.G.; Robb, M.A.; Cheeseman, J.R.; Keith, T.A.; Petersson, G.A.; Montgomery, J.A.; Raghavachari, K.; Al-Laham, M.A.; Zakrzewski, V.G.; Ortiz, J.V.; Foresman, J.B.; Peng, C.Y.; Ayala, P.A.; Wong, M.W.; Andres, J.L.; Replogle, E.S.; Gomperts, R.; 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 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
42. Scott, A.P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.
43. Xantheas, S.S. J. Chem. Phys. 1996, 104, 8821-8824.
44. Paizs, B.; Suhai, S. J. Comput. Chem. 1998, 19, 575-584.
45. Halász, G.J.; Vibók, Á.; Mayer, I. J. Comput. Chem. 1999, 20, 274-283.
46. Hawkins, G.D.; Giesen, D.J.; Lynch, G.C.; Chambers, C.C.; Rossi, I.; Storer, J.W.; Li, J.; Winget, P.; Rinaldi, D.; Liotard, D.A.; Cramer, C.J.; Truhlar, D.G. Based in part on AMPAC-version 2.1 by D.A. Liotard, E.F. Healy, J.M. Ruiz, and M.J.S. Dewar. 1999. AMSOL-version 6.6. University of Minnesota, Minneapolis.
47. Giesen, D.J.; Chambers, C.C.; Cramer, C.J.; Truhlar, D.G. J. Phys. Chem. B 1997, 101, 5084-5088.
48. Eksterowitcz, J.E.; Miller, J.L.; Kollman, P.A. J. Phys. Chem. B 1997, 101, 10971-10975.
49. Li, J.; Cramer, C.J.; Truhlar, D.G. Biophys. Chem. 1999, 78, 147-155.
50. Stewart, J.J.P. J. Comput. Chem. 1989, 10, 221-264.
51. Sherer, E.C.; Cramer, C.J. J. Comput. Chem. 2001, 22, 1167-1179.
52. Sponer, J.; Hobza, P. J. Phys. Chem. 2000, 104, 4592-4597.
53. Brameld, K.; Dasgupta, S.; Goddard, W.A., III. J. Phys. Chem. B 1997, 101, 4851-4859.
54. Yanson, I.K.; Teplitsky, A.B.; Sukhodub, L.F. Biopolymers 1979, 18, 1149-1170.
55. Hobza, P.; Sponer, J. Chem. Phys. Lett. 1996, 261, 379-384.
56. Florian, J.; Sponer, J,; Warshel, A. J. Phys. Chem. B 1999, 103, 884-892.
57. Young, M.; Jayaram, B.; Beveridge, D. J. Phys. Chem. B 1998, 102, 7666-7669.
58. Arora, N.; Jayaram, B. J. Phys. Chem. B 1998, 102, 6139-6144.
59. Kyogoku, K.; Lord, R.C.; Rich, A. Proc. Natl. Acad. sci. U.S.A. 1967, 57, 250-257.
60. Kyogoku, Y.; Lord, R.C.; Rich, A. Science 1966, 154, 518-520.
61. Binford J.S. Jr.; Holloway, D.M. J. Mol. Biol. 1968, 31, 91-99.
62. Kratochvil, M.; Sponer, J.; Hobza, P. J. Am. Chem. Soc. 2000, 122, 3495-3499.
63. Solie, T.N.; Schellman, J.A. J. Mol. Biol. 1968, 33, 61-77.
64. Katz, L.; Penman, S. J. Mol. Biol. 1966, 15, 220-231.
65. Hamlin, R.M.; Lord, R.C.; Rich, A. Science 1965, 148, 1734.
66. Miller, J.H.; Sobell, H.M. J. Mol. Biol. 1967, 24, 345-350.
67. Norberg, J.; Nilsson, L. Biophys. J. 1998, 74, 394-402.
68. Jurema, M.W.; Shields, G.C. J. Comput. Chem. 1993, 14, 89-104.
69. Lively, T.N.; Jurema, M.W.; Shields, G.C. Int. J. Quantum Chem., Quantum Biol. Symp. 1994, 21, 95-107.
70. Hobza, P.; Kabelác, M.; Sponer, J.; Mejzlík, P.; Vondrásek, J. J. Comput. Chem. 1997, 18, 1136-1150.
71. Elstner, M.; Hobza, P.; Frauenheim, T.; Suhai, S.; Kaxiras, E. J. Chem. Phys. 2001, 114, 5149-5155.
72. Kurita, N.; Araki, M.; Nakao, K.; Kobayashi, K. Int. J. Quantum Chem. 2000, 76, 677-685.
73. Kurita, N.; Kobayashi, K. Comput. Chem. 2000, 24, 351-357.
74. Kiefer, J.R.; Mao, C.; Braman, J.C.; Beese, L.S. Nature 1998, 391, 304-307.
75. Pelletier, H.; Sawaya, M.R.; Kumar, A.; Wilson, S.H.; Kraut, J. Science 1994, 264, 1891-1903.
76. Eom, S.H.; Wang, J.; Steitz, T.A. Nature 1996, 382, 278-281.
77. Beard, W.A.; Wilson, S.H. Chem. Biol. 1998, 5, R7-R13.
78. Doublie, S.; Tabor, S.; Long, A.M.; Richardson, C.C.; Ellenberger, T. Nature 1998, 391, 251-258.
79. Johnson, K.A. Annu. Rev. Biochem. 1993, 62, 685-713.
80. (80) Morales, J.C.; Kool, E.T. J. Am. Chem. Soc. 2000, 122, 1001-1007.
81. Morales, J.C.; Kool, E.T. J. Am. Chem. Soc. 1999, 121, 2323-2324.