Exo-anomeric effects on energies and geometries of different conformations of glucose and related systems in the gas phase and aqueous solution

Carbohydrate Research

Volumn 298, Issue 1-2, 1997, Pages 1-14

  Cramer, Christopher J ^a   Truhlar, Donald G ^a   French, Alfred D ^b  

^a University of Minnesota   (United States)

^b AGRICULTURAL RESEARCH SERVICE   (United States)

Author keywords

Conformational analysis; exo Anomeric effect; Hyperconjugation; Solvation

Indexed keywords

GLUCOSE; TETRAHYDROPYRAN DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CALCULATION; CARBOHYDRATE ANALYSIS; CONFORMATION; CONJUGATION; ENERGY; GEOMETRY; PHYSICAL PHASE; PRIORITY JOURNAL; SOLVATION;

EID: 0031044316     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(96)00297-2     Document Type: Article

References (70)

1. C.L. Jungius, Z. Phys. Chem., 52 (1905) 97-108.
2. R.U. Lemieux, in P. de Mayo (Ed.), Molecular Rearrangements, Interscience, New York, 1964, pp 709-769.
3. C.G. Pearson and O. Rumquist, J. Org. Chem., 33 (1968) 2572-2574.
4. A.J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer-Verlag, Berlin, 1983.
5. I. Tvaroška and T. Bleha, Adv. Carbohydr. Chem. Biochem., 47 (1989) 45-123.
6. G.R.J. Thatcher (Ed.), The Anomeric Effect and Associated Stereoelectronic Effects, ACS Symposium Series 539, American Chemical Society, Washington, DC, 1993.
7. P.P. Graczyk and M. Mikolajczyk, in E.L. Eliel and S.H. Wilen (Eds.), Topics in Stereochemistry, Vol. 21, John Wiley & Sons, New York, 1994, pp 159-349.
8. J.T. Edward, Chem. Ind. (London), (1955) 1102-1104.
9. C.B. Anderson and D.T. Sepp, Tetrahedron, 24 (1968) 1707-1715.
10. V.G.S. Box, Heterocycles, 31 (1990) 1157-1181.
11. C. Romers, C. Altona, H.R. Buys, and E. Havinga, Top. Stereochem., 4 (1969) 39-97.
12. G.A. Jeffrey, J.A. Pople, and L. Radom, Carbohydr. Res., 25 (1972) 117-131.
13. S. Wolfe, M.-H. Whangbo, and D.J. Mitchell, Carbohydr. Res., 69 (1979) 1-26.
14. G.A. Jeffrey and J.H. Yates, Carbohydr. Res., 96 (1981) 205-213.
15. K.B. Wiberg and M.A. Murcko, J. Am. Chem. Soc., 111 (1989) 4821-4828.
16. M.C. Krol, C.J.M. Huige, and C. Altona, J. Comp. Chem., 11 (1990) 765-790.
17. C.J. Cramer, J. Org. Chem., 57 (1992) 7034-7043.
18. E. Juaristi and G. Cuevas, Tetrahedron, 48 (1992) 5019-5087.
19. P.A. Petillo and L.E. Lerner, in G.R.J. Thatcher (Ed.), The Anomeric Effect and Related Stereoelectronic Effects, ACS Symposium Series 539, American Chemical Society, Washington, DC, 1993, pp 156-175.
20. U. Salzner and P.V.R. Schleyer, J. Am. Chem. Soc., 115 (1993) 10231-10236.
21. I. Tvaroška and J.P. Carver, J. Phys. Chem., 98 (1994) 9477-9485.
22. U. Salzner and P.v.R. Schleyer, J. Org. Chem., 59 (1994) 2138-2155.
23. J.R. Kneisler and N.L. Allinger, J. Comp. Chem., 17 (1996) 757-766.
24. I. Tvaroška and T. Kožár, J. Am. Chem. Soc., 102 (1980) 6929-6936.
25. I. Tvaroška and T. Kožár, Int. J. Quant. Chem., 23 (1983) 765-778.
26. J.-P. Praly and R.U. Lemieux, Can. J. Chem., 65 (1987) 213-223.
27. R. Montagnani and J. Tomasi, Int. J. Quant. Chem., 39 (1991) 851-870.
28. S. Ha, J. Gao, B. Tidor, J.W. Brady, and M. Karplus, J. Am. Chem. Soc., 113 (1991) 1553-1557.
29. O. Kysel and P. Mach, J. Mol. Struct. (Theochem), 227 (1991) 285-293.
30. C.J. Cramer and D.G. Truhlar, J. Am. Chem. Soc., 115 (1993) 5745-5753.
31. B.P. van Eijck, R.W.W. Hooft, and J. Kroon, J. Phys. Chem., 97 (1993) 12093-12099.
32. C.L. Perrin and K.B. Armstrong, J. Am. Chem. Soc., 115 (1993) 6825-6834.
33. K.B. Wiberg and M. Marquez, J. Am. Chem. Soc., 116 (1994) 2197-2198.
34. W.L. Jorgensen, P.I.M. Detirado, and D.L. Severance, J. Am. Chem. Soc., 116 (1994) 2199-2200.
35. C.L. Perrin, K.B. Armstrong, and M.A. Fabian, J. Am. Chem. Soc., 116 (1994) 715-722.
36. E.S. Marcos, R.R. Pappalardo, J.L. Chiara, M.C. Domene, J.M. Martínez, and R.M. Parrondo, J. Mol. Struct. (Theochem), in press.
37. L. Schliefer, H. Senderowitz, P. Aped, E. Tartakovsky, and B. Fuchs, Carbohydr. Res., 206 (1990) 21-39.
38. W.J. Hehre, L. Radom, P.v.R. Schleyer, and J.A. Pople, Ab Initio Molecular Orbital Theory, Wiley, New York, 1986.
39. T.H. Dunning, J. Chem. Phys., 90 (1989) 1007-1023.
40. S.E. Barrows, F.J. Dulles, C.J. Cramer, D.G. Truhlar, and A.D. French, Carbohydr. Res., 276 (1995) 219-251.
41. S.E. Barrows, J.W. Storer, C.J. Cramer, D.G. Truhlar, G. Johnson, and A.D. French, to be published.
42. A.E. Reed, F. Weinhold, L.A. Curtiss, and D.J. Pochatko, J. Chem. Phys., 84 (1986) 5687-5705.
43. I.J.-H. Lii and N.L. Allinger, J. Phys. Org. Chem., 7 (1994) 591-609.
44. N.L. Allinger and L. Yan, J. Am. Chem. Soc., 115 (1993) 11918-11925.
45. A.D. French, L. Schäfer, and S.Q. Newton, Carbohydr. Res., 239 (1993) 51-60.
46. A.D. French and M.K. Dowd, J. Comp. Chem., 15 (1994) 561-570.
47. N.L. Allinger, X.F. Zhou, and J. Bergsma, J. Mol. Struct. (Theochem), 118 (1994) 69-83.
48. C. Van Alsenoy, A.D. French, M. Cao, S.Q. Newton, and L. Schäfer, J. Am. Chem. Soc., 116 (1994) 9590-9595.
49. M.K. Dowd, A.D. French, and P.J. Reilly, Carbohydr. Res., 264 (1994) 1-19.
50. C.C. Chambers, G.D. Hawkins, C.J. Cramer, and D.G. Truhlar, J. Phys. Chem., 100 (1996) 16385-16398.
51. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, and J.J.P. Stewart, J. Am. Chem. Soc., 107 (1985) 3902-3909.
52. J.W. Storer, D.J. Giesen, C.J. Cramer, and D.G. Truhlar, J. Comput.-Aid. Mol. Des., 9 (1995) 87-110.
53. J.W. Storer, D.J. Giesen, G.D. Hawkins, G.C. Lynch, C.J. Cramer, D.G. Truhlar, and D.A. Liotard, in C.J. Cramer and D.G. Truhlar (Eds.), Structure and Reactivity in Aqueous Solution, ACS Symposium Series 568, American Chemical Society, Washington, DC, 1994, pp 24-49.
54. D.A. Liotard, G.D. Hawkins, G.C. Lynch, C.J. Cramer, and D.G. Truhlar, J. Comp. Chem., 16 (1995) 422-440.
55. C.J. Cramer and D.G. Truhlar, Chem. Phys. Lett., 198 (1992) 74-80; 202 (1993) 1567(E).
56. C.J. Cramer and D.G. Truhlar, Chem. Phys. Lett., 198 (1992) 74-80; 202 (1993) 1567(E).
57. M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Cioslowski, B.B. Stefanov, A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, M.W. Wong, J.L. Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. DeFrees, J. Baker, J.P. Stewart, M. Head-Gordon, C. Gonzalez, and J.A. Pople, GAUSSIAN94 RevD.1, GAUSSIAN Inc., Pittsburgh, PA, 1995.
58. E.D. Glendening, J.E. Carpenter, and F. Weinhold, NBO version 3.1, University of Wisconsin, Madison, WI, 1995.
59. G.D. Hawkins, G.C. Lynch, D.J. Giesen, I. Rossi, J.W. Storer, D.A. Liotard, C.J. Cramer, and D.G. Truhlar, QCPE Bull., 16 (1996) 11-13.
60. C.J. Cramer and D.G. Truhlar, J. Am. Chem. Soc., 113 (1991) 8305-8315, 9901(E).
61. C.J. Cramer and D.G. Truhlar, in O. Tapia and J. Bertrán (Eds.), Solvent Effects and Chemical Reactivity, Kluwer, Dordrecht, 1996, pp. 1-81.
62. C.J. Cramer and D.G. Truhlar, J. Am. Chem. Soc., 113 (1991) 8552-8553 9901(E).
63. W.L. Jorgensen and J. Tirado-Rives, J. Am. Chem. Soc., 110 (1988) 1657-1666.
64. W.L. Jorgensen, J. Chandrasekhar, J.D. Madura, R.W. Impey, and M.L. Klein, J. Chem. Phys., 79 (1983) 926-935.
65. I. Tvaroška, Biopolymers, 21 (1982) 1887-1897.
66. C.J. Cramer, unpublished calculations.
67. C.J. Cramer and D.G. Truhlar, J. Am. Chem. Soc., 116 (1994) 3892-3900.
68. S.E. Barrows, C.J. Cramer, D.G. Truhlar, E.J. Weber, and M.S. Elovitz, Environ. Sci. Technol., in press.
69. W.F. van Gunsteren and H.J.C. Berendsen, Groningen Molecular Simulation (GROMOS) Library Manual, BIOMOS, Nijenbourgh 16, Groningen, The Netherlands, 1987.
70. K.-H. Ott and B. Meyer. J. Comp. Chem., 17 (1996) 1068-1084.