Alcohols, ethers, carbohydrates, and related compounds. IV. Carbohydrates

Journal of Computational Chemistry

Volumn 24, Issue 12, 2003, Pages 1504-1513

  Lii, Jenn Huei ^a   Chen, Kuo Hsiang ^a   Allinger, Norman L ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

Carbohydrates; Delta 2 effect; Molecular mechanics

Indexed keywords

ALCOHOLS; CALCULATIONS; CARBOHYDRATES; CONFORMATIONS; ETHERS; ETHYLENE; GLYCOLS; HYDROGEN BONDS; MOLECULES; QUANTUM THEORY;

AB INITIO CALCULATIONS; FURANOSE; GAS PHASE ANOMERIC EFFECT; HEXOSES; MOLECULAR MECHANICS; PYRANOSE;

MOLECULAR DYNAMICS;

ALCOHOL DERIVATIVE; CARBOHYDRATE; ETHER DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; MATHEMATICAL COMPUTING; QUANTUM THEORY; THERMODYNAMICS;

ALCOHOLS; CARBOHYDRATES; ETHERS; MATHEMATICAL COMPUTING; MODELS, MOLECULAR; MOLECULAR CONFORMATION; QUANTUM THEORY; THERMODYNAMICS;

EID: 0043062724     PISSN: 01928651     EISSN: None     Source Type: Journal    
DOI: 10.1002/jcc.10271     Document Type: Article

References (43)

1. Angyal, S. J. Aust J Chem 1968, 21, 2737.
2. Brady, J. W. J Am Chem Soc 1989, 111, 5155.
3. Ha, S.; Gao, J.; Tidor, B.; Brady, J. W.; Karplus, M. J Am Chem Soc 1991, 113, 1553.
4. (a) Polavarapu, P. L.; Ewig, C. S. J Comput Chem 1992, 13, 1255
5. (b) Zheng, Y.-J.; LeGrand, S. M.; Merz, K. M. J Comput Chem 1992, 13, 1151.
6. (a) Cramer, C. J.; Truhlar, D. G. J Am Chem Soc 1993, 115, 5745
7. (b) Glennon, T. M.; Zheng, Y.-J.; LeGrand, S. M.; Shutzberg, B. A.; Merz, K. M. J Comput Chem 1994, 9, 1019.
8. (a) Barrows, S. E.; Dulles, F. J.; Cramer, C. J.; French, A. D.; Truhlar, D. G. Carbohydr Res 1995, 276, 219
9. (b) Woods, R. J.; Raymond, A. D.; Edge, C. J. J Phys Chem 1995, 99, 3821
10. (c) Senderowitz, H.; Parish, C.; Still, W. C. J Am Chem Soc 1996, 118, 2078
11. (d) Reiding, S.; Schlenkrich, M.; Brickmann, J. J Comput Chem 1996, 17, 450
12. (e) Ott, K.-H.; Meyer, B. J Comput Chem 1996, 17, 1068
13. (f) Frontera, A.; Tiradorives, J.; Jorgensen, W. L. J Comput Chem 1997, 18, 1955.
14. (a) Allinger, N. L.; Chen, K.; Lii, J.-H. J Comput Chem 1996, 17, 642
15. (b) Nevins, N.; Chen, K.; Allinger, N. L. J Comput Chem 1996, 17, 669
16. (c) Nevins, N.; Lii, J.-H.; Allinger, N. L. J Comput Chem 1996, 17, 695
17. (d) Nevins, N.; Allinger, N. L. J Comput Chem 1996, 17, 730
18. (e) Allinger, N. L.; Chen, K.; Katzenellenbogen, J. A.; Wilson, S. R.; Anstead, G. M. J Comput Chem 1996, 17, 747
19. (f) It is intended to make the MM4 program available shortly. A UNIX version will be available from Tripos, Inc. (1699 South Hanley Road, St. Louis, MO 63144), and a Windows version will be available from Wavefunction (18401 Von Karmen, Suite 210, Irvine, CA 92715).
20. (a) Article I in this group, Allinger, N. L.; Chen, K.-H.; Lii, J.-H.; Durkin, K. A. J Comput Chem 2003, 24, 1447
21. (b) Article II in this group, Lii, J.-H.; Chen, K.-H.; Durkin, K. A. J Comput Chem 2003, 34, 1473
22. (c) Article III in this group, Lii, J.-H.; Chen, K.-H.; Grindley, B.; Allinger, N. L. J Comput Chem 2003, 24, 1490
23. There is no adequate treatment of hydrogen bonding suitable for carbohydrate studies with molecular mechanics in the published literature to our knowledge. Most of what is needed is given below in ref. (a) and (b). To that must be added the directionality of the lone pair, which is detailed in (c). (a) Lii, J.-H.; Allinger, N. L. J Comput Chem 1998, 19, 1001
24. (b) Lii, J.-H. In Hydrogen Bonding: 2, Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Allinger, N. L., Clark, T., Gasteiger, J., Kollman, P. A., Schaefer III, H. F., Schreiner, P. R., Eds.; John Wiley & Sons; Chichester, 1998, p. 127
25. (c) Lii, J.-H.; Allinger, N. L.; Hydrogen Bonding in MM4, to appear.
26. (a) Edward, J. T. Chem and Ind 1955, 1102
27. (b) Leimux, R. U. In Molecular Rearrangements; de Mayo, P., Ed.; Interscience: New York, 1964.
28. Wiberg, K. B.; Murcko, N. A.; Laidig, K. E.; MacDougall, P. J. J Chem Phys 1990, 94, 6956.
29. Runtz, G.; Bader, R. F. W.; Messer, R. R. Can J Chem 1977, 55, 3040.
30. Yoshida, H.; Tanaka, T.; Matsuura, H. Chem Lett 1996, 8, 637.
31. Chen, K.-H.; Walker, G. A.; Allinger, N. L. J Mol Struct (Theochem) 1999, 490, 87.
32. Chen, K.-H. Unpublished work.
33. Reeves, R. E. J Am Chem Soc 1950, 72, 1499.
34. Guler, L. P.; Yu, Y.-Q.; Kenttamaa, H. I.; Walker, G. A. J Phys Chem A 2002, 106, 6754.
35. Houk, K. N.; Eksterowicz, J. E.; Wu, Y.-D.; Fuglesang, K.; Mitchell, D. B. J Am Chem Soc 1993, 115, 4170
36. Allinger, N. L.; Durkin, K. A. J Comput Chem 2000, 21, 1229.
37. Lii, J.-H.; Ma, B.; Allinger, N. L. J Comput Chem 1999, 20, 1593.
38. Juaristi, E.; Cuevas, G. Tetrahedron 1992, 48, 5019.
39. (a) Radom, L.; Latham, W. A.; Hehre, W. J.; Pople, J. A. J Am Chem Soc 1973, 95, 693
40. (b) Allinger, N. L.; Hindman, D.; Honig, H. J Am Chem Soc 1977, 99, 3282.
41. Body is a general term, not necessarily equivalent to atom. Dipole-dipole interactions are considered to be two-body in effect in the current context, but when induced dipoles are included, they become many-body interactions.
42. Studies of the role of torsion-torsion interaction in molecular mechanics calculations are underway.
43. Wolfe, S. Acc Chem Res 1972, 5, 102.