Component analysis of the X-C-Y anomeric effect (X = O, S; Y = F, OMe, NHMe) by DFT molecular orbital calculations and natural bond orbital analysis

Canadian Journal of Chemistry

Volumn 84, Issue 4, 2006, Pages 692-701

  Trapp, Melissa L ^a   Watts, Jonathan K ^b   Weinberg, Noham ^c   Pinto, B Mario ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

^b MCGILL UNIVERSITY   (Canada)

^c UNIVERSITY OF THE FRASER VALLEY   (Canada)

Author keywords

Anomeric effect; Component analysis; Electrostatic; Natural bond orbital analysis; Orbital interaction effects; Steric

Indexed keywords

CHEMICAL BONDS; ELECTROSTATICS; OPTIMIZATION; PROBABILITY DENSITY FUNCTION;

ANOMERIC EFFECTS; COMPONENT ANALYSIS; NATURAL BOND ORBITAL ANALYSIS; ORBITAL INTERACTION EFFECTS; STERICS;

MOLECULAR DYNAMICS;

AMINO ACID DERIVATIVE; CYCLOHEXANE DERIVATIVE; METHYLAMINO; OXACYCLOHEXANE; TETRAHYDROTHIOPYRAN; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL ANALYSIS; CHEMICAL BOND; CONFORMATION; ELECTRICITY; ENERGY; MOLECULE;

EID: 33745926211     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V06-048     Document Type: Article

References (48)

1. J.T. Edward. Chem. Ind. (London), 1102 (1955).
2. R.U. Lemieux and N.J. Chü. Abstr. Papers 133rd Am. Chem. Soc. Meeting, 31N (1958).
3. For leading references: (a) W.A. Szarek and D. Horton (Editors). Anomeric effect: Origin and consequences. ACS Symposium Series 87. American Chemical Society, Washington, D.C. 1979;
4. (b) A.J. Kirby. The anomeric effect and related stereoelectronic effects at oxygen. Springer-Verlag, Berlin. 1983;
5. G.R.J. Thatcher (Editor). The anomeric effect and associated stereoelectronic effects. ACS Symposium Series 539. American Chemical Society, Washington, D.C. 1993;
6. (d) E. Juaristi and G. Cuevas (Editors). The anomeric effect. CRC Press, Boca Raton, Florida. 1995.
7. R.U. Lemieux. Pure Appl. Chem. 25, 527 (1971).
8. E.A.C. Lücken. J. Chem. Soc. 111, 2954 (1959).
9. C. Romers, C. Altona, H.R. Buys, and E. Havinga. Top. Stereochem. 4, 39 (1969).
10. (a) R. Hoffmann, L. Radom, J.A. Pople, P.v.R. Schleyer, W.J. Hehre, and L. Salem. J. Am. Chem. Soc. 94, 6221 (1972);
11. (b) O. Eisenstein, N.T. Anh, Y. Jean, A. Devaquet, J. Cantacuzene, and L. Salem. Tetrahedron, 30, 1717 (1974);
12. (c) S. Wolfe, M.-H. Whangbo, and D.J. Mitchell. Carbohydr. Res. 69, 1 (1979).
13. J.-P. Praly and R.U. Lemieux. Can. J. Chem. 65, 213 (1987).
14. R.U. Lemieux and S. Koto. Tetrahedron, 30, 1933 (1974).
15. (a) B.M. Pinto, H.B. Schlegel, and S. Wolfe. Can. J. Chem. 65, 1658 (1987);
16. (b) S. Wolfe, B. M. Pinto, V. Varma, and R.Y.N. Leung. Can. J. Chem. 68, 1051 (1990).
17. B.M. Pinto and R.Y.N. Leung. In The anomeric effect and associated stereoelectronic effects. ACS Symposium Series 539. Edited by G.R.J. Thatcher. American Chemical Society, Washington, D.C. 1993.
18. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, P. Salvador, J.J. Dannenberg, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, and J.A. Pople. Gaussian 98. Revision A. 11.3 [computer program]. Gaussian, Inc., Pittsburgh, Penn. 2002.
19. (a) C. Lee, W. Yang, and R.G. Parr. Phys. Rev. B 37, 785 (1988);
20. (b) A.D. Becke. Phys. Rev. A, 38, 3098 (1988);
21. (c) A.D. Becke. J. Chem. Phys. 97, 9173 (1992);
22. (d) A.D. Becke. J. Chem. Phys. 98, 5648 (1993);
23. (e) P.J. Stephens, F.J. Devlin, C.F. Chabalowski, and M.J. Frisch. J. Phys. Chem. 98, 11623 (1994).
24. E.D. Glendening, A.E. Reed, J.E. Carpenter, and F. Weinhold. NBO Version 3.1 [computer program]. Theoretical Chemistry Institute, University of Wisconsin, Madison, Wisconsin.
25. (d) J.E. Carpenter and F. Weinhold. THEOCHEM. 46, 41 (1988);
26. (b) J.E. Carpenter. Ph.D thesis, University of Wisconsin, Madison, Wisconsin. 1987;
27. (c) F. Weinhold and J.E. Carpenter. In The structure of small molecules and ions. Edited by R. Naaman and V. Vager. Plenum, New York. 1988. p. 227;
28. (d) A.E. Reed, R.B. Weinstock, and F. Weinhold. J. Chem. Phys. 83, 735 (1985);
29. (e) A.E. Reed and F. Weinhold. J. Chem. Phys. 78, 4066 (1983);
30. (f) J.P. Foster and F. Weinhold. J. Am. Chem. Soc. 102, 7211 (1980);
31. (g) A.E. Reed and F. Weinhold. J. Chem. Phys. 83, 1736 (1985);
32. (h) A.E. Reed, L.A. Curtiss, and F. Weinhold. Chem. Rev. 88, 899 (1988).
33. E.D. Glendening, A.E. Reed, J.E. Carpenter, and F. Weinhold. NBO 3.0 Program Manual, Theoretical Chemistry Institute, University of Wisconsin, Madison, Wisconsin.
34. (a) V.F. Weisskopf. Science (Washington, D.C.), 187, 605 (1975);
35. (b) P.A. Christiansen and W.E. Palke. J. Chem. Phys. 67, 57 (1977).
36. J.K. Badenhoop and F. Weinhold. J. Chem. Phys. 107, 5406 (1997).
37. J.K. Badenhoop and F. Weinhold. Int. J. Quantum Chem. 72, 269 (1999).
38. NBO 5.0 program manual. Edited by F. Weinhold. Theoretical Chemistry Insitute, University of Wisconsin, Madison, Wisconsin. 2001
39. E.D. Glendening, J. Badenhoop, K.A.E. Reed, J.E. Carpenter, J.A. Bohmann, C.M. Morales, and F. Weinhold. GenNBO 5.0 [computer program]. Theoretical Chemistry Institute, University of Wisconsin, Madison, Wisconsin. 2001.
40. M. Wendt and F. Weinhold. NBOView 1.1 [computer program]. Theoretical Chemistry Institute, Madison, Wisconsin. 2001.
41. A.E. Reed and P.v.R. Schleyer. J. Am. Chem. Soc. 109, 7362 (1987).
42. T.A. Albright, J.K. Burdett, and M.-H. Whangbo. Orbital interactions in chemistry. John Wiley and Sons, New York. 1985.
43. S. Wolfe and Z. Shi. Isr. J. Chem. 40, 343 (2000).
44. (a) M.C. Krole, J.M.C. Huige, and C.J. Altona. J. Comput. Chem. 10, 265 (1990);
45. (b) C.J. Cramer. J. Org. Chem. 57, 7034 (1992);
46. (c) R.J. Batchelor, D.F. Green, B.D. Johnston, B.O. Patrick, and B.M. Pinto. Carbohydr. Res. 330, 421 (2001).
47. (a) U. Salzner, and P.v.R. Schleyer. J. Am. Chem. Soc. 115, 10231 (1993);
48. (b) S.D. Kahn, J. Korppi-Tommola, R.Y.N. Leung, and B.M. Pinto. J. Mol. Struct: THEOCHEM, 303, 163 (1994).