Reevaluation of Bruice's proximity orientation

Tetrahedron Letters

Volumn 50, Issue 4, 2009, Pages 452-456

  Karaman, Rafik ^a  

^a AL QUDS UNIVERSITY   (Palestine)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE;

AB INITIO CALCULATION; ARTICLE; CYCLIZATION; DENSITY FUNCTIONAL THEORY; KINETICS; MOLECULAR MECHANICS; THERMODYNAMICS;

EID: 57349093360     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.11.041     Document Type: Article

References (64)

1. Fersht A. Structure and Mechanism in Protein Science: A Guide to Enzyme Catalysis and Protein Folding (1999), W. H. Freeman and Company, New York
2. Libman J.F., and Greenberg A. Mechanistic Principles of Enzyme Activity (1988), VCH, New York
3. Warshel A., Sharma P.K., Kato M., Xiang Y., Liu H., and Olsson M.H.M. Chem. Rev. 106 (2006) 3210
4. Warshel A., and Levitt M. J. Mol. Biol. 103 (1976) 227
5. Warshel A., Naray-Szabo G., Sussman F., and Hwang J.-K. Biochemistry 28 (1989) 3629
6. Marcus R.A. J. Chem. Phys. 43 (1965) 679
7. Warshel A. Proc. Natl. Acad. Sci. U.S.A. 75 (1978) 5250
8. Ball P. Nature 431 (2004) 396
9. Olsson M.H.M., Parson W.W., and Warshel A. Chem. Rev. 105 (2006) 1737
10. Page M.I., and Jencks W.P. Proc. Natl. Acad. Sci. U.S.A. 68 (1971) 1678
11. Page M.I. Chem. Soc. Rev. 2 (1973) 295
12. Page M.I. Angew. Chem., Int. Ed. Engl. 16 (1977) 449
13. Page M.I., and Jencks W.P. Gazz. Chim. Ital. 117 (1987) 455
14. Bruice T.C., and Lightstone F.L. Acc. Chem. Res. 32 (1999) 127
15. Lightstone F.L., and Bruice T.C. J. Am. Chem. Soc. 119 (1997) 9103
16. Lightstone F.L., and Bruice T.C. J. Am. Chem. Soc. 118 (1996) 2595
17. Lightstone F.L., and Bruice T.C. J. Am. Chem. Soc. 116 (1994) 10789
18. Bruice T.C., and Bradbury W.C. J. Am. Chem. Soc. 90 (1968) 3803
19. Bruice T.C., and Bradbury W.C. J. Am. Chem. Soc. 87 (1965) 4846
20. Bruice T.C., and Pandit U.K. J. Am. Chem. Soc. 82 (1960) 5858
21. Bruice T.C., and Pandit U.K. Proc. Natl. Acad. Sci. U.S.A. 46 (1960) 402
22. Menger F.M. Acc. Chem. Res. 18 (1985) 128
23. Menger F.M., Chow J.F., Kaiserman H., and Vasquez P.C. J. Am. Chem. Soc. 105 (1983) 4996
24. Menger F.M. Tetrahedron 39 (1983) 1013
25. Menger F.M., Grossman J., and Liotta D.C. J. Org. Chem. 48 (1983) 905
26. Menger F.M., Galloway A.L., and Musaev D.G. Chem. Commun. (2003) 2370
27. Menger F.M. Pure Appl. Chem. 77 (2005) 1873 and references cited therein
28. Dafforn A., and Koshland Jr. D.E. Proc. Natl. Acad. Sci. U.S.A. 68 (1971) 2463
29. Dafforn A., and Koshland Jr. D.E. Bioorg. Chem. 1 (1971) 129
30. Dafforn A., and Koshland Jr. D.E. Biochem. Biophys. Res. Commun. 52 (1973) 779
31. Storm D.R., and Koshland Jr. D.E. Proc. Natl. Acad. Sci. U.S.A. 66 (1970) 445
32. Storm D.R., and Koshland Jr. D.E. J. Am. Chem. Soc. 94 (1972) 5805
33. Storm D.R., and Koshland Jr. D.E. J. Am. Chem. Soc. 94 (1972) 5815
34. Milstein S., and Cohen L.A. J. Am. Chem. Soc. 92 (1970) 4377
35. Milstein S., and Cohen L.A. Proc. Natl. Acad. Sci. U.S.A. 67 (1970) 1143
36. Milstein S., and Cohen L.A. J. Am. Chem. Soc. 94 (1972) 9158
37. Borchardt R.T., and Cohen L.A. J. Am. Chem. Soc. 94 (1972) 9166
38. Borchardt R.T., and Cohen L.A. J. Am. Chem. Soc. 94 (1972) 9175
39. Borchardt R.T., and Cohen L.A. J. Am. Chem. Soc. 95 (1973) 8308
40. Borchardt R.T., and Cohen L.A. J. Am. Chem. Soc. 95 (1973) 8313
41. King M.M., and Cohen L.A. J. Am. Chem. Soc. 105 (1983) 2752
42. Hillery P.S., and Cohen L.A. J. Org. Chem. 48 (1983) 3465
43. Karaman, R. In Presented in Part at the 1st International Conference on Drug Design and Discovery in Dubai, UAE, February 4-7, 2008.
44. Karaman R. Tetrahedron Lett. 49 (2008) 5998
45. Karaman, R. Bioorg. Chem. 2008. doi 10.1016/j.bioorg.2008.08.006.
46. Karaman, R. J. Phys. Org. Chem., submitted for publication.
47. http://www.gaussian.com.
48. Burker U., and Allinger N.L. Molecular Mechanics (1982), American Chemical Society, Washington, DC
49. Rappé A.K., Casewit C.J., Colwell K.S., Goddard W.A., and Skiff W.M. J. Am. Chem. Soc. 114 (1992) 10024
50. Casewit C.J., Colwell K.S., and Rappé A.K. J. Am. Chem. Soc. 114 (1992) 10035
51. Casewit C.J., Colwell K.S., and Rappé A.K. J. Am. Chem. Soc. 114 (1992) 10046
52. Rappé A.K., and Goddard W.A. J. Phys. Chem. 95 (1991) 3358
53. Rappé A.K., Colwell K.S., and Casewit C.J. Inorg. Chem. 32 (1993) 3438
54. Dewar M.J.S., Zoebisch E.G., Healy E.F., and Stewart J.J.P. J. Am. Chem. Soc. 107 (1985) 3902
55. Dewar M.J.S., Ford G.P., McKee M.L., Rzepa H.S., Thoel W., and Yamaguchi Y. J. Mol. Struct. 43 (1978) 135
56. Murrell J.N., and Laidler K.J. Trans. Faraday Soc. 64 (1968) 371
57. http://www.cmbi.kun.nl/~schaft/molden/molden.html.
58. Goldblum A., and Loew G.H. J. Am. Chem. Soc 107 (1985) 4265
59. Muller K. Angew. Chem., Int. Ed. Engl. 19 (1980) 1
60. Dewar M.J.S., and Kirschner S. J. Am. Chem. Soc. 93 (1971) 4290
61. Dorigo A.E., and Houk K.N. J. Am. Chem. Soc. 109 (1987) 3698
62. Houk K.N., Tucker J.A., and Dorigo A.E. Acc. Chem. Res. 23 (1990) 107
63. Newman M.S. Steric Effects in Organic Chemistry (1956), Wiley, New York
64. Streitweiser Jr. A., and Heathcock C.H. Introduction to Organic Chemistry. 3rd ed. (1985), MacMillan, New York