Experimental versus theoretical evidence for the rate-limiting steps in uncatalyzed and H+- and hydrolysis HO-- catalyzed of the amide bond

International Journal of Chemical Kinetics

Volumn 41, Issue 9, 2009, Pages 599-611

  Khan, Niyaz ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINE HYDROLYSIS; AMIDE BOND; AMIDE GROUPS; CARBONYL CARBON; CRITICAL REVIEW; EXPERIMENTAL OBSERVATION; FORMAMIDES; HYDROXIDE IONS; KINETIC APPROACH; LEAVING GROUPS; NUCLEOPHILIC ATTACK; RATE LIMITING; RATE-LIMITING STEPS; THEORETICAL STUDY; WATER REACTION;

HYDROLYSIS; UREA; WATER ANALYSIS;

AMIDES;

EID: 69049089033     PISSN: 05388066     EISSN: 10974601     Source Type: Journal    
DOI: 10.1002/kin.20435     Document Type: Article

References (66)

1. Brown, R. S.;Bennet, A. J.; Slebocka-Tilk, H. Acc Chem Res 1992, 25, 481.
2. Brown, R. S. In The Amide Linkage: Selected Structural Aspects in Chemistry, Biochemistry, and Materials Science; Greenberg, A.; Brenneman, C. A.; Liebman, J. F. (Eds.); Wiley-Interscience: New York, 1999; pp. 85-114.
3. Slebocka-Tilk, H.; Neverov, A. A.; Brown, R. S. J Am Chem Soc 2003, 125, 1851, and references cited therein.
4. Wyness, K. G. J Chem Soc 1958, 2934.
5. Hine, J.; King, R. S.-M.; Midden, R.; Sinha, A. J Org Chem 1981, 46, 3186.
6. Slebocka-Tilk, H.; Sauriol, F.;Monette, M.; Brown, R. S. Can J Chem 2002, 80, 1343.
7. Kahne, D.; Still, W. C. J AmChem Soc 1988, 110, 7529.
8. Radzicka, A.;Wolfenden, R. J AmChem Soc 1996, 118, 6105.
9. Bryant, R. A. R.; Hasen, D. E. J Am Chem Soc 1996, 118, 5498.
10. Bender, M. L. Chem Rev 1960, 60, 53.
11. O'Connor, C. Q. Rev Chem Soc 1970, 24, 553.
12. Deslongchamps, P. In Stereoelectronic Effects in Organic Chemistry; Pergamon: Oxford, UK, 1983; p. 101.
13. Williams, A. J Am Chem Soc 1976, 98, 5645.
14. Slebocka-Tilk, H.; Brown, R. S.; Olekszyk, J. J Am Chem Soc 1987, 109, 4620.
15. Biechler, S. S.; Taft, R. W., Jr. J Am Chem Soc 1957, 79, 4927.
16. Schowen, R. L.; Jayaraman, H.;Kershner, L. JAmChem Soc 1966, 88, 3373.
17. Menger, F. M.; Danohue, J. A. J Am Chem Soc 1973, 95, 432.
18. Young, J. K.; Pazhanisamy, S.; Schowen, R. L. J Org Chem 1984, 49, 4148.
19. Sim, Y.-L.; Ariffin, A.; Khan, M. N. J Org Chem 2008, 73, 3730.
20. Baxter, N. J.; Rigoreau, L. J.M.; Laws, A. P.; Page, M. I. J Am Chem Soc 2000, 122, 3375.
21. Antonczak, S.; Ruiz-Lopez, M. F.; Rivail, J. L. J Am Chem Soc 1994, 116, 3912.
22. Zahn, D. J Phys Chem B 2003, 107, 12303.
23. Mujika, J. I.; Formoso, E.; Mercero, J. M.; Lopez, X. J Phys Chem B 2006, 110, 15000.
24. Pliego, J. R. Chem Phys 2004, 306, 273.
25. Zahn, D. Chem Phys Lett 2004, 383, 134.
26. Xiong, Y.; Zhan, C.-G. J Central China Normal Univ Nat Sci 2004, 38, 344.
27. Xiong, Y.; Zhan, C.-G. J Phys Chem A 2006, 110, 12644.
28. Marlier, J. F.; Dopke, N. C.; Johnstone, K. R.; Wirdzig, T. J. J Am Chem Soc 1999, 121, 4356.
29. Kirsch, J. F. In Isotope Effects on Enzyme Catalyzed Reactions; Cleland, W. W.; O'Leary, M. H.; Northrup, D. B. (Eds.); University Park Press: Baltimore, MD, 1977; p. 100.
30. Gassman, P. G.; Hodgson, P. K. G.; Balchunis, R. J. J Am Chem Soc 1976, 98, 1275.
31. Eigen, M. Angew Chem, Int Ed Engl 1964, 3, 1.
32. Jencks, W. P. Chem Soc Rev 1981, 10, 345
33. Khan, M. N. In Surfactant Science Series; CRC Press, Taylor & Francis Group: Boca Raton, FL, 2006; p. 104.
34. Dantus, M.; Zewail, A. Chem Rev 2004, 104, 1717.
35. Bakowies, D.; Kollman, P. A. J Am Chem Soc 1999, 121, 5712.
36. Elsemongy, M. M.; Abu Elamayem, M. S.; Moussa, M. N. H.; Gouda, M. M. J Indian Chem Soc 1975, LII, 1130.
37. Sim, Y.-L.; Damit, E. F.; Ariffin, A.; Khan, M. N. Int J Chem Kinet 2009, 41, 1.
38. Leichtling, B. H.; Klotz, I. M. Biochemistry 1966, 5, 4026.
39. Perrin, C. L.; Chen, J.-H.; Ohta, B. K. J Am Chem Soc 1999, 121, 2448.
40. Ritchie, C. D.;Wright, D. J.; Huang, D.-S.; Kamego, A. A. J Am Chem Soc 1975, 97, 116.
41. Fisher, J. R.; Barnes, H. L. J Phys Chem 1972, 76, 90.
42. Dobson, J. V.; Thirsk, H. R. Electrochim Acta 1971, 16, 315.
43. Callahan, B. P.; Yuan, Y.; Wolfenden, R. J Am Chem Soc 2005, 127, 10828.
44. Shaw, W. H. R.; Bordeaux, J. J. J Am Chem Soc 1955, 77, 4729.
45. Smith, R. M.; Hansen, D. E. J Am Chem Soc 1998, 120, 8910.
46. Bunton, C. A.; Farber, S. J.;Milbank, A. J. G.;O'Connor, C. J.; Turney, T. A. J Chem Soc, Perkin Trans 2 1972, 1869.
47. Bunton, C. A.; Nayak, B.; O'Connor, C. J. J Org Chem 1968, 33, 572.
48. Sim, Y.-L.; Ariffin, A.; Khan, M. N. Bioorg Chem 2008, 36, 178.
49. Almerindo, G. I.; Pliego, J. R., Jr. J Braz Chem Soc 2007, 18, 696.
50. Kallies, B.; Mitzner, R. J Mol Model 1998, 4, 183.
51. Gorb, L.; Asensio, A.; Tunon, I.; Ruiz-Lopez, M. F. Chem-A Eur J 2005, 11, 6743.
52. Shafer, J. A.; Morawetz, H. J Org Chem 1963, 28, 1899.
53. Fife, T. H.; DeMark, B. R. J Am Chem Soc 1976, 98, 6978.
54. Khan, M. N. J Chem Soc, Perkin Trans 2 1988, 213.
55. Gresser, M. J.; Jencks, W. P. J Am Chem Soc 1977, 99, 6970.
56. Slebocka-Tilk, H.; Rescorla, C. G.; Shirin, S.; Bennet, A. J.; Brown, R. S. J Am Chem Soc 1997, 119, 10969.
57. Barrios, A. M.; Lippard, S. J. J Am Chem Soc 2000, 122, 9172.
58. Barrios, A. M.; Lippard, S. J Inorg Chem 2001, 40, 1250.
59. Estiu, G.; Merz, K. M., Jr. J Phys Chem B 2007, 111, 10263, and references cited therein.
60. Estiu, G.; Merz, K. M., Jr. J Am Chem Soc 2004, 126, 183.
61. Estiu, G.; Merz, K. M., Jr. J Am Chem Soc 2004, 126, 6932.
62. Lynn, K. R. J Phys Chem 1965, 69, 687.
63. Khan, M. N.; Olagbemiro, T. O. J Chem Res (S) 1985, 166.
64. Homer, R. B.; Alwis, K.W. J Chem Soc, Perkin Trans 2 1976, 781.
65. Suarez, D.; Diaz, N.; Merz, K. M., Jr. J Am Chem Soc 2003, 125, 15234.
66. Estiu, G.; Merz, K.M., Jr. Biochemistry 2006, 45, 4429. International Journal