Solvent deuterium kinetic isotope effects for the methanolyses of neutral C=O, P=O and P=S esters catalyzed by a triazacyclododecane : Zn 2+-methoxide complex

Organic and Biomolecular Chemistry

Volumn 3, Issue 24, 2005, Pages 4329-4336

  Maxwell, Chris ^a   Neverov, Alexei A ^a   Brown, R Stan ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COMPLEXATION; DEUTERIUM; FRACTIONATION; ISOTOPES; METHANOL; REACTION KINETICS; SOLVENTS;

DESOLVATION; METHANOLYSES; RESOLVATION; TRIAZACYCLODODECANE;

ESTERS;

EID: 29844455329     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b512378j     Document Type: Article

References (137)

1. (a) T. J. Przystas and T. H. Fife, J. Chem. Soc., Perkin Trans. 2, 1990, 393 and references therein;
2. (b) J. Suh, Acc. Chem. Res., 1992, 25, 273 and references therein;
3. (c) P. Tecilla, U. Tonellato, F. Veronese, F. Fellugg and P. Scrimin, J. Org. Chem., 1997, 62, 7621;
4. (d) J. Chin, V. Jubian and K. Mrejen, J. Chem. Soc., Chem. Commun., 1990, 1326;
5. (e) L. Sayre, K. V. Reddy, A. R. Jacobson and W. Tang, Inorg. Chem., 1992, 31, 935;
6. (f) T. H. Fife, Acc. Chem. Res., 1993, 26, 325;
7. (g) T. H. Fife and R. Bembi, J. Am. Chem. Soc., 1993, 115, 11358;
8. (h) T. N. Parac and N. M. Kostic', J. Am. Chem. Soc., 1996, 118, 51;
9. (i) L. Singh and R. N. Ram, J. Org. Chem., 1994, 59, 710;
10. (j) P. A. Sutton and D. A. Buckingham, Acc. Chem. Res., 1987, 20, 357;
11. (k) E. Kimura, I. Nakamura, T. Koike, M. Shionoya, Y. Kodama, T. Ikeda and M. Shiro, J. Am. Chem. Soc., 1994, 116, 4764;
12. (l) T. N. Parac, G. M. Ullman and N. M. Kostic', J. Am. Chem. Soc., 1999, 121, 3127 and references therein;
13. (m) A. M. Ridder and R. M. Kellogg, in Comprehensive Supramolecular Chemistry Vol. 4: Supramolecular Reactivity and Transport: Bioorganic Systems, ed. Y. Murakami, Elsevier Science Ltd, Oxford, 1996, ch. 11;
14. (n) J. Chin, Acc. Chem. Res., 1991, 24, 145 and references therein.
15. (a) A. Blasko and T. C. Bruice, Acc. Chem. Res., 1999, 32, 475 and references therein;
16. (b) N. H. Williams, B. Takasaki, M. Wall and J. Chin, Acc. Chem. Res., 1999, 32, 485 and references therein;
17. (c) R. A. Moss, B. D. Park, P. Scrimin and G. Ghirlanda, J. Chem. Soc., Chem. Commun., 1995, 1627;
18. (d) R. A. Moss, J. Zhang and K. Bracken, J. Chem. Soc., Chem. Commun., 1997, 1639;
19. (e) J. Sumaoka, S. Miyama and M. Komiyama, J. Chem. Soc., Chem. Commun., 1994, 1755;
20. (f) J. R. Morrow, J. A. Buttrey and K. Berback, Inorg. Chem., 1992, 31, 16;
21. (g) J. R. Morrow, L. A. Buttrey, V. M. Shelton and K. A. Berback, J. Am. Chem. Soc., 1992, 114, 1903;
22. (h) K. P. McCue and J. R. Morrow, Inorg. Chem., 1999, 38, 6136;
23. (i) L. L. Chappell, D. A. Voss, Jr., W. DeW Horrocks, Jr. and J. R. Morrow, Inorg. Chem., 1998, 37, 3989;
24. (j) R. Breslow and B. Zhang, J. Am. Chem. Soc., 1994, 116, 7893;
25. (k) N. Takeda, M. Irisawa and M. Komiyama, J. Chem. Soc., Chem. Commun., 1994, 2773;
26. (l) R. W. Hay and N. Govan, J. Chem. Soc., Chem. Commun., 1990, 714;
27. (m) H.-J. Schneider, J. Rammo and R. Hettich, Angew. Chem., Int. Ed. Engl., 1993, 32, 1716;
28. (n) K. G. Ragunathan and H.-J. Schneider, Angew. Chem., Int. Ed. Engl., 1996, 35, 1219;
29. (o) P. Gómez-Tagle and Y. Yatsimirsky, J. Chem. Soc., Dalton Trans., 1998, 2957;
30. (p) P. Molenveld, J. F. J. Engberson and D. N. Reinhoudt, J. Org. Chem., 1999, 64, 6337 and references therein;
31. (q) S.-I. Kondo, K. Shinbo, T. Yamaguchi, K. Yoshida and Y. Yano, J. Chem. Soc., Perkin Trans. 2, 2001, 128;
32. (r) K. P. McCue and J. R. Morrow, Inorg. Chem., 1999, 38, 6136.
33. (a) W. Lipscomb and N. Sträter, Chem. Rev., 1996, 96, 2375;
34. (b) R. H. Holm, P. Kennepohl and E. I. Solomon, Chem. Rev., 1996, 96, 2239;
35. (c) D. E. Wilcox, Chem. Rev., 1996, 96, 2435;
36. (d) J. E. Coleman, Curr. Opin. Chem. Biol., 1998, 2, 222;
37. (e) D. Gani and J. Wilke, Chem. Soc. Rev., 1995, 24, 55.
38. (a) L. Barr, C. J. Easton, K. Lee, S. F. Lincoln and J. S. Simpson, Tetrahedron Lett., 2002, 7797;
39. (b) T. Koike and E. Kimura, J. Am. Chem. Soc., 1991, 113, 8935;
40. (c) M. M. Ibrahim, K. Ichikawa and M. Shiro, Inorg. Chim. Acta, 2003, 353, 187;
41. (d) T. Itoh, H. Hisada, Y. Usui and Y. Fujii, Inorg. Chim. Acta, 1998, 283, 51;
42. (e) F. M. Menger and T. Tsuno, J. Am. Chem. Soc., 1989, 111, 4903;
43. (f) P. Scrimin, P. Tecilla and U. Tonellato, J. Org. Chem., 1991, 56, 161 and references therein;
44. (g) F. Tafesse, Inorg. Chim. Acta, 1998, 269, 287;
45. (h) P. Scrimmin, G. Ghinlanda, P. Tecilla and R. A. Moss, Langmuir, 1996, 12, 6235;
46. (i) C. A. Bunton, P. Scrimmin and P. Tecilla, J. Chem. Soc., Perkin Trans. 2, 1996, 419;
47. (j) Y. Fujii, T. Itoh and K. Onodera, Chem. Lett., 1995, 305;
48. (k) S. J. Oh, C. W. Yoon and J. W. Park, J. Chem. Soc., Perkin Trans. 2, 1996, 329;
49. (l) T. Berg, A. Simeonov and K. Janda, J. Comb. Chem., 1999, 1, 96;
50. (m) J. R. Morrow and W. C. Trogler, Inorg. Chem., 1989, 28, 2330;
51. (n) R. W. Hay and N. Govan, J. Chem. Soc., Chem. Commun., 1990, 714;
52. (o) D. Kong, A. E. Martell and J. Reibenspies, Inorg. Chim. Acta, 2002, 333, 7;
53. (p) R. W. Hay and N. Govan, Polyhedron, 1998, 17, 463, 2079;
54. (q) R. W. Hay, N. Govan and K. E. Parchment, Inorg. Chem. Commun., 1998, 1, 228;
55. (r) B. L. Tsao, R. J. Pieters and J. Rebek, Jr., J. Am. Chem. Soc., 1995, 117, 2210;
56. (s) M. Yamami, H. Furutachi, T. Yokoyama and H. Ōkawa, Inorg. Chem., 1998, 37, 6832;
57. (t) C. M. Hartshorn, A. Singh and E. L. Chang, J. Mater. Chem., 2002, 12, 602;
58. (u) M. Rombach, C. Maurer, K. Weis, E. Keller and H. Vahrenkamp, Chem.-Eur. J., 1999, 5, 1013;
59. (v) P. R. Norman, A. Tate and P. Rich, Inorg. Chim. Acta, 1988, 145, 211;
60. (w) R. W. Hay, N. Govan and P. R. Norman, Transition Met. Chem. (London), 1998, 23, 133;
61. (x) R. J. Whithey, Can. J. Chem., 1969, 476, 4383;
62. (y) R- S. Brown and M. Zamkanei, Inorg. Chim. Acta, 1985, 201.
63. S. H. Gelman, R. Petter and R. Breslow, J. Am. Chem. Soc., 1986, 108, 2388.
64. J. Suh, S. J. Son and M. P. Suh, Inorg. Chem., 1998, 37, 4872.
65. (a) Advances in Physical Organic Chemistry, ed. V. Gold, Academic Press, New York, 1967;
66. (b) P. R. Norman, A. Tate and P. Rich, Inorg. Chim. Acta, 1988, 145, 211;
67. S. Kuusela,. M. Rantanen and H. Lonnberg, J. Chem. Soc., Perkin Trans. 2, 1995, 2269.
68. (a) K. A. Deal, A. C. Henge and J. N. Burstyn, J. Am. Chem. Soc., 1996, 118, 1713;
69. (b) L. A. Jenkins, J. K. Bashkin, A. D. Pennock, J. Florián and A. Warshel, Inorg. Chem., 1999, 38, 3215;
70. (c) M.-Y. Yang, O. Iranzo, J. P. Richard and J. R. Morrow, J. Am. Chem. Soc., 2005, 127, 1064.
71. (a) S. Sawata, M. Komiyama and K. Yaira, J. Am. Chem. Soc., 1995, 117, 2357;
72. (b) S.-I. Nakano, D. M. Chadalavada and P. C. Bevilacqua, Science, 2000, 287, 1493;
73. (c) Y. Tagaki and K. Taira, J. Am. Chem. Soc., 2002, 124, 3850.
74. T. K. Chang, Y. Chiang, H.-X. Guo, A. J. Kresge, L. Mathew, M. F. Powell and J. A. Wells, J. Am. Chem. Soc., 1996, 118, 8802.
75. (a) A. A. Neverov, T. McDonald, G. Gibson and R. S. Brown, Can. J. Chem., 2001, 79, 1704;
76. (b) A. A. Neverov, N. E. Sunderland and R. S. Brown, Org. Biomol. Chem., 2005, 3, 65.
77. (a) J. S. Tsang, A. A. Neverov and R. S. Brown, J. Am. Chem. Soc., 2003, 125, 7602;
78. (b) T. Liu, A. A. Neverov, J. S. W. Tsang and R. S. Brown, Org. Biomol. Chem., 2005, 3, 1525;
79. (c) J. S. W. Tsang, A. A. Neverov and R. S. Brown, Org. Biomol. Chem., 2004, 2, 3457;
80. (d) W. Desloges, A. A. Neverov and R. S. Brown, Inorg. Chem., 2004, 43, 6752;
81. (e) A. A. Neverov and R. S. Brown, Org. Biomol. Chem., 2004, 2, 2245.
82. R. E. Lewis, A. A. Neverov and R. S. Brown, Org. Biomol. Chem., 2005, 3, 4082.
83. spH is used.
84. spH in methanol is 8.4. E. Bosch, F. Rived, M. Rosés and J. Sales, J. Chem. Soc., Perkin Trans. 2, 1999, 1953.
85. 8b.
86. K. B. Schowen and R. L. Schowen, Methods Enzymol., 1982, 87, 551-607.
87. (a) V. Gold and S. Grist, J. Chem. Soc. (B), 1971, 1665;
88. (b) V. Gold and S. Grist, J. Chem. Soc. (B), 1971, 2282;
89. (c) V. Gold and S. Grist, J. Chem. Soc. (B), 1971, 2285;
90. (d) V. Gold, K. P. Morris and C. F. Wilcox, J. Chem. Soc., Perkin Trans. 2, 1982, 1615.
91. (a) W. P. Huskey and R. L. Schowen, Gazz. Chim. Ital., 1987, 117, 409;
92. (b) C. D. Bryan, K. B. Schowen and R. L. Schowen, Can. J. Chem., 1996, 74, 931.
93. S. A. Melnychuk, A. A. Neverov and R. S. Brown, Angew. Chem., Int. Ed., in press.
94. (a) R. L. Schowen, Isotope Effects on Enzyme Catalyzed Reactions, eds., W. W. Cleland, M. H. O'Leary and D. B. Northrup, University Park Press, Baltimore, 1977;
95. (b) R. L. Schowen, Prog. Phys. Org. Chem., 1972, 9, 275;
96. (c) K. B. J. Schowen, Transition States of Biochemical Processes, ed. R. D. Gandour and R. L. Schowen, Plenem Press, New York, 1978.
97. A. J. Kresge, J. Am. Chem. Soc., 1973, 95, 3065.
98. R. A. More O'Ferrall, Chem. Commun., 1969, 114.
99. A. J. Kresge, R. A. More O'Ferrall and M. F. Powell, Solvent Isotope Effects, Fractionation Factor and Mechanisms of Proton Transfer Reactions, in Isotopes in Organic Chemistry, ed. E. Buneel and C. C. Lee, Elsevier Science Publishers, 1987, vol. 7, p. 256.
100. J. Albery, Solvent Isotope Effects In Proton Transfer Reactions, ed. E. Caldin and V. Gold, Chapman and Hall, London, 1975, pp. 263-316, Table 6.
101. J. W. Kassebaum and D. N. Silverman, J. Am. Chem. Soc., 1989, 111, 2691.
102. 10 reports, it is known that only hydrogens involved in very strong hydrogen bonds have fractionation factors sufficiently different from unity to affect proton inventories. See W. W. Cleland, Biochemistry, 1992, 31, 317;
103. (b) W. W. Cleland and M. Kreevoy, Science, 1994, 264, 1887.
104. A. J. Bennett and R. S. Brown, Physical Organic Chemistry of Acyl Transfer Reactions, in Comprehensive Biological Catalysis: A Mechanistic Reference, vol. l, ed. M. Sinnott, Academic Press, New York, 1997, pp. 293-326, and references therein.
105. J. F. Marlier, J. Am. Chem. Soc., 1993, 115, 5953.
106. J. F. Mata-Segreda, J. Am. Chem. Soc., 2002, 124, 2259.
107. H. Slebocka-Tilk, A. A. Neverov and R. S. Brown, J. Am. Chem. Soc., 2003, 125, 1851.
108. G. R. J. Thatcher and R. Kluger, Adv. Phys. Org. Chem., 1989, 25, 99.
109. C. D. Bryan, K. B. Schowen and R. L. Schowen, Can. J. Chem., 1996, 74, 931.
110. (a) S. Ba-Saif, A. K. Luthra and A. Williams, J. Am. Chem. Soc., 1987, 109, 6362;
111. (b) S. L. Shames and L. D. Byers, J. Am. Chem. Soc., 1981, 103, 6170;
112. (c) A. C. Hengge and R. A. Hess, J. Am. Chem. Soc., 1994, 116, 11256.
113. S. A. Khan and A. J. Kirby, J. Chem. Soc. (B), 1970, 1172.
114. R. Rowell and D. G. Gorenstein, J. Am. Chem. Soc., 1981, 103, 5894.
115. S.-B. Hong and F. M. Rauchel, Biochemistry, 1996, 35, 10904.
116. S. A. Ba-Saif and A. Williams, J. Org. Chem., 1988, 63, 2204.
117. S. A. Ba-Saif, M. A. Waring and A. Williams, J. Am. Chem. Soc., 1990, 112, 8115.
118. S. R. Caldwell, F. M. Raushel, P. M. Weiss and W. W. Cleland, Biochemistry, 1991, 30, 7444.
119. F. M. Menger, J. Am. Chem. Soc., 1966, 88, 5356.
120. obs vs. [catalyst] without any correction for the amount of protium in solution.
121. D = 1.7-1.8, attributable to a 'one proton bridge' with a relatively low fractionation factor of ∼0.57.
122. D = 2 consistent with a general base mechanism.
123. W. P. Jencks, J. Am. Chem. Soc., 1068, 09, 2622.
124. (a) F. M. Menger and M. Ladika, J. Am. Chem. Soc., 1987, 109, 3145;
125. (b) J. Chin, Acc. Chem. Res., 1991, 24, 145.
126. S. L. Johnson, Adv. Phys. Org. Chem., 1969, 91, 2799.
127. (a) K. N. Dalby and W. P. Jencks, J. Am. Chem. Soc., 1997, 119, 7271 and references therein;
128. (b) R. A. McClelland, V. M. Kanagasabapathy, N. S. Banait and S. Steenken, J. Am. Chem. Soc., 1991, 113, 1009;
129. (c) R. S. McClelland, F. L. Cozens, S. Steenken, T. L. Amyes and J. P. Richard, J. Chem. Soc., Perkin Trans. 2, 1993, 1717.
130. 13 indicates the reaction would have to exceed the diffusion limit by 50-fold.
131. (a) D. A. Buckingham, J. MacB. Harrofield and A. M. Sargeson, J. Am. Chem. Soc., 1973, 96, 1726;
132. (b) E. Baraniak, D. A. Buckingham, C. R. Clark, B. H. Moynihan and A. M. Sargeson, Inorg. Chem., 1986, 25, 3466;
133. (c) D. R. Jones, L. F. Lindoy and A. M. Sargeson, J. Am. Chem. Soc., 1983, 105, 7327;
134. (d) J. Chin, M. Banaszczyk, V. Jubian and X. Zhou, J. Am. Chem. Soc., 1989, 111, 186;
135. (e) F. Tafesse, S. S. Massoud and R. M. Milburn, Inorg. Chem., 1985, 24, 2591;
136. (f) A. M. Calafat and L. G. Marzilli, Inorg. Chem., 1992, 31, 1719.
137. The content of the information does not necessarily reflect the position or the policy of the federal government, and no official endorsement should be inferred.