Intramolecular N-H⋯S hydrogen bonding in the zinc thiolate complex [TmPh]ZnSCH2C(O)NHPh: A mechanistic investigation of thiolate alkylation as probed by kinetics studies and by kinetic isotope effects

Journal of the American Chemical Society

Volumn 127, Issue 40, 2005, Pages 14039-14050

  Morlok, Melissa M ^a   Janak, Kevin E ^a   Zhu, Guang ^a   Quarless, Duncan A ^a   Parkin, Gerard ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; COMPLEXATION; DNA; HYDROGEN BONDS; LITHIUM COMPOUNDS; MOLECULAR STRUCTURE; PROBABILITY DENSITY FUNCTION; PROTEINS; X RAY DIFFRACTION;

DENSITY FUNCTIONAL THEORY (DFT); DISSOCIATIVE MECHANISMS; DNA REPAIR PROTEINS; ZINC THIOLATE COMPOUNDS;

ZINC COMPOUNDS;

HYDROGEN; ISOTOPE; LIGAND; NITROGEN; PROTEIN; SULFUR; THIOLACID; TRIS(2 MERCAPTO 1 PHENYLIMIDAZOLYL)HYDROBORATO LIGAND; UNCLASSIFIED DRUG; ZINC;

ALKYLATION; ARTICLE; CALCULATION; CHEMICAL REACTION KINETICS; DENSITY FUNCTIONAL THEORY; DNA REPAIR; HYDROGEN BOND; KINETICS; X RAY DIFFRACTION;

ALKYLATION; CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; KINETICS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; SULFHYDRYL COMPOUNDS; TEMPERATURE; ZINC;

EID: 26444526880     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0536670     Document Type: Article

References (168)

1. (a) Vallee, B. L.; Auld, D. S. Acc. Chem. Res. 1993, 26, 543-551.
2. (b) Auld, D. S. Struct. Bonding (Berlin) 1997, 89, 29-50.
3. (c) Coleman, J. E. Curr. Opin. Chem. Biol. 1998, 2, 222-234.
4. (d) Rahuel-Clermont, S.; Dunn, M. F. Copper Zinc Inflammatory Degener. Dis. 1998, 47-59.
5. (e) Holm, R. H.; Kennepohl, P.; Solomon, E. I. Chem. Rev. 1996, 96, 2239-2314.
6. (f) Lipscomb, W. N.; Sträter, N. Chem. Rev. 1996, 96, 2375-2433.
7. (g) Lindskog, S. Pharmacol. Ther. 1997, 74, 1-20.
8. (a) Parkin, G. Chem. Rev. 2004, 104, 699-767.
9. (b) Parkin, G. Chem. Commun. 2000, 1971-1985.
10. (c) Parkin, G. Metal Ions in Biological Systems; Sigel, A., Sigel, H., Eds.; Marcel Dekker: New York, 2001; Vol. 38, Ch. 14, pp 411-460.
11. (a) Myers, L. C.; Terranova, M. P.; Ferentz, A. E.; Wagner, G.; Verdine, G. L. Science 1993, 261, 1164-1167.
12. (b) Myers, L. C.; Jackow, F.; Verdine, G. L. J. Biol. Chem. 1995, 270, 6664-6670.
13. Other zinc proteins that involve zinc-thiolate alkylation in their mechanisms of action include methionine synthase, methanol-coenzyme M methyltransferase, farnesyl-protein transferase, and geranylgeranyl-protein transferase. See (a) Matthews, R. G.; Goulding, C. W. Curr. Opin. Chem. Biol. 1997, 1, 332-339.
14. (b) Hightower, K. E.; Fierke, C. A. Curr. Opin. Chem. Biol. 1999, 3, 176-181.
15. (c) Strickland, C. L.; Weber, P. C. Curr. Opin. Drug Discovery Dev. 1999, 2, 475-483.
16. (d) Penner-Hahn, J. E. Zn catalyzed alkyl-transfer reactions: A new class of biological Zn sites. Indian J. Chem., Sect. A 2002, 41, 13-21.
17. (e) Matthews, R. G. Acc. Chem. Res. 2001, 34, 681-689.
18. (f) Harris, C. M.; Poulter, C. D. Nat. Prod. Rep. 2000, 17, 137-144.
19. (g) McCall, K. A.; Huang, C.-C.; Fierke, C. A. J. Nutr. 2000, 130, 1437S-1446S.
20. In addition to alkylation, proteolytic cleavage of zinc-thiolate groups is also of relevance, as illustrated by the matrix metalloproteinases (matrixins), a class of enzymes that are essential for embryonic development, wound healing, bone and growth development, and other physiological remodeling processes. See, for example, (a) Borkakoti, N. Curr. Opin. Drug Discovery Dev. 1999, 2, 449-462.
21. (b) Bode, W.; Fernandez-Catalan, C.; Tschesche, H.; Grams, F.; Nagase, H.; Maskos, K. Cell. Mol. Life Sci. 1999, 55, 639-652.
22. (c) Nagase, H.; Woessner, J. F., Jr. J. Biol. Chem. 1999, 274, 21491-21494.
23. (d) Stöcker, W.; Grams, F.; Baumann, U.; Reinemer, P.; Gomis-Rüth, F.-X.; McKay, D. B.; Bode, W. Protein Sci. 1995, 4, 823-40.
24. (a) Maret, W. Biochemistry 2004, 43, 3301-3309.
25. (b) Iuchi, S. Cell. Mol. Life Sci. 2001, 58, 625-635.
26. (c) Berg, J. M.; Shi, Y. Science 1996, 271, 1081-1085.
27. (d) Laity, J. H.; Lee, B. M.; Wright, P. E. Curr. Opin. Struct. Biol. 2001, 11, 39-46.
28. (e) Berg, J. M.; Godwin, H. A. Annu. Rev. Biophys. Biomol. Struct. 1997, 26, 357-371.
29. Maynard, A. T.; Covell, D. G. J. Am. Chem. Soc. 2001, 123, 1047-1058.
30. (a) Platts, J. A.; Howard, S. T.; Bracke, B. R. F. J. Am. Chem. Soc. 1996, 118, 2726-2733.
31. (b) Sennikov, P. G. J. Phys. Chem. 1994, 98, 4973-4981.
32. See, for example, (a) Okamura, T.-A.; Takamizawa, S.; Ueyama, N.; Nakamura, A. Inorg. Chem. 1998, 37, 18-28.
33. (b) François, S.; Rohmer, M. M.; Bénard, M.; Moreland, A. C.; Rauchfuss, T. B. J. Am. Chem. Soc. 2000, 122, 12743-12750.
34. (c) McGuire, D. G.; Khan, M. A.; Ashby, M. T. Inorg. Chem. 2002, 41, 2202-2208 and references therein.
35. (d) Conry, R. R.; Tipton, A. A. J. Biol. Inorg. Chem. 2001, 6, 359-366.
36. (e) Huang, J.; Dewan, J. C.; Walters, M. A. Inorg. Chim. Acta 1995, 228, 199-206.
37. (f) Ueyama, N.; Taniuchi, K.; Okamura, T.; Nakamura, A.; Maeda, H.; Emura, S. Inorg. Chem. 1996, 35, 1945-1951.
38. (g) Ueyama, N.; Okamura, T. A.; Nakamura, A. J. Am. Chem. Soc. 1992, 114, 8129-8137.
39. (a) Karlin, S.; Zhu, Z.-Y. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 14231-14236.
40. (b) Simonson, T.; Calimet, N. Proteins 2002, 49, 37-48.
41. (c) Dudev, T.; Lim, C. J. Am. Chem. Soc. 2002, 124, 6759-6766.
42. Myers, L. C.; Verdine, G. L.; Wagner, G. Biochemistry 1993, 32, 2, 14089-14094.
43. Bridgewater, B. M.; Fillebeen, T.; Friesner, R. A.; Parkin, G. J. Chem. Soc., Dalton Trans. 2000, 4494-4496.
44. (a) Kimblin, C.; Bridgewater, B. M.; Churchill, D. G.; Parkin, G. Chem. Commun. 1999, 2301-2302.
45. (b) Bridgewater, B. M.; Parkin, G. J. Am. Chem. Soc. 2000, 122, 7140-7141.
46. (c) Bridgewater, B. M.; Parkin, G. Inorg. Chem. Commun. 2001, 4, 126-129.
47. (a) Docrat, A.; Morlok, M. M.; Bridgewater, B. M.; Churchill, D. G.; Parkin, G. Polyhedron 2004, 23, 481-488.
48. (b) Morlok, M. M.; Docrat, A.; Janak, K. E.; Tanski, J. M.; Parkin, G. Dalton Trans. 2004, 3448-3452.
49. R]ZnX complexes, see (a) Melnick, J. G.; Docrat, A.; Parkin, G. Chem. Commun. 2004, 2870-2871.
50. (b) Ibrahim, M. M.; Shu, M.; Vahrenkamp, H. Eur. J. Inorg. Chem. 2005, 1388-1397 and references therein.
51. (a) Swenson, D.; Baenziger, N. C.; Coucouvanis, D. J. Am. Chem. Soc. 1978, 100, 1932-1934.
52. (b) Ueyama, N.; Sugawara, T.; Sasaki, K.; Nakamura, A.; Yamashita, S.; Wakatsnki, Y.; Yamazaki, H.; Yasuoka, N. Inorg. Chem. 1988, 27, 741-747.
53. (c) Coucouvanis, D.; Swenson, D.; Baenziger, N. C.; Murphy, C.; Holah, D. G.; Sfarnas, N.; Simopoulos, A.; Kostikas, A. J. Am. Chem. Soc. 1981, 103, 3350-3362.
54. (a) Silver, A.; Koch, S. A.; Millar, M. Inorg. Chim. Acta 1993, 205, 9-14.
55. (b) Maelia, L. E.; Millar, M.; Koch, S. A. Inorg. Chem. 1992, 31, 4594-4600.
56. (c) Koch, S. A.; Maelia, L. E.; Millar, M. J. Am. Chem. Soc. 1983, 105, 5944-5945.
57. Otto, J.; Jolk, I.; Viland, T.; Wonnemann, R.; Krebs, B. Inorg. Chim. Acta 1999, 285, 262-268.
58. Chiou, S.-J.; Innocent, J.; Riordan, C. G.; Lam, K.-C.; Liable-Sands, L.; Rheingold, A. L. Inorg. Chem. 2000, 39, 4347-4353.
59. i (a) Kimblin, C.; Bridgewater, B. M.; Hascall, T.; Parkin, G. J. Chem. Soc., Dalton Trans. 2000, 891-897.
60. (b) Alvarez, H. M.; Tran, T. B.; Richter, M. A.; Alyounes, D. M.; Rabinovich, D.; Tanski, J. M.; Krawiec, M. Inorg. Chem. 2003, 42, 2149-2156.
61. (c) Tesmer, M.; Shu, M.; Vahrenkamp, H. Inorg. Chem. 2001, 40, 4022-4029.
62. (d) Kimblin, C.; Bridgewater, B. M.; Churchill, D. G.; Hascall, T.; Parkin, G. Inorg. Chem. 2000, 39, 4240-4243.
63. (e) Shu, M. H.; Walz, R.; Wu, B.; Seebacher, J.; Vahrenkamp, H. Eur. J. Inorg. Chem. 2003, 2502-2511.
64. (f) Lanfranchi, M.; Marchiò, L.; Mora, C.; Pellinghelli, M. A. Inorg. Chim. Acta 2004, 357, 367-375.
65. (g) Nowell, I. W.; Cox, A. G.; Raper, E. S. Acta Crystallogr., Sect. B 1979, 35, 3047-3050.
66. (h) Wilk, A.; Hitchman, M. A.; Massa, W.; Reinen, D. Inorg. Chem. 1993, 32, 2483-2490.
67. (i) Armstrong, K. E.; Crane, J. D.; Whittingham, M. Inorg. Chem. Commun. 2004, 7, 784-787.
68. Indeed, Vahrenkamp has recently commented on the paucity of structurally characterized zinc-amino acid and zinc-peptide complexes. See Rombach, M.; Gelinsky, M.; Vahrenkamp, H. Inorg. Chim. Acta 2002, 334, 25-33.
69. For some tris(pyrazolyl)hydroborato zinc complexes that incorporate protected cysteine and homocysteine derivatives, see (a) Ruf, M.; Burth, R.; Weis, K.; Vahrenkamp, H. Chem. Ber. 1996, 129, 1251-1257.
70. (b) Brand, U.; Rombach, M.; Seebacher, J.; Vahrenkamp, H. Inorg. Chem. 2001, 40, 6151-6157.
71. b (a) Bell, P.; Sheldrick, W. S. Z. Naturforsch. B 1984, 39, 1732-1737.
72. (b) Shindo, H.; Brown, T. L. J. Am. Chem. Soc. 1965, 87, 1904-1909.
73. Bhandari, C. S.; Sogani, N. C.; Mahnot, U. S. J. Prakt. Chem./Chem.-Ztg. 1971, 313, 849-854.
74. For a discussion of the distinction between normal and dative covalent bonds, see Haaland, A. Angew. Chem., Int. Ed. Engl. 1989, 28, 992-1000.
75. c (a) Bateja, S.; Chandrashekhar, S.; Bhandari, C. S.; Sogani, N. C. J. Chin. Chem. Soc. 1979, 26, 173-176.
76. (b) Bhandra, C. S.; Mehnot, U. S.; Sogani, N. C. Bull. Acad. Pol. Sci., Ser. Sci. Chem. 1972, 20, 91-100.
77. (c) See Supporting Information.
78. - derivatives. See Huang, J.; Ostrander, R. L.; Rheingold, A. L.; Leung, Y.; Walters, M. A. J. Am. Chem. Soc. 1994, 116, 6769-6776.
79. (a) Allen, F. H.; Bird, C. M.; Rowland, R. S.; Raithby, P. R. Acta Crystallogr. 1997, B53, 696-701.
80. (b) Allen, F. H.; Bird, C. M.; Rowland, R. S.; Raithby, P. R. Acta Crystallogr. 1997, B53, 680-695.
81. 2C(O)N(H)Ph is significantly shorter than a hydrogen bonding interaction involving a sulfide ligand [3.377(3) Å]. See Larsen, P. L.; Gupta, R.; Powell, D. R.; Borovik, A. S. J. Am. Chem. Soc. 2004, 126, 6522-6523.
82. (a) Shi, X.-F.; Sun, W.-Y.; Zhang, L.; Li, C.-D. Spectrosc. Acta, Part A 2000, 56, 603-613.
83. (b) Sun, W.-Y.; Zhang, L.; Yu, K.-B. J. Chem. Soc., Dalton Trans. 1999, 795-798.
84. (a) Smith, J. N.; Shirin, Z.; Carrano, C. J. J. Am. Chem. Soc. 2003, 125, 868-869.
85. (b) Smith, J. N.; Hoffman, J. T.; Shirin, Z.; Carrano, C. J. Inorg. Chem. 2005, 44, 2012-2017.
86. Chiou, S.-J.; Riordan, C. G.; Rheingold, A. L. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 3695-3700.
87. 32).
88. On the other hand, C-H⋯S interactions in Zn complexes have been shown to be sufficiently weak that they do not exhibit any structure-directing properties. See Bond, A. D.; Jones, W. J. Chem. Soc., Dalton Trans. 2001, 3045-3051.
89. (a) Myers, L. C.; Wagner, G.; Verdine, G. L. J. Am. Chem. Soc. 1995, 117, 10749-10750.
90. (b) He, C.; Wei, H.; Verdine, G. L. J. Am. Chem. Soc. 2003, 125, 1450-1451.
91. Hellström, N.; Lauritzson, T Chem. Ber. 1936, 69, 1999-2002.
92. Ph]Znl and PhSMe. See ref 12.
93. (a) Wilker, J. J.; Lippard, S. J. J. Am. Chem. Soc. 1995, 117, 8682-8683.
94. (b) Wilker, J. J.; Lippard, S. J. Inorg. Chem. 1997, 36, 969-978.
95. (a) Brand, U.; Rombach, M.; Vahrenkamp, H. Chem. Commun. 1998, 2717-2718.
96. (b) Burth, R.; Vahrenkamp, H. Z. Anorg. Allg. Chem. 1998, 624, 381-385.
97. (c) Rombach, M.; Vahrenkamp, H. Inorg. Chem. 2001, 40, 6144-6150
98. (d) Ref 22b.
99. (a) Hammes, B. S.; Carrano, C. J. Chem. Commun. 2000, 1635-1636.
100. (b) Hammes, B. S.; Carrano, C. J. Inorg. Chem. 2001, 40, 919-927.
101. Ji, M.; Benkmil, B.; Vahrenkamp, H. Inorg. Chem. 2005, 44, 3518-3523.
102. Hammes, B. S.; Carrano, C. J. Inorg. Chem. 1999, 38, 4593-4600.
103. Warthen, C. R.; Hammes, B. S.; Carrano, C. J.; Crans, D. C. J. Biol. Inorg. Chem. 2001, 6, 82-90.
104. (a) Seebacher, J.; Ji, M.; Vahrenkamp, H. Eur. J. Inorg. Chem. 2004, 409-417.
105. (b) Ji, M.; Vahrenkamp, H. Eur. J. Inorg. Chem. 2005, 1398-1405.
106. Fox, D. C.; Fiedler, A. T.; Halfen, H. L.; Brunold, T. C.; Halfen, J. A. J. Am. Chem. Soc. 2004, 126, 7627-7638.
107. Additional studies involving methylation of a chelated thiolate ligand with MeI suggest that the issue of whether alkylation occurs at a zinc-bound thiolate or a dissociated thiolate is still a matter of debate. See Grapperhaus, C. A.; Tuntulani, T.; Reibenspies, J. H.; Darensbourg, M. Y. Inorg. Chem. 1998, 37, 4052-4058.
108. Huang, C. C.; Hightower, K. E.; Fierke, C. A. Biochemistry 2000, 39, 2593-2602.
109. Atwood, J. A. Inorganic and Organometallic Reaction Mechanisms, 2nd ed.; VCH: New York, 1997.
110. -1 (Carrano, C. J., personal communication).
111. For a compilation of ΔS° values, see Minas da Piedade, M. E.; Martinho Simões, J. A. J. Organomet. Chem. 1996, 518, 167-180.
112. (a) Bullock, R. M.; Bender, B. R. Isotope Methods in Homogeneous Catalysis. In Encyclopedia of Catalysis; Horváth, I. T., Ed.; 2002.
113. (b) Jones, W. D. Acc. Chem. Res. 2003, 36, 140-146.
114. (c) Matsson, O.; Westaway, K. C. Adv. Phys. Org. Chem. 1998, 31, 143-248.
115. (d) Rosenberg, E. Polyhedron 1989, 8, 383-405.
116. (e) Anderson, V. E. Curr. Opin. Struct. Biol. 1992, 2, 757-764.
117. (f) Kohen, A. Prog. React. Kinet. Mech. 2003, 28, 119-156.
118. See, for example (a) Churchill, D. G.; Janak, K. E.; Wittenberg, J. S.; Parkin, G. J. Am. Chem. Soc. 2003, 125, 1403-1420.
119. (b) Janak, K. E.; Churchill, D. G.; Parkin, G. Activation Funct. C-H Bonds, ACS Symp. Ser. 2004, 885, 86-104.
120. See, for example (a) Janak, K. E.; Parkin, G. J. Am. Chem. Soc. 2003, 125, 6889-6891.
121. (b) Janak, K. E.; Parkin, G. Organometallics 2003, 22, 4378-4380.
122. (c) Janak, K. E.; Parkin, G. J. Am. Chem. Soc. 2003, 125, 13219-13224.
123. (d) Janak, K. E.; Shin, J. H.; Parkin, G. J. Am. Chem. Soc. 2004, 126, 13054-13070.
124. Janak, K. E.; Churchill, D. G.; Parkin, G. Chem. Commun. 2003, 22-23.
125. See, for example (a) Slaughter, L. M.; Wolczanski, P. T.; Klinckman, T. R.; Cundari, T. R. J. Am. Chem. Soc. 2000, 122, 7953-7975.
126. (b) Bender, B. R. J. Am. Chem. Soc. 1995, 117, 11239-11246.
127. (c) Abu-Hasanayn, F.; Krogh-Jespersen, K.; Goldman, A. S. J. Am. Chem. Soc. 1993, 115, 8019-8023.
128. (d) Bender, B. R.; Kubas, G. J.; Jones, L. H.; Swanson, B. I.; Eckert, J.; Capps, K. B.; Hoff, C. D. J. Am. Chem. Soc. 1997, 119, 9179-9190.
129. (e) Refs 53 and 54.
130. (a) Wolfsberg, M.; Stern, M. J. Pure Appl. Chem. 1964, 8, 225-242.
131. (b) Melander, L.; Saunders, W. H., Jr. Reaction Rates of Isotopic Molecules; Wiley-Interscience: New York, 1980.
132. (c) Carpenter, B. K. Determination of Organic Reaction Mechanisms; Wiley-Interscience: New York, 1984.
133. (d) Ishida, T. J. Nucl. Sci. Technol. 2002, 39, 407-412.
134. (e) Bigeleisen, J.; Mayer, M. G. J. Chem. Phys. 1947, 15, 261-267.
135. a-c The limiting isotope effect at 0 K is determined by the ZPE term, and small variations in vibrational frequencies are sufficient to cause the neglible isotope effect at ambient temperature to become either strongly normal or inverse at low temperature. (a) Watson, T. M.; Hirst, J. D. J. Phys. Chem. A 2002, 106, 7858-7867.
136. (b) Arjunan, V.; Mohan, S.; Subramanian, S.; Thimme Gowda, B. Spectrochim. Acta A 2004, 60, 1141-1159.
137. (c) Herrebout, W. A.; Clou, K.; Desseyn, H. O. J. Phys. Chem. A 2001, 105, 4865-4881.
138. It is well-known that different vibrations may provide comparable and opposing contributions that minimize the magnitude of secondary isotope effects. See, for example (a) Glad, S. S.; Jensen, F. J. Am. Chem. Soc. 1997, 119, 227-232.
139. (b) Ruggiero, G. D.; Williams, I. H.; Roca, M.; Moliner, V.; Tuñón, I. J. Am. Chem. Soc. 2004, 126, 8634-8635.
140. (c) Moliner, V.; Williams, I. H. J. Am. Chem. Soc. 2000, 122, 10895-10902.
141. (d) Hu, W.-P.; Truhlar, D. G. J. Am. Chem. Soc. 1995, 117, 10726-10734.
142. (e) Barnes, J. A.; Williams, I. H. J. Chem. Soc., Chem. Commun. 1993, 1286-1287.
143. (f) Poirier, R. A.; Wang, Y.; Westaway, K. C. J. Am. Chem. Soc. 1994, 116, 2526-2533.
144. (g) Lee, I. Chem. Soc. Rev. 1995, 223-229.
145. (h) Hasanayn, F.; Streitwieser, A.; Al-Rifai, R. J. Am. Chem. Soc. 2005, 127, 2249-2255.
146. Ref 51c.
147. Saunders, W. H., Jr. Tech. Chem. 1986, 6. Part 1, 565-611.
148. ‡ at the PM3 level using MOPAC: Zn-S (2.53 Å), S-C (2.34 Å), C-1 (2.55 Å), and Zn-1 (2.59 Å). See ref 43.
149. This value for the overall isotope effect assumes that the barrier for the second step is significantly greater than that for the first step (i.e., the condition required to observe second-order kinetics). As the barrier for the second step approaches that for the first step, the overall kinetic isotope effect approaches that for the first step.
150. H > 0.
151. (a) McNally, J. P.; Leong, V. S.; Cooper, N. J. In Experimental Organometallic Chemistry; Wayda, A. L., Darensbourg, M. Y., Eds.; American Chemical Society: Washington, DC, 1987; Ch. 2, pp 6-23.
152. (b) Burger, B. J.; Bercaw, J. E. In Experimental Organometallic Chemistry; Wayda, A. L.; Darensbourg, M. Y., Eds.: American Chemical Society: Washington, DC, 1987; Ch. 4, pp 79-98.
153. (c) Shriver, D. F.; Drezdzon, M. A. The Manipulation of Air-Sensitive Compounds, 2nd ed.; Wiley-Interscience: New York, 1986.
154. C-H = 159 Hz, aryl-CH], 137.27 [s, ipso-C], 167.18 [s, C(O)].
155. Kimblin, C.; Bridgewater, B. M.; Churchill, D. G.; Parkin, G. Chem. Commun. 1999, 2301-2302.
156. 3] 119.71 [s, aryl-CH], 124.64 [s, aryl-CH], 129.07 [s, aryl-CH], 1.37.30 [s, ipso-C], 166.50 [s, C(O)].
157. Sheldrick, G. M. SHELXTL, An Integrated System for Solving, Refining and Displaying Crystal Structures from Diffraction Data; University of Göttingen, Göttingen, Germany, 1981.
158. Jaguar 4.1; Schrödinger Inc.: Portland, OR, 2001.
159. Jaguar 6.0; Schrödinger, Inc.: Portland, OR, 2005.
160. (a) Slater, J. C. Quantum Theory of Molecules and Solids, Vol. 4: The Self-Consistent Field for Molecules and Solids; McGraw-Hill: New York, 1974.
161. (b) Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211.
162. (c) Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
163. (d) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
164. (e) Becke, A. D., J. Chem. Phys. 1993, 98, 5648-5652.
165. (a) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.
166. (b) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284-298.
167. (c) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.
168. Dunning, T. H. J. Chem. Phys. 1989, 90, 1007-1023.