Hydrolysis and Condensation Reactions of O- and N-Bound Ligands

  • Robert W. Hay

Abstract

Although scattered references to metal ion promoted reactions are to be found in the early literature it was not until the late 1950’s that the significance of these reactions was fully recognized. A strong Jriving force has been the realization that some 30% of enzymes are metalloenzymes or require metal ions for activity. Many of the reactions dealt with in this chapter have been studied in an attempt to mimic the biochemical systems. Since Kroll’s 1953 observation1 that the hydrolysis of α-amino-acid esters was catalyzed by a number of transition metal ions, a large research effort has been devoted to this area, and the associated field of peptide and amide hydrolysis. In many ways the results obtained have been quite remarkable. Rate enhancements of 109–1011 have been noted in some reactions, values similar to those observed in enzymic reactions. In addition, many advances have occurred in the more general field of inorganic reaction mechanisms.

Keywords

Nickel Catalysis Aldehyde Palladium Cerium 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    H. Kroll, J. Am. Chem. Soc. 74:2036 (1952).Google Scholar
  2. 2.
    Q. Fernando, Advan. Inorg. Chem. Radiochem. 7:185 (1965).Google Scholar
  3. 3.
    R. W. Hay, Pure. Appl. Chem. 13:157 (1963).Google Scholar
  4. 4.
    R. W. Hay, J. Chem. Ed. 43:413 (1965).Google Scholar
  5. 5.
    M. M. Jones, “Ligand Reactivity and Catalysis”, Academic Press, New York (1968).Google Scholar
  6. 6.
    E. Kimura, Yuki Gosei Kagaku. 29:12 (1971).Google Scholar
  7. 7.
    M. M. Jones and W. A. Connor, Ind. Eng. Chem. 55:15 (1963).Google Scholar
  8. 8.
    M. L. Bender in “Reactions of Coordinated Ligands”, Advan. Chem. Ser. 37, American Chemical Society (1963).Google Scholar
  9. 9.
    T. C. Bruice and S. J. Benkovic, “Bio-organic Mechanisms”, Vols. 1 and 2, Benjamin, New York (1966).Google Scholar
  10. 10.
    M. L. Bender, “Mechanisms of Homogeneous Catalysis from Protons to Proteins”, Wiley Interscience, New York (1971).Google Scholar
  11. 11.
    Metal Ions in Biological Systems“, Vol. 5, H. Sigel, ed., Marcel Dekker, New York (1976).Google Scholar
  12. 12.
    R. P. Hanzlik, “Inorganic Aspects of Biological and Organic Chemistry”, Academic Press, New York (1976).Google Scholar
  13. 13.
    R. P. Houghton, “Metal Complexes in Organic Chemistry”, Cambridge University Press, Cambridge (1979).Google Scholar
  14. 14.
    A. E. Martell, Xth International Conference on Coordination Chemistry, Butterworths, London (1968).Google Scholar
  15. 15.
    D.P.N. Satchell, Chem. Soc. Rev. 6:345 (1977).Google Scholar
  16. 16.
    J. P. Candlin, K. A. Taylor and D. T. Thompson, “Reactions of Transition Metal Complexes”, Elsevier, Amsterdam (1968).Google Scholar
  17. 17.
    A. E. Martell in “Metal Ions in Biological Systems”, Vol. 2, H. Sigel, ed., Marcel Dekker, New York, pp. 208–262 (1976).Google Scholar
  18. 18.
    M. M. Taqui Kahn and A. E. Martell, “Homogeneous Catalysis by Metal Complexes”, Academic Press, New York (1974).Google Scholar
  19. 19.
    J. E. Coleman in “Progress in Bio-organic Chemistry”, Vol. 1, E. T. Kaiser and F. J. Kezdy, eds., Wiley-Interscience, New York, 159 (1971).Google Scholar
  20. 20.
    Inorganic Biochemistry“, Vol. 1 and 2, G. L. Eichhorn, ed., Elsevier, London (1973).Google Scholar
  21. 21.
    Inorganic Biochemistry“, Vol. 1, Chemical Society Specialist Periodical Report (1979).Google Scholar
  22. 22.
    R. W. Hay and P. J. Morris, “Metal Ion-Promoted Hydrolysis of Amino Acid Esters and Peptides” in “Metal Ions in Biological Systems”, Vol. 5, H. Sigel, ed., Marcel Dekker, New York (1976).Google Scholar
  23. 23.
    D. A. Buckingham, “Metal-OH and its Ability to Hydrolyze (or Hydrate) Substrates of Biological Interest” in “Biological Aspects of Inorganic Chemistry”, A. W. Addison, W. R. Cullen, D. Dolphin and B. R. James, eds., John Wiley, New York (1976).Google Scholar
  24. 24.
    R. W. Hay and D. R. Williams, “Metal Complexes of Amino-acids Peptides and Proteins” in each odd issue of “Amino-acids Peptides and Proteins”, R. C. Sheppard, ed., Specialist Periodical Report, The Chemical Society, London. From Volume 17 the topic is reviewed annually.Google Scholar
  25. 25.
    For a discussion see D. D. Perrin and B. Dempsey, “Buffers for pH and Metal Ion Control”, Chapman and Hall, London (1974).Google Scholar
  26. 26.
    M. P. Springer and C. Curran, Inorg. Chem. 2:1270 (1963).Google Scholar
  27. 27.
    R. W. Hay and L. J. Porter, Aust. J. Chem. 20:675 (1967).Google Scholar
  28. 28.
    H. Shindo and T. L. Brown, J. Am. Chem. Soc. 87:1904 (1965).Google Scholar
  29. 29.
    Y. K. Sze, A. R. Davies and G. A. Neville, Inorg. Chem. 14:1969 (1975).Google Scholar
  30. 30.
    P. R. Norman and D. A. Phipps, Inorg. Chim. Acta 20:L45 (1976).Google Scholar
  31. 31.
    M. D. Alexander and D. H. Busch, Inorg. Chem. 5:1590 (1966).Google Scholar
  32. 32.
    R. W. Hay, R. Bennett and D. J. Barnes, J.C.S. Dalton Trans. 1524, (1972).Google Scholar
  33. 33.
    K. B. Nolan and A. A. Soudi, J.C.S. Dalton Trans. 1419 (1979).Google Scholar
  34. 34.
    D. A. Buckingham, J. Dekkers and A. M. Sargeson, J. Am. Chem. Soc. 95:4173 (1973).Google Scholar
  35. 35.
    M. L. Bender and B. W. Turnquest, J. Am. Chem. Soc. 79:1889 (1957).Google Scholar
  36. 36.
    R. W. Hay and L. J. Porter, J. Chem. Soc. (B), 1261 (1967).Google Scholar
  37. 37.
    R. W. Hay and P. J. Morris, J. Chem. Soc. (B), 1577 (1970).Google Scholar
  38. 38.
    R. W. Hay and P. J. Morris, J. Chem. Soc. Perkin Trans. II, 1021 (1972).Google Scholar
  39. 39.
    R. W. Hay, L. J. Porter and P. J. Morris, Aust. J. Chem. 19:1197 (1966).Google Scholar
  40. 40.
    J. E. Purdie and N. L. Benoiton, Can. J. Chem. 49:3468 (1971).Google Scholar
  41. 41.
    C. Gustaffson, Ann. Acad. Sci. Fennicae AII, No. 15 (1945).Google Scholar
  42. 42.
    R. P. Bell and B. A. W. Coller, Trans. Faraday Soc. 60:1087 (1964);Google Scholar
  43. R. P. Bell and B. A. W. Coller, Trans. Faraday Soc. 61:1445 (1965).Google Scholar
  44. 43.
    F. H. Westheimer and M. W. Shookoff, J. Am. Chem. Soc. 62:269 (1940).Google Scholar
  45. 44.
    R. P. Bell and M. Robson, Trans. Faraday Soc. 60:893 (1964).Google Scholar
  46. 45.
    J. M. White, R. A. Manning and N. C. Li, J. Am. Chem. Soc. 78:2367 (1956).Google Scholar
  47. 46.
    H. L. Conley and R. B. Martin, J. Phys. Chem. 69:2914 (1965).Google Scholar
  48. 47.
    J. E. Hix and M. M. Jones, Inorg. Chem. 5:1863 (1966).Google Scholar
  49. 48.
    C. Regardh, Acta Pharm. Suec. 3:101 (1966).Google Scholar
  50. 49.
    W. A. Connor, M. M. Jones and D. L. Tuleen, Inorg. Chem. 4:1129 (1965).Google Scholar
  51. 50.
    R. W. Hay and P. K. Banerjee, J. C. S. Dalton Trans. 362 (1981);Google Scholar
  52. R. W. Hay and P. K. Banerjee, Inorg. Chim. Acta. 44:L205 (1980).Google Scholar
  53. 51.
    R. W. Flay and K. B. Nolan, J. C. S. Dalton Trans. 1348 (1975).Google Scholar
  54. 52.
    B. E. Leach and R. J. Angelici, Inorg. Chem. 8:907 (1969).Google Scholar
  55. 53.
    R. J. Angelici and D. Hopgood, J. Am. Chem. Soc. 70:2514 (1968).Google Scholar
  56. 54.
    R. D. Wood, R. Nakon and R. J. Angelici, Inorg. Chem. 17:1088 (1978).Google Scholar
  57. 55.
    J. W. Allison and R. J. Angelici, Inorg. Chem. 10:2338 (1971).Google Scholar
  58. 56.
    R. Nakon, P. R. Rechani and R. J. Angelici, J. Am. Chem. Soc. 96:2117 (1974).Google Scholar
  59. 57.
    R. W. Hay and P. K. Banerjee, unpublished results.Google Scholar
  60. 58.
    R. W. Hay and P. K. Banerjee, J. C. S. Dalton Trans. 2452 (1980).Google Scholar
  61. 59.
    R. W. Flay and P. K. Banerjee, J. C. S. Dalton Trans. 2385 (1980).Google Scholar
  62. 60.
    R. W. Hay and P. K. Banerjee, J. Inorg. Biochem. 14:147 (1981).Google Scholar
  63. 61.
    J. E. Coleman and B. L. Valee, J. Biol. Chem. 236:2244 (1961).Google Scholar
  64. 62.
    S. Lindskog and P. O. Nyman, Biochem. Biophys. Acta. 85:462 (1964).Google Scholar
  65. 63.
    D. E. Newlin, M. A. Pellack and R. Nakon, J. Am. Chem. Soc. 99:1078 (1977).Google Scholar
  66. 64.
    R. W. Hay and P. J. Morris, J. Chem. Soc. (A), 3562 (1971).Google Scholar
  67. 65.
    R. W. Hay and P. J. Morris, J. Chem. Soc. (A), 1518 (1971).Google Scholar
  68. 66.
    N. C. Li, E. Doody and J. M. White, J. Am. Chem. Soc. 79:5859 (1957).Google Scholar
  69. 67.
    H. L. Conley and R. B. Martin, J. Phys. Chem. 69:2923 (1965).Google Scholar
  70. 68.
    L. J. Porter, D. D. Perrin and R. W. Hay, J. Chem. Soc. (A), 118 (1969).Google Scholar
  71. 69.
    J. M. White, R. A. Manning and N. C. Li, J. Am. Chem. Soc. 77:5225 (1955).Google Scholar
  72. 70.
    R. Mathur and N. C. Li, J. Am. Chem. Soc. 86:1289 (1964).Google Scholar
  73. 71.
    R. W. Hay and L. J. Porter, J. Chem. Soc. (A), 127 (1969).Google Scholar
  74. 72.
    T. R. Kelly, Ph.D. thesis, University of Glasgow, (1962).Google Scholar
  75. 73.
    R. W. Hay and P. J. Morris, J. Chem. Soc. (A), 1524 (1971).Google Scholar
  76. 74.
    R. W. Hay and P. J. Morris, J. C. S. Dalton. Trans. 56 (1973); for a preliminary report see idem, Chem. Comm. 732 (1968).Google Scholar
  77. 75.
    R. J. Angelici and B. E. Leach, J. Am. Chem. Soc. 89:4605 (1967).Google Scholar
  78. 76.
    R. J. Angelici and B. E. Leach, J. Am. Chem. Soc. 90:2499 (1968).Google Scholar
  79. 77.
    R. D. Cornelius, Inorg. Chim. Acta 46:L109 (1980).Google Scholar
  80. 78.
    B. E. Leach and R. J. Angelici, J. Am. Chem. Soc. 90:2504 (1968).Google Scholar
  81. 79.
    J. Rodgers and R. A. Jacobson, Inorg. Chim. Acta 13:163 (1975).Google Scholar
  82. 80.
    R. D. Gillard, Inorg. Chim. Acta. Rev. 1:69 (1967).Google Scholar
  83. 81.
    J. E. Hix, Jr. and M. M. Jones, J. Am. Chem. Soc. 90:1723 (1968).Google Scholar
  84. 82.
    R. W. Hay and P. J. Morris, J. Chem. Soc. (A), 1524 (1971).Google Scholar
  85. 83.
    R. W. Hay and P. J. Morris, J. C. S. Chem. Commun. 18 (1969).Google Scholar
  86. 84.
    P. J. Morris and R. B. Martin, J. Inorg. Nucl. Chem. 32:2891 (1970).Google Scholar
  87. 85.
    R. W. Kretsinger, F. A. Cotton and R. F. Bryan, Acta Cryst. 16:651 (1963);Google Scholar
  88. M. M. Harding and S. J. Cole, Acta Cryst. 16:643 (1963);Google Scholar
  89. K. A. Fraser and M. M. Harding, J. Chem. Soc. (A), 415 (1967);Google Scholar
  90. R. Candlin and M. M. Harding, J. Chem. Soc. (A), 421 (1967);Google Scholar
  91. M. M. Harding and H. A. Long, J. Chem. Soc. (A), 2554 (1968).Google Scholar
  92. 86.
    R. J. Sundberg and R. B. Martin, Chem. Rev. 74:471 (1974).Google Scholar
  93. 87.
    D. J. Barnes and L. D. Pettit, J. Inorg. Nucl. Chem. 33:2177 (1971).Google Scholar
  94. 88.
    G. Brookes and L. D. Pettit, J. C. S. Chem. Commun. 813 (1974).Google Scholar
  95. 89.
    J. R. Blackburn and M. M. Jones, J. Inorg. Nucl. Chem. 35:1597 (1973).Google Scholar
  96. 90.
    J. R. Blackburn and M. M. Jones, J. Inorg. Nucl. Chem. 35:1605 (1973).Google Scholar
  97. 91.
    J. E. Baldwin, J. C. S. Chem. Commun. 734 (1976).Google Scholar
  98. 92.
    J. E. Baldwin, J. C. S. Chem. Commun. 233 (1977).Google Scholar
  99. 93.
    P. Woolley, Nature 258:677 (1975).Google Scholar
  100. 94.
    R. H. Prince, D. A. Stotter and P. R. Wolley, Inorg. Chirn. Acta 9:51 (1974).Google Scholar
  101. 95.
    M. R. Caira, L. R. Nassimbeni and P. R. Woolley, Acta Cryst. B31:1334 (1975).Google Scholar
  102. 96.
    E. Breslow in “The Biochemistry of Copper”, J. Peisach, P. Aisen and W. E. Blumberg, eds., Academic Press, New York 149–156 (1966).Google Scholar
  103. 97.
    M. A. Wells, G. A. Rogers and T. C. Bruice, J. Am. Chem. Soc. 98:4336 (1976).Google Scholar
  104. 98.
    E. Chaffee, T. P. Dasgupta and G. M. Harris, J. Am. Chem. Soc. 95:4169 (1973).Google Scholar
  105. 99.
    D. A. Palmer and G. M. Harris, Inorg. Chem. 13:965 (1974).Google Scholar
  106. 100.
    D. A. Buckingham, J. MacB. Harrowfield and A. M. Sargeson, J. Am. Chem. Soc. 95:7281 (1973).Google Scholar
  107. 101.
    J. MacB. Harrowfield, V. Norris and A. M. Sargeson, J. Am. Chem. Soc. 98:7282 (1976).Google Scholar
  108. 102.
    D. A. Buckingham and L. M. Englehardt, J. Am. Chem. Soc. 97:5915 (1975).Google Scholar
  109. 103.
    R. W. Hay, Aust.J.Chem. 17:759 (1964).Google Scholar
  110. 104.
    R. W. Hay and C. R. Clark, Transition Met. Chem. 4:28 (1979).Google Scholar
  111. 105.
    J. A. Bertrand and D. Caine, J. Am. Chem. Soc. 86:2298 (1964).Google Scholar
  112. 106.
    R. P. Houghton and C. S. Williams, Tetrahedron Lett. 5091 (1967).Google Scholar
  113. 107.
    D. S. Sigman and C. T. Jorgenson, J. Am. Chem. Soc. 94:1724 (1972).Google Scholar
  114. 108.
    R. G. Lee, D. A. Long and T. G. Truscott, Trans.Faraday Soc. 65:503 (1969);Google Scholar
  115. D. A. Long and T. G. Truscott, Trans. Faraday Soc. 64:1866 (1968);Google Scholar
  116. D. A. Long and T. G. Truscott, Trans. Faraday Soc. 64:1624 (1968)Google Scholar
  117. D. A. Long and T. G. Truscott, Trans. Faraday Soc. 59:2316 (1963);Google Scholar
  118. D. A. Long and T. G. Truscott, Trans. Faraday Soc. 59:1833 (1963).Google Scholar
  119. 109.
    R. D. Gillard, Inorg. Chim. Acta Rev. 1:69 (1967).Google Scholar
  120. 110.
    H. C. Freeman, Advan. Protein Cherrr. 22:257 (1967).Google Scholar
  121. 111.
    R. D. Gillard, E. D. McKenzie, R. Mason and G. B. Robertson, Coord. Chem. Rev. 1:263 (1966).Google Scholar
  122. 112.
    A. S. Brill, R. B. Martin and R.J.P. Williams in “Electronic Aspects of Biochemistry”, B. Pullman, ed., Academic Press, New York (1964).Google Scholar
  123. 113.
    H. C. Freeman, “The Biochemistry of Copper”, J. Peisach, P. Aisen and W. E. Blumberg, eds., Academic Press, New York pp. 77 ff (1966).Google Scholar
  124. 114.
    C. A. McAuliffe in Inorganic Biochemistry, Vol. 1, Chemical Society Specialist Periodical Report (1979).Google Scholar
  125. 115.
    R. B. Martin, M. Chamberlin and J. T. Edsall, J. Am. Chem. Soc. 82:495 (1960).Google Scholar
  126. 116.
    H. C. Freeman, J. M. Guss and R. L. Sinclair, Chem. Commun. 485 (1960).Google Scholar
  127. 117.
    D. W. Margerum, L. F. Wong, F. P. Bossu, K. L. Chellappa, J. J. Czarnecki, S. T. Kirksey, Jr. and T. A. Neubecker in “Bioinorganic Chemistry II”, K. N. Raymond, ed., Adv. Chem. Ser. 162, A.C.S. Washington (1977).Google Scholar
  128. 118.
    E. W. Wilson and R. B. Martin, Inorg. Chem. 9:528 (1970).Google Scholar
  129. 119.
    H. A. O. Hill and K. A. Raspin, J. Chem. Soc. (A), 619 (1969).Google Scholar
  130. 120.
    E. D. McKenzie, J. Chem. Soc. (A), 1655 (1969).Google Scholar
  131. 121.
    R. D. Gillard, E. D. McKenzie, R. Mason and G. B. Robertson, Nature 209:1347 (1966).Google Scholar
  132. 122.
    M. T. Barnet, H. C. Freeman, D. A. Buckingham, I-Nan Hsu and D. van der Helm, Chem. Commun. 367 (1970).Google Scholar
  133. 123.
    D. L. Rabenstein, Can. J. Chem. 49:3767 (1971).Google Scholar
  134. 124.
    E. Bamann, J. G. Haas and H. Trapmann, Arch. Pharm. 294:569 (1961).Google Scholar
  135. 125.
    E. Bamann and H. Trapmann, Advan. Enzymol. 21:169 (1959).Google Scholar
  136. 126.
    E. Bamann, H. Trapmann and A. Rother, Chem. Ber. 91:1744 (1958);Google Scholar
  137. E. Bamann, H. Trapmann and A. Rother, Naturwissenschaften 43:326 (1956).Google Scholar
  138. 127.
    L. Meriwether and F. H. Westheimer, J. Am. Chem. Soc. 78:5119 (1956).Google Scholar
  139. 128.
    I. J. Grant and R. W. Hay, Aust. J. Chem. 18:1189 (1965).Google Scholar
  140. 129.
    T. Nakata, M. Tasumi and T. Miyazawa, Bull. Chem. Soc. Jpn. 48:1599 (1975).Google Scholar
  141. 130.
    M. Tasumi, S. Takahashi, T. Nakata and T. Miyazawa, Bull. Chem. Soc. Jpn. 48:1595 (1975).Google Scholar
  142. 131.
    L. Lawrence and W. J. Moore, J. Am. Chem. Soc. 73:151 (1951).Google Scholar
  143. 132.
    D. A. Long, T. G. Truscott, J. R. Cronin and R. G. Lee, Trans. Faraday Soc. 67:1094 (1971).Google Scholar
  144. 133.
    J. R. Cronin, D. A. Long and T. G. Truscott, Trans. Faraday Soc. 67:2096 (1971).Google Scholar
  145. 134.
    K. Ohkubo and H. Sakamoto, Bull. Chem. Soc. Jpn. 46:2579 (1973).Google Scholar
  146. 135.
    M. D. Alexander and D. H. Busch, Inorg. Chem. 5:602 (1966).Google Scholar
  147. 136.
    M. D. Alexander and D. H. Busch, Inorg. Chem. 5:1590 (1966).Google Scholar
  148. 137.
    M. D. Alexander and D. H. Busch, J. Am. Chem. Soc. 88:1130 (1966).Google Scholar
  149. 138.
    Y. Wu and D. H. Busch, J. Am. Chem. Soc. 92:3326 (1970).Google Scholar
  150. 139.
    D. A. Buckingham, L. G. Marzilli and A. M. Sargeson, J. Am. Chem. Soc. 89:4539 (1967).Google Scholar
  151. 140.
    D. A. Buckingham, D. M. Foster and A. M. Sargeson, J. Am. Chem. Soc. 90:6032 (1968).Google Scholar
  152. 141.
    See for example M. L. Tobe, Acc. Chem. Res. 3:377 (1970).Google Scholar
  153. 142.
    D. A. Buckingham, D. M. Foster and A. M. Sargeson, J. Am. Chem. Soc. 91:4102 (1969).Google Scholar
  154. 143.
    D. A. Buckingham, D. M. Foster, L. G. Marzilli and A. M. Sargeson, Inorg. Chem. 9:11 (1970).Google Scholar
  155. 144.
    D. A. Buckingham, J. Dekkers, A. M. Sargeson and M. Wein, J. Am. Chem. Soc. 94:4032 (1972).Google Scholar
  156. 145.
    D. A. Buckingham, J. Dekkers and A. M. Sargeson, J. Am. Chem. Soc. 95:4173 (1973).Google Scholar
  157. 146.
    K. Nomiya and H. Kobayashi, Inorg. Chem. 13:409 (1974).Google Scholar
  158. 147.
    D. A. Buckingham and M. Wein, Inorg. Chem. 13:3027 (1974).Google Scholar
  159. 148.
    R. W. Hay and K. B. Nolan, J. C. S. Dalton Trans. 1621 (1975).Google Scholar
  160. 149.
    J. R. Fluckiger, C. W. Schlapfer and C. Couldwell, Inorg. Chem. 19:2493 (1980).Google Scholar
  161. 150.
    H. M. Comley and W. C. E. Higginson, J. C. S. Dalton Trans. 2522 (1972).Google Scholar
  162. 151.
    A. C. Dash, R. K. Nanda and S. K. Mohapatra, J. C. S. Dalton Trans. 897 (1975).Google Scholar
  163. 152.
    R. W. Hay, R. Bennett and D. J. Barnes, J. C. S. Dalton Trans. 1524 (1972).Google Scholar
  164. 153.
    R. W. Hay, R. Bennett and D. P. Piplani, J. C. S. Dalton Trans. 1046 (1973).Google Scholar
  165. 154.
    K. B. Nolan, B. R. Coles and R. W. Hay, J. C. S. Dalton Trans. 2503 (1973).Google Scholar
  166. 155.
    D. A. Buckingham, D. M. Foster and A. M. Sargeson, J. Am. Chem. Soc. 91:3451 (1969).Google Scholar
  167. 156.
    D. A. Buckingham, C. E. Davis and A. M. Sargeson, J. Am. Chem. Soc. 92:6159 (1970).Google Scholar
  168. 157.
    D. A. Buckingham, J. MacB. Harrowfield and A. M. Sargeson, J. Am. Chem. Soc. 96:1726 (1973).Google Scholar
  169. 158.
    D. A. Buckingham, C. E. Davis, D. M. Foster and A. M. Sargeson, J. Am. Chem. Soc. 92:5571 (1970).Google Scholar
  170. 159.
    D. A. Buckingham, J. MacB. Harrowfield and A. M. Sargeson, J. Am. Chem. Soc. 96:1726 (1974).Google Scholar
  171. 160.
    D. A. Buckingham, D. M. Foster and A. M. Sargeson, J. Am. Chem. Soc. 92:6151 (1970).Google Scholar
  172. 161.
    D. A. Buckingham, P. J. Morris, A. M. Sargeson and A. Zanella, Inorg. Chem. 16:1910 (1977).Google Scholar
  173. 162.
    C. J. Boreham, D. A. Buckingham, and F. R. Keene, Inorg. Chem. 18:28 (1979).Google Scholar
  174. 163.
    C. J. Boreham, D. A. Buckingham and F. R. Keene, J. Am. Chem. Soc. 101:1409 (1979).Google Scholar
  175. 164.
    J. P. Collman and D. A. Buckingham, J. Am. Chem. Soc. 85:3039 (1963).Google Scholar
  176. 165.
    D. A. Buckingham and J. P. Collman, Inorg. Chem. 6:1803 (1967).Google Scholar
  177. 166.
    D. A. Buckingham, J. P. Collman, D. A. R. Hopper and L. G. Marzilli, J. Am. Chem. Soc. 89:1082 (1967).Google Scholar
  178. 167.
    L. G. Marzilli and D. A. Buckingham, Inorg. Chem. 7:1042 (1967).Google Scholar
  179. 168.
    E. Kimura, S. Young and J. P. Collman, Inorg. Chem. 9:1183 (1970).Google Scholar
  180. 169.
    M. D. Fenn and J. H. Bradbury, Analyt. Biochem. 49:498 (1972).Google Scholar
  181. 170.
    K. W. Bentley and E. H. Creaser, Inorg. Chem. 13:1115 (1974).Google Scholar
  182. 171.
    K. W. Bentley and E. H. Creaser, Biochem. J. 135:507 (1973).Google Scholar
  183. 172.
    E. Kimura, Inorg. Chem. 13:951 (1974).Google Scholar
  184. 173.
    S. K. Oh and C. B. Storm, Bioinorg. Chem. 3:89 (1973).Google Scholar
  185. 174.
    M-J. Rhee and C. B. Storm, J. Inorg. Biochem. 11:17 (1979).Google Scholar
  186. 175.
    J. P. Collman and P. W. Schneider, Inorg. Chem. 5:1380 (1966).Google Scholar
  187. 176.
    P. W. Schneider and J. P. Collman, Inorg. Chem. 7:2010 (1968).Google Scholar
  188. 177.
    R. D. Gillard and D. A. Phipps, Chem. Commun. 800 (1970).Google Scholar
  189. 178.
    Y. Wu and D. H. Busch, J. Am. Chem. Soc. 94:4115 (1972).Google Scholar
  190. 179.
    A. Y. Girgis and J. I. Legg, J. Am. Chem. Soc. 94:8420 (1972).Google Scholar
  191. 180.
    K. Ohkawa, J. Fujita and Y. Shimura, Bull. Chem. Soc. Jpn. 45:161 (1972).Google Scholar
  192. 181.
    L. F. Vilas-Boas, Ph.D. thesis, University of Kent, UK, (1974).Google Scholar
  193. 182.
    R. W. Hay and D. P. Piplani, Kemiai Közlémenyek. 48:47 (1977); see also ref. 542.Google Scholar
  194. 183.
    W. N. Lipscombe, Accounts Chem. Res. 3:81 (1970).Google Scholar
  195. 184.
    L. G. Marzilli and D. A. Buckingham, Inorg. Chem. 7:1042 (1967).Google Scholar
  196. 185.
    R. J. Dellaca, V. Janson, W. T. Robinson, D. A. Buckingham, L. G. Marzilli, I. E. Maxwell, K. R. Turnbull and A. M. Sargeson, J. C. S. Chem. Commun. 57 (1972)Google Scholar
  197. R. J. Dellaca, V. Janson, W. T. Robinson, D. A. Buckingham, L. G. Marzilli, I. E. Maxwell, K. R. Turnbull and A. M. Sargeson, J. Am. Chem. Soc. 96:1713 (1974).Google Scholar
  198. 186.
    J. P. Collman and E. Kimura, J. Am. Chem. Soc. 89:6096 (1967).Google Scholar
  199. 187.
    R. W. Hay and P. J. Morris, Chem. Commun. 1208 (1969).Google Scholar
  200. 188.
    R. W. Hay, M. L. Jansen and P. L. Cropp, Chem. Commun. 621 (1967).Google Scholar
  201. 189.
    Y. Mitsui, J. Watanabe, Y. Iitaka and E. Kimura, J.C. S. Chem. Commun. 280 (1975).Google Scholar
  202. 190.
    S. C. Chan and F. K. Chan, Aust. J. Chem. 23:1175 (1970).Google Scholar
  203. 191.
    D. A. Buckingham, L. G. Marzilli and A. M. Sargeson, J. Am. Chem. Soc. 89:2772 (1967).Google Scholar
  204. 192.
    D. A. Buckingham, P. A. Marzilli, I. E. Maxwell and A. M. Sargeson, Chem. Commun. 488 (1968).Google Scholar
  205. 193.
    D. A. Phipps, J. Mol. Catal. 5:81 (1979).Google Scholar
  206. 194.
    A. Pasini and L. Casella, J. Inorg. Nucl. Chem. 2133 (1974).Google Scholar
  207. 195.
    A. E. Martell, in “Metal Ions in Biological Systems, ”H. Sigel, ed., Marcel Dekker, New York, Vol. 2, p. 208 (1973);Google Scholar
  208. E. N. Safonova and V. M. Belikov, Russ. Chem. Rev. 43:745 (1974).Google Scholar
  209. 196. (a)
    R. H. Holm in “Inorganic Biochemistry”, G. L. Eichorn, ed., Elsevier, New York, Vol. 2, p. 1137 (1973);Google Scholar
  210. (b).
    D. L. Leussing in “Metal Ions in Biological Systems”, H. Sigel, ed., Marcel Dekker, New York, Vol. 5 p. 2 (1976);Google Scholar
  211. (c).
    J. T. Wrobleski and G. J. Long, Inorg. Chem. 16:2752 (1977).Google Scholar
  212. 197. (a)
    M. Sato, K. Okawa and S. Akabori, Bull. Chem. Soc. Jpn. 30:937 (1957);Google Scholar
  213. (b).
    Y. Ikutani, T. Okuda, M. Sato and S. Akabori, Ibid. 32:203 (1959).Google Scholar
  214. 198.
    S. Akabori, T. T. Otani, R. Marshall, M. Winitz and J. P. Greenstein, Arch. Biochem. Biophys. 83:1 (1959).Google Scholar
  215. 199.
    Y. Ikutani, T. Okuda and S. Akabori, Bull. Chem. Soc. Jpn. 33:582 (1960).Google Scholar
  216. 200.
    R. D. Gillard and P. M. Harrison, J. Chem. Soc. (A), 1957 (1967).Google Scholar
  217. 201.
    J. P. Aune, P. Maldonado, G. Larcheres and M. Pierrot, Chem. Commun. 1351 (1970).Google Scholar
  218. 202.
    J. R. Brush, R. J. Magee, M. J. O’Connor, S. B. Teo, R. J. Geue and M. R. Snow, J. Am. Chem. Soc. 95:2034 (1973).Google Scholar
  219. 203.
    R. D. Gillard, S. H. Laurie, D. C. Price, D. A. Phipps and C. F. Weick, J.C.S. Dalton Trans. 1385 (1974).Google Scholar
  220. 204.
    R. J. Geue, M. R. Snow, J. Springborg, A. J. Herlt, A. M. Sargeson and D. Taylor, J. C. S. Chem. Commun. 285 (1976).Google Scholar
  221. 205.
    M. J. O’Connor, J. F. Smith and S. B. Teo, Aust. J. Chem. 29:375 (1976).Google Scholar
  222. 206.
    K. Noda, M. Bessho, T. Kato and N. Izumiya, Bull. Chem. Soc. Jpn. 43:1834 (1970).Google Scholar
  223. 207.
    M. Fujioka, Y. Nakao and A. Nakahara, J. Inorg. Nucl. Chem. 39:1805 (1977).Google Scholar
  224. 208.
    M. Murakami and K. Takahashi, Bull. Chem. Soc. Jpn. 32:308 (1959).Google Scholar
  225. 209.
    J. C. Dabrowiak and D. W. Cooke, Inorg. Chem. 14:1305 (1975).Google Scholar
  226. 210.
    D. A. Phipps, Inorg. Chim. Acta 27:L103 (1978).Google Scholar
  227. 211.
    K. Harada and J. Oh-hashi, J. Org. Chem. 32:1103 (1967).Google Scholar
  228. 212.
    T. Ichimawa, S. Maeda, Y. Araki and Y. Ishido, J. Am. Chem. Soc. 92:5514 (1970).Google Scholar
  229. 213.
    T. Ichikawa, S. Maeda, T. Okamoto, Y. Araki and Y. Ishido, Bull. Chem. Soc. Jpn. 44:2779 (1971).Google Scholar
  230. 214.
    T. Ichikawa, T. Okamoto, S. Maeda, S. Ohdan, Y. Araki and Y. Ishido, Tetrahedron Lett. 79 (1971).Google Scholar
  231. 215.
    S. Ohdan, T. Akamoto, S. Maeda, T. Ichikawa, Y. Araki and Y. Ishido, Bull. Chem. Soc. Jpn. 46:981 (1973).Google Scholar
  232. 216.
    S. Ohdan, T. Ichikawa, Y. Araki and Y. Ishido, Bull. Chem. Soc. Jpn. 47:1295 (1974).Google Scholar
  233. 217.
    Yu. N. Belokon, V. M. Belikov, S. V. Vitt, M. M. Dolgaya and T. F. Savel’eva, J. C. S. Chem. Commun. 86 (1975).Google Scholar
  234. 218.
    Yu. N. Belokon, V. M. Belikov, S. V. Vitt, T. F. Savel’eva, V. M. Burbelo, V. I. Bakhmutov, C. G. Aleksandrov and Yu. T. Struchkov, Tetrahedron 33:2551 (1977).Google Scholar
  235. 219.
    L. Benoiton, M. Winitz, R. F. Coleman, S. M. Birnbaum and J. P. Greenstein, J. Am. Chem. Soc. 81:1726 (1959).Google Scholar
  236. 220.
    R. D. Gillard and D. A. Phipps, J. C. S. Chem. Commun. 800 (1970).Google Scholar
  237. 221.
    L. G. Stadherr and R. J. Angelici, Inorg. Chem. 14:925 (1975).Google Scholar
  238. 222.
    R. D. Gillard, P. O’Brien, P. R. Norman and D. A. Phipps, J. C. S. Dalton Trans. 1988 (1977).Google Scholar
  239. 223.
    L. Casella, A. Pasini, R. Ugo and M. Visca, J. C. S. Dalton Trans. 1655 (1980).Google Scholar
  240. 224.
    D. A. Buckingham, L. G. Marizilli and A. M. Sargeson, J. Am. Chem. Soc. 89:5433 (1967).Google Scholar
  241. 225.
    J. I. Legg and D. W. Cooke, J. Am. Chem. Soc. 89:6854 (1967).Google Scholar
  242. 226.
    D. H. Williams and D. H. Busch, J. Am. Chem. Soc. 87:4644 (1967).Google Scholar
  243. 227.
    L. E. Erickson, A. J. Dappen and J. C. Uhlenhopp, J. Am. Chem. Soc. 91:2510 (1967).Google Scholar
  244. 228.
    E. S. Gore and M.L.H. Green, J. Chem. Soc. (A), 2315 (1970).Google Scholar
  245. 229.
    P. R. Norman and D. A. Phipps, Inorg. Chim. Acta 24:L35 (1977).Google Scholar
  246. 230.
    W. E. Keyes and J. I. Legg, J. Am. Chem. Soc. 98:4970 (1976).Google Scholar
  247. 231. (a)
    B. T. Golding, G. J. Gainsford, A. J. Herlt and A. M. Sargeson, Angew. Chem. Int. Ed. Engl. 14:495 (1975);Google Scholar
  248. (b).
    B. T. Golding, G. J. Gainsford, A. J. Herlt and A. M. Sargeson, Idem. Tetrahedron 32:389 (1976).Google Scholar
  249. 232.
    I. I. Creaser, J. MacB. Harrowfield, A. J. Herlt, A. M. Sargeson, J. Springborg, R. J. Geue and M. R. Snow, J. Am. Chem. Soc. 99:3181 (1977).Google Scholar
  250. 233.
    A. M. Sargeson, Chem. Brit. 15:23 (1979).Google Scholar
  251. 234.
    D. E. Metzler and E. E. Snell, J. Am. Chem. Soc. 74:769 (1952).Google Scholar
  252. 235.
    D. E. Metzler, J. Olivard and E. E. Snell, J. Am. Chem. Soc. 76:644 (1954).Google Scholar
  253. 236.
    K. Ikawa and E. E. Snell, J. Am. Chem. Soc. 76:4900 (1954).Google Scholar
  254. 237.
    J. Olivard, D. E. Metzler and E. E. Snell, J. Biol. Chem. 199:669 (1952).Google Scholar
  255. 238.
    D. Metzler and E. E. Snell, J. Biol. Chem. 198:353 (1952).Google Scholar
  256. 239.
    J. B. Longenecker and E. E. Snell, J. Am. Chem. Soc. 79:142 (1957).Google Scholar
  257. 240.
    D. E. Metzler, M. Ikawa and E. E. Snell, J. Am. Chem. Soc. 76:648 (1954).Google Scholar
  258. 241.
    Pyrodoxal Catalysis - Enzymes and Model Systems“, E. E. Snell, A. E. Braunstein, E. S. Severin and Y. M. Torchinsky, eds., Interscience, New York (1968).Google Scholar
  259. 242.
    E. E. Snell, P. M. Fasella, A. Braunstein and A. Rossi-Fanelli, “Chemical and Biological Aspects of Pyridoxal Catalysis”, MacMillan, New York (1963).Google Scholar
  260. 243.
    See ref. 9, Vol. 2.Google Scholar
  261. 244.
    L. F. Lindoy, Quart. Rev. Chem. Soc. 25:379 (1971).Google Scholar
  262. 245.
    H. S. Maslen and T. N. Waters, Coord. Chem. Rev. 17:137 (1975).Google Scholar
  263. 246.
    E. J. Corey and R. L. Dawson, J. Am. Chem. Soc. 84:4899 (1962).Google Scholar
  264. 247.
    C. R. Wasmuth and H. Freiser, Talanta 9:1059 (1962).Google Scholar
  265. 248.
    R. H. Barca and H. Freiser, J. Am. Chem. Soc. 88:3744 (1966).Google Scholar
  266. 249.
    R. W. Hay and C. R. Clark, J.C.S. Dalton Trans. 1993 (1977).Google Scholar
  267. 250.
    R. P. Houghton and R. R. Puttner, Chem. Commun. 1270 (1970).Google Scholar
  268. 251.
    R. W. Hay and C. R. Clark, J.C.S. Dalton Trans. 1866 (1977).Google Scholar
  269. 252.
    K. H. Gerber and R. G. Wilkins, A.C.S. Meeting, Dallas, Texas, Abstract 173 (1973).Google Scholar
  270. 253.
    T. H. Fife and V. L. Squillacote, J. Am. Chem. Soc. 100:4787 (1978).Google Scholar
  271. 254.
    T. H. Fife, T. J. Przystas and V. L. Squillacote, J. Am. Chem. Soc. 101:3017 (1979).Google Scholar
  272. 255.
    For a general discussion of intramolecular catalysis see A. J. Kirby and A. R. Fersht in “Progress in Bioinorganic Chemistry”, E. T. Kaiser and F. J. Kezdy, eds., Wiley (1971).Google Scholar
  273. 256.
    T. H. Fife and V. L. Squillacote, J. Am. Chem. Soc. 99:3762 (1977).Google Scholar
  274. 257.
    J. T. Groves and R. M. Dias, J. Am. Chem. Soc. 101:1033 (1979).Google Scholar
  275. 258.
    R. Nakon and R. J. Angelici, Inorg. Chem. 12:1269 (1973).Google Scholar
  276. 259.
    R. W. Hay and K. B. Nolan, J. C. S. Dalton Trans. 2542 (1974).Google Scholar
  277. 260.
    R. W. Hay, K. B. Nolan and M. Shuaib, Transition Met. Chem. 5:230 (1980).Google Scholar
  278. 261.
    R. Breslow, R. Fairweather and J. Keana, J. Am. Chem. Soc. 89:2135 (1967).Google Scholar
  279. 262.
    R. Breslow, “Bioinorganic Chemistry”, Adv. Chem. Ser. No. 100, R. F. Gould, ed., p. 23;Google Scholar
  280. R. Breslow and M. Schmir, J. Am. Chem. Soc. 93:4960 (1971).Google Scholar
  281. 263.
    K. B. Nolan and R. W. Hay, J. C. S. Dalton Trans. 914 (1974).Google Scholar
  282. 264.
    D. Pinnell, G. B. Wright and R. B. Jordan, J. Am. Chem. Soc. 94:6104 (1972).Google Scholar
  283. 265.
    D. A. Buckingham, F. R. Keene and A. M. Sargeson, J. Am. Chem. Soc. 95:5649 (1973).Google Scholar
  284. 266.
    D. A. Buckingham, B. M. Foxman, A. M. Sargeson and A. Zanella, J. Am. Chem. Soc. 94:1007 (1972).Google Scholar
  285. 267.
    K. Sakai, T. Ito and K. Watanabe, Bull. Chem. Soc. Jpn. 40:1660 (1967).Google Scholar
  286. 268.
    S. Komiya, S. Suzuki and K. Watanabe, Bull. Chem. Soc. Jpn. 44:1440 (1971);Google Scholar
  287. K. Watanabe, S. Komiya and A. Suzuki, Ibid. 46:2792 (1973).Google Scholar
  288. 269.
    P.F.D. Barnard, J. Chem. Soc. (A), 2140 (1969).Google Scholar
  289. 270. (a)
    A. W. Zanella and P. C. Ford, J.C.S. Chem. Commun. 795 (1974);Google Scholar
  290. (b).
    A. W. Zanella and P. C. Ford, Inorg. Chem. 14:42 (1975).Google Scholar
  291. 271.
    C. R. Clark and R. W. Hay, J. C. S. Dalton Trans. 2148 (1974).Google Scholar
  292. 272.
    D. A. Buckingham, A. M. Sargeson and A. Zannella, J. Am. Chem. Soc. 94:8246 (1972).Google Scholar
  293. 273.
    D. A. Buckingham, P. J. Morris, A. M. Sargeson and A. Zanella, Inorg. Chem. 16:1910 (1977).Google Scholar
  294. 274.
    K. V. Thimann and S. Mahadevan, Arch. Biochem. Biophys. 105:133 (1964);Google Scholar
  295. S. Mahadevan and K. V. Thimann, Ibid. 107:62 (1964).Google Scholar
  296. 275.
    R. H. Hook and W. C. Robinson, J. Biol. Chem. 239:4257, 4263 (1964).Google Scholar
  297. 276.
    C. Zervos and E. H. Cordes, J. Am. Chem. Soc. 90:6892 (1968).Google Scholar
  298. 277.
    E. Bamann and H. Trapmann, Advan. Enzymol. 21:169 (1959).Google Scholar
  299. 278.
    T. C. Bruice and S. J. Benkovic, “Bioorganic Mechanisms”, Vol.2, W. A. Benjamin, New York, Chapters 5, 6 and 7 (1966).Google Scholar
  300. 279.
    J. R. Cox and O. B. Ramsay, Chem. Rev. 64:317 (1964).Google Scholar
  301. 280.
    C. A. Bunton, J. Chem. Ed. 45:21 (1968).Google Scholar
  302. 281.
    J. Emsley and D. Hall, “The Chemistry of Phosphorus”, Harper Row, London (1975).Google Scholar
  303. 282.
    F. H. Westheimer, Accounts Chem. Res. 1:70 (1968).Google Scholar
  304. 283.
    P. Gillespie, F. Ramirez, I. Ugi and D. Marquading, Angew. Chem. Int. Ed. Engl. 12:91 (1973).Google Scholar
  305. 284.
    R. F. Hudson, “Structure and Mechanism in Organophosphorus Chemistry”, Academic Press, New York (1965).Google Scholar
  306. 285.
    B. J. Walker, “Organophosphorus Chemistry”, Penguin, Harmondsworth, Mdx. (1972).Google Scholar
  307. 286.
    R. D. Cook, C. E. Diebert, W. Schwarz, P. C. Turley and P. Haake, J. Am. Chem. Soc. 95:8688 (1973).Google Scholar
  308. 287.
    M. Gallagher, A. Munoz, G. Gence and M. Koenig, J. C. S. Chem. Commun. 321 (1976).Google Scholar
  309. 288.
    J. F. Morrison and E. Heyde, Ann. Rev. Biochem. 41:29 (1972).Google Scholar
  310. 289.
    A. S. Mildvan, Enzymes 2:446 (1970).Google Scholar
  311. 290.
    J. Imsande and P. Handler, Enzymes 5:281 (1961).Google Scholar
  312. 291.
    B. S. Cooperman in “Metal Ions in Biological Systems”, Vol. 5, H. Sigel, ed., Marcel Dekker, New York (1976).Google Scholar
  313. 292.
    A. S. Mildvan and G. M. Grisham, Structure and Bonding 1:20 (1974).Google Scholar
  314. 293.
    T. G. Spiro in “Inorganic Biochemistry”, Vol. 1, Chapter 17, G. L. Eichhorn, ed., Scientific Publishing Co., New York (1973).Google Scholar
  315. 294.
    P. J. Briggs, D. P. N. Satchell and G. F. White, J. Chem. Soc. (B), 1008 (1970).Google Scholar
  316. 295.
    D. E. Koshland, J. Am. Chem. Soc. 73:4103 (1951)Google Scholar
  317. D. E. Koshland, Idem, ibid. 74:2286 (1952).Google Scholar
  318. 296.
    J. L. Kurtz and C. D. Gutsche, J. Am. Chem. Soc. 82:2175 (1960).Google Scholar
  319. 297.
    G. D. Sabato and W. P. Jencks, J. Am. Chem. Soc. 83:4393, 4400 (1961).Google Scholar
  320. 298.
    C. H. Oestreich and M. M. Jones, Biochemistry 5:2926 (1966).Google Scholar
  321. 299.
    S. J. Benkovic and L. K. Dunikoski, Jr., J. Am. Chem. Soc. 93:1526 (1971).Google Scholar
  322. 300.
    R. H. Bromilow and A. J. Kirby, J. C. S. Perkin Trans. II 149 (1972).Google Scholar
  323. 301.
    R. Hofstetter, Y. Murakami, G. Mont and A. E. Martell, J. Am. Chem. Soc. 84:3041 (1962).Google Scholar
  324. 302.
    Y. Murakami and A. E. Martell, J. Am. Chem. Soc. 67:582 (1963).Google Scholar
  325. 303.
    J. D. Chanley, E. M. Gindler and H. Sobotka, J. Am. Chem. Soc. 74:4347 (1952);Google Scholar
  326. J. D. Chanley and E. M. Gindler, Ibid. 75:4035 (1953);Google Scholar
  327. J. D. Chanley and E. Feageson, Ibid. 77:4002 (1955).Google Scholar
  328. 304.
    M. L. Bender and J. M. Lawlor, J. Am. Chem. Soc. 85:3010 (1963).Google Scholar
  329. 305.
    C. H. Oestreich and M. M. Jones, Biochemistry 5:3151 (1966).Google Scholar
  330. 306.
    J. J. Stettens, E. J. Sampson, I. J. Siewers and S. J. Benkovic, J. Am. Chem. Soc. 95:936 (1973).Google Scholar
  331. 307.
    S. J. Benkovic and K. J. Schray, Biochemistry 7:4096 (1968).Google Scholar
  332. 308.
    Y. Murakami, J. Sunamoto and H. Sadamori, J. C. S. Chem. Commun. 983 (1969).Google Scholar
  333. 309.
    Y. Murakami and J. Sunamoto, Bull. Chem. Soc. Jpn. 44:1827 (1971).Google Scholar
  334. 310.
    Y. Murakami and M. Takagi, J. Am. Chem. Soc. 91:5130 (1969).Google Scholar
  335. 311.
    Y. Murakami, J. Sunamoto and H. Ishizu, Bull. Chem. Soc. Jpn. 45:590 (1972).Google Scholar
  336. 312.
    L. B. Nanninga, J. Phys. Chem. 61:1144 (1957).Google Scholar
  337. 313.
    C. M. Hsu and B. S. Cooperman, J. Am. Chem. Soc. 98:5652 (1976).Google Scholar
  338. 314.
    G. J. Lloyd, C. M. Hsu and B. S. Cooperman, J. Am. Chem. Soc. 93:4889 (1971).Google Scholar
  339. 315.
    W. P. Jencks and M. Gilchrist, J. Am. Chem. Soc. 87:3199 (1965).Google Scholar
  340. 316.
    J. J. Stettens, E. J. Sampson, I. J. Siewers and S. J. Benkovic, J. Am. Chem. Soc. 95:936 (1973).Google Scholar
  341. 317.
    V. M. Clark, A. R. Todd and S. G. Warren, Biochem. Z. 338:591 (1963).Google Scholar
  342. 318.
    S. J. Benkovic and E. M. Miller, Bioinorg. Chem. 1:107 (1972).Google Scholar
  343. 319.
    M. M. Taqui Khan and A. E. Martell, J. Am. Chem. Soc. 84:3037 (1962).Google Scholar
  344. 320.
    M. Tetas and J. M. Lowenstein, Biochemistry 2:350 (1963).Google Scholar
  345. 321.
    G. M. Woltermann, R. A. Scott and G. P. Haight, Jr., J. Am. Chem. Soc. 96:7569 (1974).Google Scholar
  346. 322.
    T. Wagner-Jauregg, B. E. Hackley, T. A. Lies, O. O. Owens and R. Proper, J. Am. Chem. Soc. 77:922 (1955).Google Scholar
  347. 323.
    F. M. Fowkes, G. S. Ronay and L. B. Ryland, J.Phys. Chem. 62:867 (1958).Google Scholar
  348. 324.
    R. C. Courtney, R. L. Gustafson, S. Westerback, H. Hyytiainen, S. Chaberek and A. E. Martell, J. Am. Chem. Soc. 79:3030 (1957).Google Scholar
  349. 325.
    R. L. Gustafson, S. Chaberek and A. E. Martell, J. Am. Chem. Soc. 85:598 (1963).Google Scholar
  350. 326.
    R. L. Gustafson and A. E. Martell, J. Am. Chem. Soc. 84:2309 (1962).Google Scholar
  351. 327.
    K. B. Augustinsson and G. Heimburger, Acta. Chem. Scand. 9:383 (1955).Google Scholar
  352. 328.
    F. J. Farrell, W. A. Kjellstrom and T. G. Spiro, Science 164:320 (1969).Google Scholar
  353. 329.
    E. A. Dennis and F. H. Westheimer, J. Am. Chem. Soc. 88:3422 (1966).Google Scholar
  354. 330.
    S. F. Lincoln and D. R. Stranks, Aust. J. Chem. 21:57 (1968).Google Scholar
  355. 331.
    B. Anderson, R. M. Milburn, J. MacB. Harrowfield, G. B. Robertson and A. M. Sargeson, J. Am. Chem. Soc. 99:2652 (1977).Google Scholar
  356. 332.
    A. Steitz and W. M. Lipscomb, J. Am. Chem. Soc. 87:2488 (1965).Google Scholar
  357. 333.
    C. L. Coulter, J. Am. Chem. Soc. 95:570 (1963).Google Scholar
  358. 334.
    S. Suzuki, S. Kimura, T. Higashiyama and A. Nakahara, Bioinorg. Chem. 3:183 (1974).Google Scholar
  359. 335.
    M. L. De Pamphilis and W. W. Cleland, Biochemistry 12:3714 (1973).Google Scholar
  360. 336.
    K. D. Danenberg and W. W. Cleland, Biochemistry 14:28 (1975).Google Scholar
  361. 337.
    C. A. Janson and W. W. Cleland, J. Biol. Chem. 249:2562, 2567, 2572 (1974);Google Scholar
  362. M. I. Schimerlik and W. W. Cleland, Ibid. 248:8418 (1973);Google Scholar
  363. D. A. Armbruster and F. B. Rudolph, Ibid. 251:32(1976);Google Scholar
  364. J. Bar-Tana and W. W. Cleland, Ibid. 249:1271 (1974).Google Scholar
  365. 338.
    R. D. Cornelius, P. A. Hart and W. W. Cleland, Inorg. Chem. 16:2799 (1977).Google Scholar
  366. 339.
    D. G. Gorenstein, J. Am. Chem. Soc. 97:898 (1975).Google Scholar
  367. 340.
    R. D. Cornelius, Inorg. Chem. 19:1286 (1980).Google Scholar
  368. 341.
    E. A. Merritt, M. Sundaralingam, R. D. Cornelius and W. W. Cleland, Biochemistry 17:3274 (1978).Google Scholar
  369. 342.
    P. W. A. Hubner and R. M. Milburn, Inorg. Chem. 19:1267 (1980).Google Scholar
  370. 343.
    S. F. Lincoln, J. Jayne and J. P. Hunt, Inorg. Chem. 8:2267 (1969).Google Scholar
  371. 344.
    E. Bamann, Angew.Chem. 52:186 (1939).Google Scholar
  372. 345.
    E. Bamann and M. Meisenheimer, Chem.Ber. 71:1711, 1980, 2086, 2233 (1938).Google Scholar
  373. 346.
    E. Bamann, F. Fischer and H. Trapmann, Biochem. Z. 325:413 (1951).Google Scholar
  374. 347.
    W. W. Butcher and F. H. Westheimer, J. Am. Chem. Soc. 77:2420 (1955).Google Scholar
  375. 348.
    H. Trapmann, Arzneimittel-Forsch. 9:341, 403 (1959).Google Scholar
  376. 349.
    J. L. Kice and J. M. Anderson, J. Am. Chem. Soc. 88:5242 (1966).Google Scholar
  377. 350.
    S. J. Benkovic and P. A. Benkovic, J. Am. Chem. Soc. 88:5504 (1966).Google Scholar
  378. 351.
    S. J. Benkovic J. Am. Chem. Soc. 88:5511 (1966).Google Scholar
  379. 352.
    R. W. Hay, C. R. Clark and J. A. G. Edmonds, J. C. S. Dalton Trans. 9 (1974).Google Scholar
  380. 353.
    K. S. Dodgson, B. Spencer and K. Williams, Biochem. J. 64:216 (1956).Google Scholar
  381. 354.
    K. S. Dodgson and B. Spencer, “Methods of Biochemical Analysis”, D. Gluck, ed., Vol. 4, p. 211, Interscience, New York (1956).Google Scholar
  382. 355.
    R. P. Hanzlik and W. J. Michaely, J.C.S.Chem.Commun. 113 (1975).Google Scholar
  383. 356.
    R. P. Hanzlik, M. Edelman, W. J. Michaely and G. Scott, J. Am. Chem. Soc. 98:1952 (1976).Google Scholar
  384. 357.
    J. N. DeMiller, Adv. Carbohydrate Chem. 22:25 (1967).Google Scholar
  385. 358.
    B. Capon, Chem. Rev. 69:407 (1969).Google Scholar
  386. 359.
    I. Wallenfels and P. O. Malhotra, Adv. Carbohydrate Chem. 16:239 (1960.Google Scholar
  387. 360.
    G. Low, Proc. Roy. Soc. (B) 167:431 (1967).Google Scholar
  388. 361.
    C. R. Clark and R. W. Hay, J.C.S.Perkin Trans. II: 1943 (1973).Google Scholar
  389. 362.
    R. J. Ferrier, R. W. Hay and N. Vethaviyasar, Carbohydrate Res. 27:55 (1973).Google Scholar
  390. 363.
    T. H. Fife and L. K. Jao, J. Org. Chem. 30:1492 (1965).Google Scholar
  391. 364.
    E. H. Cordes, Prog. Phys. Org. Chem. 4:1 (1967).Google Scholar
  392. 365.
    T. J. Przystas and T. H. Fife, J. Am. Chem. Soc. 102:4391 (1980).Google Scholar
  393. 366.
    J. G. Murphy, J. Pharm. Sci. 61:810 (1972).Google Scholar
  394. 367.
    W. W. Tilley, D. W. Porter and R. W. Gracy, Carbohydrate Res. 27:289 (1973).Google Scholar
  395. 368.
    E. A. Stein, J. Hsiu and E. H. Fischer, Biochemistry 3:56, 61 (1964).Google Scholar
  396. 369.
    For reviews see E. T. Kaiser and B. L. Kaiser, Accounts Chem. Res. 5:219 (1972);Google Scholar
  397. W. N. Lipscomb, Tetrahedron 30:1725 (1974).Google Scholar
  398. 370.
    R. Breslow, D. E. McClure, R. S. Brown and S. Eisenach, J. Am. Chem. Soc. 97:194 (1975).Google Scholar
  399. 371.
    J. W. Thanassi and T. C. Bruice, J. Am. Chem. Soc. 88:747 (1966);Google Scholar
  400. C. A. Bunton, N. A. Fuller, S. G. Perry and V. J. Shiner, J. Chem. Soc. 2918 (1963).Google Scholar
  401. 372.
    G. Tomalin, B. L. Kaiser and E. T. Kaiser, J. Am. Chem. Soc. 92:6046 (1970);Google Scholar
  402. P. L. Hall, B. L. Kaiser and E. T. Kaiser, Ibid. 91:485 (1969);Google Scholar
  403. E. T. Kaiser and F. W. Carson, ibid. 86:2922 (1966).Google Scholar
  404. 373.
    R. Breslow and D. Chipman, J. Am. Chem. Soc. 87:4195 (1965).Google Scholar
  405. 374.
    T. Sakan and Y. Mori, Chem. Lett. 793 (1972).Google Scholar
  406. 375.
    R. W. Hay and J. F. Ridlington, unpublished.Google Scholar
  407. 376.
    D. L. Leussing, “Metal Ions in Biological Systems”, H. Sigel, ed., Vol. 5, Marcel Dekker Inc., New York, p. 1 (1976).Google Scholar
  408. 377.
    G. L. Eichhorn and J. C. Bailar, J. Am. Chem. Soc. 75:2905 (1953).Google Scholar
  409. 378.
    G. L. Eichhorn and I. M. Trachtenberg, J. Am. Chem. Soc. 76:5183 (1954).Google Scholar
  410. 379.
    G. L. Eichhorn and N. D. Marchand, J. Am. Chem. Soc. 78:2688 (1956).Google Scholar
  411. 380.
    D. H. Busch and J. C. Bailar, J. Am. Chem. Soc. 78:1137 (1956).Google Scholar
  412. 381.
    D. F. Martin and F. F. Cantwell, J. Inorg. Nucl. Chem. 26:2219 (1964).Google Scholar
  413. 382.
    L. J. Nunez and G. L. Eichhorn, J. Am. Chem. Soc. 84:901 (1962).Google Scholar
  414. 383.
    D. L. Leussing and C. K. Stanfield, J. Am. Chem. Soc. 88:5726 (1966).Google Scholar
  415. 384.
    A. C. Dash and R. K. Nanda, J. Am. Chem. Soc. 91:6944 (1969).Google Scholar
  416. 385.
    L. F. Lindoy, Quart. Rev. Chem. Soc. 25:379 (1971).Google Scholar
  417. 386.
    C. M. Harris, S. L. Lenzer and R. L. Martin, Aust. J. Chem. 14:420 (1961).Google Scholar
  418. 387.
    R. W. Hay and P. R. Norman, unpublished observations.Google Scholar
  419. 388.
    A. C. Braithwaite, C.E.F. Rickard and T. N. Waters, J. C. S. Dalton Trans. 2149 (1975).Google Scholar
  420. 389.
    E. Hoyer and B. Lorenz, Z. Anorg. Allg. Chem. 336:192 (1965).Google Scholar
  421. 390.
    V. W. Skopenko and E. Hoyer, Z. Anorg. Allg. Chem. 339:214 (1965).Google Scholar
  422. 391.
    E. Hoyer, Naturwissenschaften 1 (1959).Google Scholar
  423. 392.
    E. Hoyer, Z. Chem. 231 (1965).Google Scholar
  424. 393.
    C. V. McDonnell, Diss. Abs. 28B:3242 (1968).Google Scholar
  425. 394.
    R. W. Hay and K. B. Nolan, J. C. S. Dalton Trans. 548 (1976).Google Scholar
  426. 395.
    J. M. Harrowfield and A. M. Sargeson, J. Am. Chem. Soc. 96:2634 (1974).Google Scholar
  427. 396.
    B. T. Golding, J. M. Harrowfield and A. M. Sargeson, J. Am. Chem. Soc. 96:3003 (1974).Google Scholar
  428. 397.
    B. T. Golding, J. M. Harrowfield, G. B. Robertson, A. M. Sargeson and P. O. Whimp, J. Am. Chem.Soc. 96:3691 (1974).Google Scholar
  429. 398.
    J. D. Bell, A. R. Gainsford, B. T. Golding, A. J. Herlt and A. M. Sargeson J. C. S. Chem. Commun. 980 (1974).Google Scholar
  430. 399.
    A. R. Gainsford and A. M. Sargeson, Aust. J. Chem. 31:1679 (1978).Google Scholar
  431. 400.
    D. A. Buckingham, J. M. Harrowfield and A. M. Sargeson, J. Am. Chem. Soc. 95:7281 (1973).Google Scholar
  432. 401.
    I. P. Evans, G. W. Everett, Jr. and A. M. Sargeson, J. C. S. Chem. Commun. 139 (1975).Google Scholar
  433. 402.
    K. Schug and C. P. Guengerich, J. Am.Chem.Soc. 97:4135 (1975).Google Scholar
  434. 403.
    D. Wayshort and G. Navon, J.C.S. Chem.Commun. 1410 (1971). This value may be erroneous;Google Scholar
  435. see J. N. Armor, J. Inorg. Nucl. Chem. 35:2067 (1973).Google Scholar
  436. 404.
    C. P. Guengerich and K. Schug, Inorg. Chem. 17:2819 (1978).Google Scholar
  437. 405.
    D. Hopgood, J. C. S. Dalton Trans. 482 (1972) and references therein.Google Scholar
  438. 406.
    T. C. Bruice and S J. Benkovic, “Bio-organic Mechanisms”, W. A. Benjamin, New York, Vol. 2, pp. 226–300 (1966).Google Scholar
  439. 407.
    S. Yamada, Y. Kuge and T. Yamayoshi, Inorg. Chim. Acta 8:29 (1974).Google Scholar
  440. 408.
    S. Yamada, Y. Kuge, T. Yamayoshi and H. Kuma, Inorg. Chim. Acta 11:253 (1974).Google Scholar
  441. 409.
    D. Heinert and A. E. Martell, J. Am. Chem. Soc. 85:1334 (1963).Google Scholar
  442. 410.
    For a discussion see “Coordination Chemistry of Macrocyclic Compounds”, G. A. Melson, ed., Plenum Press, New York (1979).Google Scholar
  443. 411.
    E. H. Cordes and W. P. Jencks, J. Am. Chem. Soc. 84:832 (1962).Google Scholar
  444. 412.
    L. J. Nunez and G. L. Eichhorn, J. Am. Chem. Soc. 84:901 (1962).Google Scholar
  445. 413.
    Y. Chauvin, D. Comereuc and F. Dawans, Progr. Polym. Sci. 5:95 (1977).Google Scholar
  446. 414.
    E. Tsuchi and H. Nishide, Advan. Polym. Sci. 24:1 (1977).Google Scholar
  447. 415.
    Y. Moriguchi, Bull. Chem. Soc. Jpn. 37:2656 (1966).Google Scholar
  448. 416.
    T. Nozawa, Y. Akimoto, and M. Hatano, Makromol.Chem. 158:21 (1972).Google Scholar
  449. 417.
    T. Nozawa, M. Hatano and S. Kanbara, Kogyo Kagaku Zasshi 72:373 (1969).Google Scholar
  450. 418.
    For a review of the catalytic activity of poly-L-lysine copper(II) complexes in the steroselective hydrolysis of amino-acid esters see M. Hatano and T. Nozawa in “Metal Ions in Biological Systems”, H. Sigel, ed., Vol 5. p. 245 et seq.Google Scholar
  451. 419.
    R. Breslow and L. E. Overman, J. Am. Chem. Soc. 92:1075 (1970).Google Scholar
  452. 420.
    R. L. Van Etten, J. F. Sebastian, G. A. Clowes and M. L. Bender, J. Am. Chem. Soc. 89:3242 (1967);Google Scholar
  453. R. L. Van Etten, J. F. Sebastian, G. A. Clowes and M. L. Bender, Idem. ibid. 89:3253 (1967).Google Scholar
  454. 421.
    N. E. Dixon and A. M. Sargeson in “Zinc Enzymes” T. G. Spiro, ed., John Wiley and Sons, New York, Chapter 7 (1983).Google Scholar
  455. 422.
    R. S. Brown, J. Huguet and N. J. Curtis, Met. Ions. Biol. Syst. 15:55 (1983).Google Scholar
  456. 423.
    R. W. Hay and P. Banerjee, J.C.S. Dalton Trans. 362 (1981).Google Scholar
  457. 424.
    R. W. Hay and A. K. Basak, J.C.S. Dalton Trans. 1819 (1982).Google Scholar
  458. 425.
    R. W. Hay and M. P. Pujari, J.C.S. Dalton Trans. 1083 (1984).Google Scholar
  459. 426.
    R. W. Hay and P. Banerjee, J.C.S. Dalton Trans. 2385 (1980).Google Scholar
  460. 427.
    R. W. Hay and P. Banerjee, J.C.S. Dalton Trans. 2452 (1980).Google Scholar
  461. 428.
    J. K. Walker and R. Nakon, Inorg. Chim. Acta 55:135 (1981).Google Scholar
  462. 429.
    R. W. Hay and P. Banerjee, J. Inorg. Biochem. 14:147 (1981).Google Scholar
  463. 430.
    A. Yeh and H. Taube, J. Am. Chem. Soc. 102:4725 (1980).Google Scholar
  464. 431.
    C. J. Boreham and D. A. Buckingham, Aust. J. Chem. 33:27 (1980).Google Scholar
  465. 432.
    C. J. Boreham and D. A. Buckingham, Inorg. Chem. 20:3112 (1981).Google Scholar
  466. 433.
    K. Ohkubo, K. Kawazoe and M. Toyoda, J. Mol. Catal. 9:219 (1980).Google Scholar
  467. 434.
    R. W. Hay and P. Banerjee, Inorg. Chim. Acta 44:L205 (1980).Google Scholar
  468. 435.
    W. N. Lipscombe, Acc. Chem. Res. 3:81 (1970).Google Scholar
  469. 436.
    R. W. Hay, “Bioinorganic Chemistry”, Ellis Horwood, Chichester (1984).Google Scholar
  470. 437.
    T. H. Fife and T. J. Przystas, J. Am. Chem. Soc. 104:2251 (1982).Google Scholar
  471. 438.
    J. Suh, M. Cheong and M. P. Suh, J. Am. Chem. Soc. 104:1654 (1982).Google Scholar
  472. 439.
    J. Suh, E. Lee and E. S. Jang, Inorg. Chem. 20:1932 (1982).Google Scholar
  473. 440.
    T. H. Fife and T. J. Przystas, J. Am. Chem. Soc. 102:7297 (1980).Google Scholar
  474. 441.
    T. H. Fife and T. J. Przystas, J. Am. Chem. Soc. 105:1638 (1983).Google Scholar
  475. 442.
    T. H. Fife and T. J. Przystas, J. Am. Chem. Soc. 107:1041 (1985).Google Scholar
  476. 443.
    R. S. Brown, M. Zamkanei and J. L. Cocho, J. Am. Chem. Soc. 106:5222 (1984).Google Scholar
  477. 444.
    R. S. Brown, D. Salmon, N. J. Curtis and S. Kusuma, J. Am. Chem. Soc. 104:3188 (1982).Google Scholar
  478. 445.
    K. Ogino, K. Shindo, T. Minami, W. Tagaki and T. Eiki, Bull. Chem. Soc. Jpn. 56:1101 (1983).Google Scholar
  479. 446.
    S. Sakaki, Y. Nakano and K. Ohkubo, Chem. Lett. 413 (1983).Google Scholar
  480. 447.
    D. A. Buckingham and C. R. Clark, Aust. J. Chem. 34:1769 (1981).Google Scholar
  481. 448.
    P. R. Norman and R. D. Cornelius, J. Am. Chem. Soc. 104:2356 (1982).Google Scholar
  482. 449.
    R. D. Cornelius and P. R. Norman, Inorg. Chim. Acta 65:L193 (1982).Google Scholar
  483. 450.
    E. A. Merritt and M. Sundaralingam, Acta. Cryst. B36:2576 (1980).Google Scholar
  484. 451.
    E. A. Merritt and M. Sundaralingam, Acta. Cryst. B37:1505 (1981).Google Scholar
  485. 452.
    E. A. Merritt, M. Sundaralingam and R. D. Cornelius, Acta. Cryst. B37:657 (1981).Google Scholar
  486. 453.
    D. R. Jones, L. F. Lindoy, A. M. Sargeson and M. R. Snow, Inorg. Chem. 21:4155 (1982).Google Scholar
  487. 454.
    R. W. Hay and R. Bembi, Inorg. Chim. Acta 78:143 (1983).Google Scholar
  488. 455.
    R. D. Cornelius, Inorg. Chim. Acta 46:L109 (1980).Google Scholar
  489. 456.
    P. R. Norman and R. D. Cornelius, Inorg. Chim. Acta 65:L193 (1982).Google Scholar
  490. 457.
    P. R. Norman, P. F. Gilletti and R. D. Cornelius, Inorg. Chim. Acta 82:L5 (1984).Google Scholar
  491. 458.
    J. Reibenspies and R. D. Cornelius, Inorg. Chem. 23:1563 (1984).Google Scholar
  492. 459.
    I. I. Creaser, G. P. Haight, R. Peachey, W. T. Robinson and A. M. Sargeson, J. C. S. Chem. Commun. 1568 (1984).Google Scholar
  493. 460.
    I. I. Creaser, R. V. Dubs and A. M. Sargeson, Aust. J. Chem. 37:1999 (1984).Google Scholar
  494. 461.
    W. G. Jackson and B. C. McGregor, Inorg. Chim. Acta 83:115 (1984).Google Scholar
  495. 462.
    P. Hendry and A. M. Sargeson, J. C. S. Chem. Commun. 164 (1984).Google Scholar
  496. 463.
    M. Hediger and R. M. Milburn, J. Inorg. Biochem. 16:165 (1982).Google Scholar
  497. 464.
    S. H. McClaugherty and C. M. Grisham, Inorg. Chem. 21:4133 (1982).Google Scholar
  498. 465.
    D. R. Jones, L. F. Lindoy and A. M. Sargeson, J. Am. Chem. Soc. 106:7807 (1984).Google Scholar
  499. 466.
    T. P. Haromy, P. F. Gilletti, R. D. Cornelius and M. Sundaralingam, J. Am. Chem. Soc. 106:2812 (1984).Google Scholar
  500. 467.
    D. R. Jones, L. F. Lindoy and A. M. Sargeson, J. Am. Chem. Soc. 105:7327 (1983).Google Scholar
  501. 468.
    J. MacB. Harrowfield, D. R. Jones, L. F. Lindoy and A. M. Sargeson, J. Am. Chem. Soc. 102:7733 (1980).Google Scholar
  502. 469.
    H. Sigel and F. Hofstetter, Eur. J. Biochem. 132:569 (1983).Google Scholar
  503. 470.
    T. Imamura, D. M. Hinton, R. L. Belford, R. I. Gumport and G. P. Haight, J. Inorg. Biochem. 11:241 (1979).Google Scholar
  504. 471.
    T. Eiki and W. Tagaki, Chem. Lett. 1465 (1981).Google Scholar
  505. 472.
    T. Eiki, T. Ogihara, A. Kato, F. Arai and W. Tagaki, J. C. S. Chem. Commun. 49 (1985).Google Scholar
  506. 473.
    W. Tagaki and T. Eiki, Adv. Chem. Ser. 191:407 (1980).Google Scholar
  507. 474.
    T. Eiki and W. Tagaki, Bull. Chem. Soc. Jpn. 55:1102 (1982).Google Scholar
  508. 475.
    T. Eiki, T. Horiguchi, M. Ono, S. Kawada and W. Tagaki, J. Am. Chem. Soc. 104:1986 (1982).Google Scholar
  509. 476.
    E. Buncel, E. J. Dunn, R.A.B. Bannard and J. G. Purdom, J.C.S. Chem. Commun. 162 (1984).Google Scholar
  510. 477.
    H. Sigel, F. Hofstetter, R. B. Martin, R. M. Milburn, V. SchellerKrattiger and K. H. Scheller, J. Am. Chem. Soc. 106:7935 (1984).Google Scholar
  511. 478.
    R. W. Hay and A. K. Basak, Inorg. Chim. Acta 79:255 (1983); see also ref. 543.Google Scholar
  512. 479.
    R. W. Hay, A. K. Basak, M. P. Pujari and A. Perotti, in preparation.Google Scholar
  513. 480.
    J. T. Groves and R. R. Chambers Jr., J. Am. Chem. Soc. 106:630 (1984).Google Scholar
  514. 481.
    Y. Ilan and H. Taube, Inorg. Chem. 22:3144 (1983).Google Scholar
  515. 482.
    Y. Ilan and H. taube, Inorg. Chem. 22:1655 (1983).Google Scholar
  516. 483.
    D. A. Buckingham, G. S. Binney, C. R. Clark, B. Garnham and J. Simpson, Inorg. Chem. 24:135 (1985).Google Scholar
  517. 484.
    D. A. Buckingham and C. R. Clark, Aust. J. Chem. 35:431 (1982).Google Scholar
  518. 485.
    R. W. Hay and R. Bembi, Inorg. Chim. Acta 64:L179 (1982).Google Scholar
  519. 486.
    C. J. Boreham, D. A. Buckingham, D. J. Francis, A. M. Sargeson and L. G. Warner, J. Am. Chem. Soc. 103:1975 (1981).Google Scholar
  520. 487.
    I. I. Creaser, J. MacB. Harrowfield, F. R. Keene and A. M. Sargeson, J. Am. Chem. Soc. 103:3559 (1981).Google Scholar
  521. 488.
    R. J. Balahura and W. L. Purcell, Inorg. Chem. 20:4159 (1981).Google Scholar
  522. 489.
    R. L. de la Vega, W. R. Ellis Jr. and W. L. Purcell, Inorg. Chim. Acta 68:97 (1983).Google Scholar
  523. 490.
    R. E. Clarke and P. C. Ford, Inorg. Chem. 9:227 (1970);Google Scholar
  524. P. C. Ford, J. C. S. Chem. Commun. 7 (1971).Google Scholar
  525. 491.
    N. J. Curtis, K. S. Hagen and A. M. Sargeson, J.C.S. Chem. Commun. 1571 (1984).Google Scholar
  526. 492.
    N. J. Curtis and A. M. Sargeson, J. Am. Chem. Soc. 106:625 (1984).Google Scholar
  527. 493.
    W. R. Ellis and W. L. Purcell, Inorg. Chem. 21:834 (1982).Google Scholar
  528. 494.
    W. Fleming, J. W. Fronabarger, M. L. Lieberman and V. M. Loyola, Second Chemical Conference of the North American Continent, Las Vegas, Nevada, August 1980, A.C.S., Washington D.C., Abstract INOR 13.Google Scholar
  529. 495.
    P. J. Lawson, M. G. McCarthy and A. M. Sargeson, J. Am.Chem. Soc. 104:6710 (1982).Google Scholar
  530. 496.
    N. E. Dixon and A. M. Sargeson, J. Am. Chem. Soc. 104:6716 (1982).Google Scholar
  531. 497.
    W. G. Jackson, G. M. McLaughlin, A. M. Sargeson and A. D. Watson, J. Am. Chem. Soc. 105:2426 (1983).Google Scholar
  532. 498.
    E. K. Chong, J. MacB. Harrowfield, W. G. Jackson, A. M. Sargeson and J. Springborg, J. Am. Chem. Soc. 107:2015 (1985).Google Scholar
  533. 499.
    H. Wautier, V. Daffe, M-N. Smets and J. Fastrez, J. C. S. Dalton Trans. 2479 (1981).Google Scholar
  534. 500.
    H. Wautier, D. Marchai and J. Fastrez, J.C.S. Dalton Trans. 2484 (1981).Google Scholar
  535. 501.
    C. R. Clark, R. F. Tasker, D. A. Buckingham, D. R. Knighton, D. R. K. Harding and W. S. Hancock, J. Am. Chem. Soc. 103:7023 (1981).Google Scholar
  536. 502.
    D. R. Knighton, D. R. K. Harding, M. J. Friar, W. S. Hancock, G. D. Reynolds, C. R. Clark, R. F. Tasker and D. A. Buckingham, J. Am. Chem. Soc. 103:7025 (1981).Google Scholar
  537. 503.
    S. S. Isied, A. Vassilian and J. M. Lyon, J. Am. Chem. Soc. 104:3910 (1982).Google Scholar
  538. 504.
    S. Bagger, I. Kristjansson, I. Sotof te and A. Thorlacius, Acta. Chem. Scand. A39:125 (1985).Google Scholar
  539. 505.
    N. E. Dixon, P. W. Riddles, C. Gazzola, R. L. Blakeley and B. Zerner, Can. J. Biochem. 58:1335 (1980).Google Scholar
  540. 506.
    R. L. Blakeley, A. Treston, R. K. Andrews and B. Zerner, J. Am. Chem. Soc. 104:612 (1982).Google Scholar
  541. 507.
    S. Suzuki, H. Narita and K. Harada, J.C.S. Chem. Commun. 29 (1979).Google Scholar
  542. 508.
    K. Aoka and H. Yamazaki, J.C.S. Chem. Commun. 363 (1980).Google Scholar
  543. 509.
    H. M. Dawes, J. M. Waters and T. N. Waters, Inorg. Chim. Acta 66:29 (1982).Google Scholar
  544. 510.
    J. R. Fischer and E. H. Abbott, J. Am. Chem. Soc. 101:2781 (1979).Google Scholar
  545. 511.
    H. C. Dunathan, Proc. Natl. Acad. Sci. U.S.A. 55:712 (1966).Google Scholar
  546. 512.
    L. Casella and M. Gullotti, J. Am. Chem. Soc. 103:6338 (1981).Google Scholar
  547. 513.
    L. Casella, M. Gullotti and G. Pacchoni, J. Am. Chem. Soc. 104:2386 (1982).Google Scholar
  548. 514.
    H. Kondo, H. Yoshinaga, K. Morita and J. Sunamoto, Chem. Lett. 31 (1982).Google Scholar
  549. 515.
    See for example J. A. Marcello, A. E. Martell and E. H. Abbott, J.C.S. Chem. Commun. 16 (1975).Google Scholar
  550. 516.
    J. A. Marcello and A. E. Martell, J. Am. Chem. Soc. 104:1087 (1982).Google Scholar
  551. 517.
    K. Tatsumoto, and A. E. Martell, J. Am. Chem. Soc. 103:6203(1981).Google Scholar
  552. 518.
    K. Tatsumoto, A. E. Martell and R. J. Motekartis, J. Am. Chem. Soc. 103:6197 (1981).Google Scholar
  553. 519.
    Y. N. Belokon, A. S. Melikyan, V. I. Bakhmutov, S. V. Vitt and V. M. Belikov, Inorg. Chim. Acta 55:117 (1981).Google Scholar
  554. 520.
    S.-B. Teo, S.-G. Teoh, J. R. Rodgers and M. R. Snow, J.C.S. Chem. Commun. 141 (1982).Google Scholar
  555. 521.
    S.-B. Teo and S.-G. Teoh, Inorg. Chim. Acta 91:L17 (1983).Google Scholar
  556. 522.
    S.-B. Teo and S.-G. Teoh, Inorg. Chim. Acta 68:107 (1983).Google Scholar
  557. 523.
    S.-B. Teo, S.-G. Teoh and M. R. Snow, Inorg. Chim. Acta 85:L1 (1984).Google Scholar
  558. 524.
    P. Sharrock, Polyhedron 2:111 (1983).Google Scholar
  559. 525.
    S.-B. Teo and M. J. O’Connor, Inorg. Chim. Acta 92:57 (1984).Google Scholar
  560. 526.
    G. G. Smith, A. Khatib and G. S. Reddy, J. Am. Chem. Soc. 105:293 (1983).Google Scholar
  561. 527.
    Y. N. Belokon, I. E. Sel’tzer, V. I. Bakmutov, M. B. Saporovskaya, M. G. Ryzhov, A. I. Yanovsky, Yu. T. Struchkov and V. M. Belikov, J. Am. Chem. Soc. 105:2010 (1983).Google Scholar
  562. 528.
    R. Deschenaux and K. Bernauer, Heiv. Chim. Acta 67:373 (1984).Google Scholar
  563. 529.
    K. Bernauer, R. Deschenaux and T. Taura, Hely. Chim. Acta 66:2049 (1983).Google Scholar
  564. 530.
    L. Casella, J. Gullotti and A. Rockenbauer, J.C.S. Dalton Trans. 1033 (1984).Google Scholar
  565. 531.
    A. E. Martell and P. Taylor, Inorg. Chem. 23:2734 (1984).Google Scholar
  566. 532.
    M. S. El-Ezaby and F. M. Al-Sogair, Polyhedron. 1:791 (1982).Google Scholar
  567. 533.
    B. Szpoganicz and A. E. Martell, Inorg. Chem. 23:4442 (1984).Google Scholar
  568. 534.
    M. S. El-Ezaby, M. Rashad and N. M. Moussa, Polyhedron 2:245 (1983).Google Scholar
  569. 535.
    L. R. Solujic, R. Herak, B. Prelesnik and M. B. Celap, Inorg. Chem. 24:32 (1985).Google Scholar
  570. 536.
    L. R. Solujic and M. B. Celap, Inorg. Chim. Acta 67:103 (1982).Google Scholar
  571. 537.
    Y. N. Belokon, V. I. Maleyev, S. V. Vitt, M. G. Ryzhov, Y. D. Kondrashov, S. N. Golubev, Y. P. Vauchskii, A. I. Kazika, M. I. Novikova, P. A. Kratsutski, A. G. Yurchenko, I. L. Dubchak, V. E. Shklover, Yu. T. Struchkov, V. I. Bakmutov and V. M. Belikov, J.C.S. Dalton Trans. 17 (1985).Google Scholar
  572. 538.
    P. D. Ford, K. B. Nolan and D. C. Povey, Inorg. Chim. Acta 61:189 (1982).Google Scholar
  573. 539.
    A. R. Gainsford, R. D. Pizer, A. M. Sargeson and P. O. Whimp, J. Am. Chem. Soc. 103:792 (1981).Google Scholar
  574. 540.
    A. C. Dash, B. Dash and S. Praharaj, J.C.S. Dalton Trans. 2063 (1981).Google Scholar
  575. 541.
    U. Bips, H. Elias, M. Hauroder, G. Kleinhaus, S. Pfeifer and K. J. Wannowius, Inorg. Chem. 22:3862 (1983).Google Scholar
  576. 542.
    R. W. Hay, V.M.C. Reid and D.P. Piplani, Transition Met. Chem. 11:302 (1986).Google Scholar
  577. 543.
    R. W. Hay, A. K. Basak, M. P. Pujari and A. Perotti, J.C.S. Dalton Trans. 2029 (1986).Google Scholar

Copyright information

© Plenum Press, New York 1989

Authors and Affiliations

  • Robert W. Hay
    • 1
  1. 1.Department of ChemistryUniversity of StirlingUK

Personalised recommendations