Advertisement

Examples of Reactions Catalysed by Acids and Bases

  • R. P. Bell

Abstract

Any comprehensive account of reactions catalysed by acids and bases would cover a large proportion of organic chemistry and biochemistry, and would demand at least a whole book; in fact, two excellent books giving a general coverage of the subject have recently appeared.1,2 This chapter will be devoted to a fairly detailed consideration of a small number of reactions, chosen so as to illustrate the variety of kinetic behaviour forecast by the general treatment in the last chapter. They will also show in small measure the variety of chemical change which can result from the removal or addition of a proton. Some of the work described involves a study of series of acidic or basic catalysts, and some mention will be made of the relation of catalytic activity to acid-base strength, though a full treatment of this topic will be deferred until Chapter 10. Similarly, hydrogen isotope effects will be mentioned when they throw light on the mechanism of the reaction, but will not be considered quantitatively until Chapter 12.

Keywords

Acid Catalysis Base Catalysis Catalytic Constant Electrophilic Aromatic Substitution Ethyl Diazoacetate 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    W. P. Jencks, Catalysis in Chemistry and Biochemistry, McGraw-Hill, New York, 1969.Google Scholar
  2. 2.
    M. L. Bender, Mechanism of Homogeneous Catalysis from Protons to Proteins, Wiley-Interscience, New York, 1971.Google Scholar
  3. 3.
    J. N. Brönsted and K. J. Pedersen, Z. Phys. Chem., 108, 185 (1924).Google Scholar
  4. 4.
    S. Tellier-Pollon and J. Heubel, Rev. Chim. Minérale, 4, 413 (1967).Google Scholar
  5. 5.
    A. Avorio, Decomposizione Catalytica della Nitramide, F. Centenari, Rome, 1937.Google Scholar
  6. 6.
    J. Thiele and A. Lachmann, Annalen, 288, 267 (1895).Google Scholar
  7. 7.
    A. Hantzsch, Annalen, 292, 340 (1896).Google Scholar
  8. 8.
    A. Hantzsch, Ber., 63, 1270 (1930).Google Scholar
  9. 9.
    E. C. E. Hunter and J. R. Partington, J. Chem. Soc., 309 (1933).Google Scholar
  10. 10.
    M. Davies and N. Jonathan, Trans. Faraday Soc., 54, 469 (1958).CrossRefGoogle Scholar
  11. 11.
    J. D. Ray and R. A. Ogg, J. Chem. Phys., 26, 1452 (1957).CrossRefGoogle Scholar
  12. 12.
    J. K. Tyler, J. Mol. Spectroscopy, 11, 39 (1963).CrossRefGoogle Scholar
  13. 13.
    L. K. J. Tong and A. R. Olson, J. Am. Chem. Soc., 63, 3406 (1941); cf. J. N. Brönsted and C. V. King, J. Am. Chem. Soc., 49, 193 (1927).Google Scholar
  14. 14.
    V. K. La Mer and S. Hochberg, J. Am. Chem. Soc., 61, 2552 (1939).CrossRefGoogle Scholar
  15. 15.
    K. J. Pedersen, J. Phys. Chem., 38, 581 (1934).CrossRefGoogle Scholar
  16. 16.
    K. Clusius, Hely. Chim. Acta, 44, 1149 (1961).CrossRefGoogle Scholar
  17. 17.
    P. Vast, Bull. Soc. Chim. France, 2136 (1970).Google Scholar
  18. 18.
    C. A. Marlies and V. K. LaMer, J. Am. Chem. Soc., 57, 1812 (1935).CrossRefGoogle Scholar
  19. 19.
    V. Beretta, Rend. Accad. Sei. Napoli, 8, 36 (1938).Google Scholar
  20. 20.
    R. P. Bell and E. C. Baughan, Proc. Roy. Soc., A, 158, 464 (1937).CrossRefGoogle Scholar
  21. 21.
    R. P. Bell and G. M. Waind, J. Chem. Soc., 2357 (1951).Google Scholar
  22. 22.
    R. P. Bell and J. C. McCoubrey, Proc. Roy. Soc., A, 234, 192 (1956).CrossRefGoogle Scholar
  23. 23.
    B. Perlmutter-Hayman and M. A. Wulff, Israel J. Chem., 153 (1969).Google Scholar
  24. 24.
    R. P. Bell, B. G. Cox, and B. A. Timimi, J. Chem. Soc., B, 2247 (1971).Google Scholar
  25. 25.
    R. P. Bell, B. G. Cox, and J. B. Henshall, J. Chem. Soc., Perk. Trans. 2, 1232 (1972).Google Scholar
  26. 26.
    J. N. Brönsted and H. C. Duus, Z. Phys. Chem., 117, 299 (1925).Google Scholar
  27. 27.
    J. N. Brönsted and K. Volqvartz, Z. Phys. Chem., 155, A, 211 (1931).Google Scholar
  28. 28.
    L. K. J. Tong and A. R. Olson, J. Am. Chem. Soc., 63, 3406 (1941).CrossRefGoogle Scholar
  29. 29.
    R. P. Bell and G. L. Wilson, Trans. Faraday Soc., 46, 407 (1950).CrossRefGoogle Scholar
  30. 30.
    V. K. LaMer and J. Greenspan, Trans. Faraday Soc., 33, 1266 (1937).CrossRefGoogle Scholar
  31. 31.
    S. Liotta and V. K. LaMer, J. Am. Chem. Soc., 60, 1967 (1938).CrossRefGoogle Scholar
  32. 32.
    N. Brönsted and J. E. Vance, Z. Phys. Chem., 163, A, 240 (1933).Google Scholar
  33. 33.
    J N. Brönsted, A. L. Nicholson, and A. Delbanco, Z. Phys. Chem., 169, A, 379 (1934).Google Scholar
  34. 34.
    W. W. Carnie, P. M. Duncan, J. A. Kerr, K. Shannon, and A. F. TrotmanDickenson, J. Chem. Soc., 3231 (1959).Google Scholar
  35. 35.
    A. Voipio, Suomen Kern., 29, B, 170 (1956); 30, A, 72 (1957); Ann. Acad. Sci. Fennicae, A, No. 92 (1958).Google Scholar
  36. 36.
    R. P. Bell and A. F. Trotman-Dickenson, J. Chem. Soc., 1288 (1949).Google Scholar
  37. 37.
    R. P. Bell and E. F. Caldin, Trans. Faraday Soc., 47, 50 (1951).CrossRefGoogle Scholar
  38. 38.
    G. C. Fettis, J. A. Kerr, A. McClure, J. S. Slater, C. Steel, and A. F. TrotmanDickenson, J. Chem. Soc., 2811 (1957).Google Scholar
  39. 39.
    E. F. Caldin and J. Peacock, Trans. Faraday Soc., 51, 1217 (1955).CrossRefGoogle Scholar
  40. 40.
    D. D. Callander, W. D. Ferguson, G. C. Fettis, and A. F. Trotman-Dickenson, J. Chem. Soc., 3834 (1960).Google Scholar
  41. 41.
    R. A. More O’Ferrall, Adv. Phys. Org. Chem., 5, 331 (1967).CrossRefGoogle Scholar
  42. 42.
    W. J. Albery, J. E. C. Hutchins, R. M. Hyde, and R. H. Johnson, J. Chem. Soc., B, 219 (1968).Google Scholar
  43. 43.
    W. J. Albery and M. H. Davies, Trans. Faraday Soc., 65, 1066 (1969).CrossRefGoogle Scholar
  44. 44.
    G. Bredig and R. F. Ripley, Ber., 40, 4015 (1907).Google Scholar
  45. 45.
    H. Lachs, Z. Phys. Chem., 73, 291 (1910).Google Scholar
  46. 46.
    G. Bredig and W. Fraenkel, Z. Elektrochem., 11, 525 (1905).CrossRefGoogle Scholar
  47. 47.
    W. Fraenkel, Z. Phys. Chem., 60, 202 (1907).Google Scholar
  48. 48.
    E. Spitalsky, Z. Anorg. Chem., 54, 278 (1907).CrossRefGoogle Scholar
  49. 49E.
    A. Moelwyn-Hughes and P. Johnson, Trans. Faraday Soc., 37, 282 (1941).CrossRefGoogle Scholar
  50. 50.
    J N. Brönsted and C. E. Teeter, J. Phys. Chem., 28, 579 (1924); J. N. Brönsted and H. Duus, Z. Phys. Chem., 117, 299 (1925); J. N. Brönsted and C. V. King, Z. Phys. Chem., 130, 699 (1927); J. N. Brönsted and K. Volquartz, Z. Phys. Chem., 134, 97 (1928).Google Scholar
  51. 51.
    H. C. S. Snethlage, Z. Elektrochem., 18, 539 (1912).Google Scholar
  52. 52.
    P. Gross and A. Goldstern, Monatsh., 55, 316 (1930).CrossRefGoogle Scholar
  53. 53.
    J. W. Woolcock and H. B. Hartley, Phil. Mag., (vii) 5, 1133 (1928).Google Scholar
  54. 54.
    J. D. Roberts and W. Watanabe, J. Am. Chem. Soc., 72, 4869 (1950).CrossRefGoogle Scholar
  55. 55.
    P. Gross, H. Steiner, and F. Krauss, Trans. Faraday Soc., 34, 351 (1938).CrossRefGoogle Scholar
  56. 56.
    J. D. Roberts, C. M. Regan, and I. Allen, J. Am. Chem. Soc., 74, 3679 (1952).CrossRefGoogle Scholar
  57. 57.
    W. J. Albery and R. P. Bell, Trans. Faraday Soc., 57, 1941 (1961).CrossRefGoogle Scholar
  58. 58.
    J. D. Roberts, E. A. McElhill, and R. Armstrong, J. Am. Chem. Soc., 71, 2923 (1949).Google Scholar
  59. 59.
    J. D. Roberts and W. Watanabe, J. Am. Chem. Soc., 72, 4869 (1950).CrossRefGoogle Scholar
  60. 60.
    J. D. Roberts and R. H. Mazur, J. Am. Chem. Soc., 73, 2509 (1951).CrossRefGoogle Scholar
  61. 61.
    J. D. Roberts, W. Watanabe, and R. E. McMahon, J. Am. Chem. Soc., 73, 760, 2521 (1951).CrossRefGoogle Scholar
  62. 62.
    J. D. Roberts and C. M. Regan, Analyt. Chem., 24, 360 (1952); J. Am. Chem. Soc., 74, 3695 (1952).Google Scholar
  63. 63.
    J. D. Roberts, C. M. Regan, and I. Allen, J. Am. Chem. Soc., 74, 3679 (1952).CrossRefGoogle Scholar
  64. 64.
    K. Bowden, A. Buckley, and N. B. Chapman, J. Chem. Soc., 3380 (1964).Google Scholar
  65. 65.
    R. A. More O’Ferrall, Wo Kong Kwok, and S. I. Miller, J. Am. Chem. Soc., 86, 5553 (1964).CrossRefGoogle Scholar
  66. 66.
    For the reaction with benzoic acid in 42 solvents, see N. B. Chapman, M. R. J. Dack, and J. Shorter, J. Chem. Soc.,B, 834 (1971), and earlier papers.Google Scholar
  67. 67.
    C. V. King and E. D. Bolinger, J. Am. Chem. Soc., 58, 1533 (1936).CrossRefGoogle Scholar
  68. 68.
    R. P. Bell and P. T. McTigue, J. Chem. Soc., 2983 (1960).Google Scholar
  69. 69.
    M. M. Kreevoy and D. E. Konasewich, J. Phys. Chem., 74, 4464 (1970): Adv. Chem. Phys., 21, 243 (1971).Google Scholar
  70. 70.
    B. Zwanenburg and J. B. F. N. Engberts, Rec. Tray. Chim., 84, 165 (1965); J. B. F. N. Engberts, G. Zuidema, B. Zwanenburg, and J. Strating, Rec. Tray. Chim., 88, 641 (1969).Google Scholar
  71. 71.
    C. E. McCauley and C. V. King, J. Am. Chem. Soc., 74, 6221 (1952); H. Dahn, and H. Gold, Hell. Chim. Acta, 56, 983 (1963; H. Dahn, A. Donzel, A. Merbach, and H. Gold, Heir. Chim. Acta, 56, 994 (1963).Google Scholar
  72. 72.
    H. Dahn, H. Gold, M. Ballenegger, J. Lenoir, G. Diderich, and R. Malherbe, Heir. Chim. Acta, 51, 2065 (1968).CrossRefGoogle Scholar
  73. 73.
    H. Dahn and M. Ballenegger, Hely. Chim. Acta, 52, 2417 (1969).CrossRefGoogle Scholar
  74. 74.
    W. J. Albery, A. N. Campbell-Crawford, and K. S. Hobbs, J. Chem. Soc. Perkin Trans. II, 2180 (1972).Google Scholar
  75. 75.
    H. Dahn and G. Diderich, Heiv. Chico. Acta, 54, 1950 (1971); G. Diderich and H. Dahn, Heir. Chim. Acta, 55, 1 (1972).Google Scholar
  76. 76.
    J. B. F. N. Engberts, N. F. Bosch, and B. Zwanenburg, Rec. Tray. Chim.,85 1068 Ç1966).Google Scholar
  77. 77.
    C. V. King and P. Kulka, J. Am. Chem. Soc., 72, 1906 (1950); C. V. King, P. Kulka, and A. Mebane, J. Am. Chem. Soc., 74, 3128 (1952).Google Scholar
  78. 78.
    C. V. King, J. Am. Chem. Soc., 62, 379 (1940); C. V. King and J. J. Josephs, J. Am. Chem. Soc., 66, 767 (1944).Google Scholar
  79. 79.
    H. M. Dawson and F. Powis, J. Chem. Soc., 2135 (1913).Google Scholar
  80. 80.
    C. K. Ingold, Structure and Mechanism in Organic Chemistry, 2nd edn., Bell, London, 1969, p. 835.Google Scholar
  81. 81.
    A. Lapworth, J. Chem. Soc., 30 (1904).Google Scholar
  82. 82.
    H. M. Dawson and F. Powis, J. Chem. Soc., 2135 (1913): H. M. Dawson and C. K. Reiman, J. Chem. Soc., 1426 (1915); H. M. Dawson and N. C. Dean, J. Chem. Soc., 2872 (1926); H. M. Dawson and C. R. Hoskins, J. Chem. Soc., 3166 (1926); H. M. Dawson, J. Chem. Soc., 213, 756, 1146 (1927); H. M. Dawson and A. Key, J. Chem. Soc., 543, 1239, 1248 (1928); H. M. Dawson, G. V. Hall, and A. Key, J. Chem. Soc., 2844 (1928); H. M. Dawson, C. R. Hoskins, and J. E. Smith, J. Chem. Soc., 1884 (1929): F. O. Rice and H. C. Urey, J. Am. Chem. Soc., 52, 95 (1930); G. F. Smith, J. Chem. Soc., 1744 (1934); R. P. Bell and O. M. Lidwell, Proc. Roy. Soc., A, 176. 88 (1940).Google Scholar
  83. 83.
    J. A. Feather and V. Gold, J. Chem. Soc., 1752 (1965).Google Scholar
  84. 84.
    M. L. Bender and A. Williams, J. Am. Chem. Soc., 88, 2504 (1966).Google Scholar
  85. 85.
    R. P. Bell and J. E. Prue, Trans. Faraday Soc., 46, 5 (1950).CrossRefGoogle Scholar
  86. 86.
    P. D. Bartlett and J. R. Vincent, J. Am. Chem. Soc., 57, 1596 (1935).CrossRefGoogle Scholar
  87. 87.
    R.-R. Li and S. I. Miller, J. Chem. Soc., B, 2269 (1971).Google Scholar
  88. 88.
    R. P. Bell and H. C. Longuet-Higgins, J. Chem. Soc., 636 (1946).Google Scholar
  89. 89.
    J. R. Jones, Trans. Faraday Soc., 61, 65 (1965); 65, 2138 (1969).Google Scholar
  90. 90.
    K. J. Pedersen, J. Phys. Chem., 37, 751 (1933); 38, 601 (1934).Google Scholar
  91. 91.
    R. P. Bell and O. M. Lidwell, Proc. Roy. Soc., A, 176, 88 (1940).CrossRefGoogle Scholar
  92. 92.
    R. P. Bell, D. H. Everett, and H. C. Longuet-Higgins, Proc. Roy. Soc., A, 186, 433 (1946).Google Scholar
  93. 93.
    R. P. Bell, R. D. Smith, and L. A. Woodward, Proc. Roy. Soc., A, 192, 479 (1948).CrossRefGoogle Scholar
  94. 94.
    R. P. Bell, E. Gelles, and E. Möller, Proc. Roy. Soc., A, 198, 310 (1949).Google Scholar
  95. 95.
    R. P. Bell and H. L. Goldsmith, Proc. Roy. Soc., A, 216, 322 (1952).Google Scholar
  96. 96.
    R. P. Bell and T. Spencer, Proc. Roy. Soc., A, 251, 41 (1959).CrossRefGoogle Scholar
  97. 97.
    R. P. Bell and J. Hansson, Proc. Roy. Soc., A, 255, 214 (1960).CrossRefGoogle Scholar
  98. 98.
    R. P. Bell and G. A. Wright. Trans. Faraday Soc., 57, 1386 (1961).CrossRefGoogle Scholar
  99. 99.
    R. P. Bell and R. R. Robinson, Proc. Roy. Soc., A, 270, 411 (1962).CrossRefGoogle Scholar
  100. 100.
    T. Riley and F. A. Long, J. Am. Chem. Soc., 84, 522 (1962).CrossRefGoogle Scholar
  101. 101.
    R. P. Bell and J. E. Crooks, Proc. Roy. Soc., A, 286, 285 (1965).CrossRefGoogle Scholar
  102. 102.
    J. A. Feather and V. Gold, J. Chem. Soc., 1752 (1965).Google Scholar
  103. 103.
    R. P. Bell and H. F. F. Ridgewell, Proc. Roy. Soc., A, 298, 178 (1967).CrossRefGoogle Scholar
  104. 104.
    G E. Lienhard and Tung-Chia Wang, J. Am. Chem. Soc., 91, 1146 (1969).CrossRefGoogle Scholar
  105. 105.
    R. P. Bell and P. de Maria, Trans. Faraday Soc., 66, 930 (1970).CrossRefGoogle Scholar
  106. 106.
    R. P. Bell and D. J. Barnes, Proc. Roy. Soc., A, 318, 421 (1970).CrossRefGoogle Scholar
  107. 107.
    G E. Lienhard and F. H. Anderson, J. Org. Chem., 32, 2229 (1967).CrossRefGoogle Scholar
  108. 108.
    L. Zucker and L. P. Hammett, J. Am. Chem. Soc., 61, 2785 (1939).CrossRefGoogle Scholar
  109. 109.
    P Salomaa, A. Kankaaperä, and M. Lajunen, Acta Chem. Scand., 20, 1790 (1966): A. J. Kresge and Y. Chiang, J. Chem. Soc., B, 53 (1967): M. M. Kreevoy and R. Eliason, J. Phys. Chem., 72, 1313 (1968).Google Scholar
  110. 110.
    J. E. Dubois and J. Toullec, Chem. Comm., 478 (1969).Google Scholar
  111. 111.
    R. P. Bell and E. F. Caldin, J. Chem. Soc., 382 (1938): R. P. Bell, O. M. Lidwell, and J. Wright, J. Chem. Soc., 1861 (1938).Google Scholar
  112. 112.
    O. Reitz, Z. Phys. Chem., A, 179, 119 (1936).Google Scholar
  113. 113.
    See T. C. Bruice and S. J. Benkovic, Bioorganic Mechanisms,Vol. 1, pp. 119ff., Benjamin, New York, 1966; W. P. Jencks, Catalysis in Chemistry and Enzymology,McGraw-Hill, New York, 1969, Ch. 1.Google Scholar
  114. 114.
    R. P. Bell and M. A. D. Fluendy, Trans. Faraday Soc., 59, 1623 (1963).CrossRefGoogle Scholar
  115. 115.
    J. K. Coward and T. C. Bruice, J. Am. Chem. Soc., 91, 5339 (1969).CrossRefGoogle Scholar
  116. 116.
    R. P. Bell and B. A. Timimi, to be published.Google Scholar
  117. 117.
    E. T. Harper and M. L. Bender, J. Am. Chem. Soc., 87, 5625 (1965).CrossRefGoogle Scholar
  118. 118.
    R. P. Bell, B. G. Cox, and J. B. Henshall, J. Chem. Soc., Perk. Trans. 2, 1232 (1972).Google Scholar
  119. 119.
    Page and W. P. Jencks, Proc. Nat. Acad. Sci., 68, 1671 (1971).Google Scholar
  120. 120.
    R. P. Bell and G. G. Davis, J. Chem. Soc., 902 (1962).Google Scholar
  121. 121.
    R. P. Bell and K. Yates, J. Chem. Soc., 1927 (1962).Google Scholar
  122. 122.
    R. P. Bell and M. Spiro, J. Chem. Soc., 429 (1953).Google Scholar
  123. 123.
    R. P. Bell and D. J. Rawlinson, J. Chem. Soc., 726 (1961).Google Scholar
  124. 124.
    R. P. Bell and B. G. Cox, J. Chem. Soc., B, 654 (1971).Google Scholar
  125. 125.
    R. P. Bell and E. Gelles, Proc. Roy. Soc., A, 210, 310 (1952).CrossRefGoogle Scholar
  126. 126.
    R. P. Bell and P. Engel, J. Chem. Soc., 247 (1957).Google Scholar
  127. 127.
    R. P. Bell and D. C. Vogelsong, J. Chem. Soc., 243 (1958).Google Scholar
  128. 128.
    D. R. Marshall and T. R. Roberts, J. Chem. Soc., B, 797 (1971).Google Scholar
  129. 129.
    R. P. Bell and D. J. Rawlinson, J. Chem. Soc., 726 (1961).Google Scholar
  130. 130.
    A. J. Green, T. J. Kemp, J. S. Littler, and W. A. Waters, J. Chem. Soc., 2722 (1964).Google Scholar
  131. 131.
    R. P. Bell, J. Chem. Soc., 1637 (1937); A. Broche, Colloque Nationale de Cinétique, Strasbourg, 1953; A. Broche and R. Gibert, Bull. Soc. Chim. France, 131 (1955); R. P. Bell and P. T. McTigue, J. Chem. Soc., 2983 (1960); L. C. Gruen and P. T. McTigue, Austral. J. Chem., 17, 953 (1964).Google Scholar
  132. 132.
    K. F. Bonhoeffer and W. D. Walters, Z. Phys. Chem., 181, 441 (1938).Google Scholar
  133. 133.
    R. P. Bell and M. J. Smith, J. Chem. Soc., 1691 (1958).Google Scholar
  134. 134.
    R. P. Bell and P. T. McTigue (131); Y. Ogata, A. Kawasaki, and K. Y.koi, J. Chem. Soc., B, 1013 (1967); P. T. McTigue, J. Kirsanova, and H. Tankey, J. Austral. Chem., 17, 499 (1964).Google Scholar
  135. 135.
    M. L. Bender, Chem. Rev., 60, 53 (1960).CrossRefGoogle Scholar
  136. 136.
    W. P. Jencks, Progr. Phys. Org. Chem., 2, 63 (1964).CrossRefGoogle Scholar
  137. 137.
    S. Johnson, Adv. Phys. Org. Chem., 5, 237 (1967).CrossRefGoogle Scholar
  138. 138.
    For a review, see R. P. Bell, Adv. Phys. Org. Chem., 4, 1 (1966).CrossRefGoogle Scholar
  139. 139.
    W. H. Perkin, J. Chem. Soc., 808 (1887); H. T. Brown and P. S. U. Pickering, J. Chem. Soc., 774 (1897).Google Scholar
  140. 140.
    R. P. Bell and W. C. E. Higginson, Proc. Roy. Soc., A, 197, 141 (1949).CrossRefGoogle Scholar
  141. 141.
    R. P. Bell and B. de B. Darwent, Trans. Faraday Soc., 46, 34 (1950).CrossRefGoogle Scholar
  142. 142.
    R. P. Bell and J. C. Clunie, Proc. Roy. Soc., A, 212, 33 (1952).CrossRefGoogle Scholar
  143. 143.
    R. P. Bell, M. H. Rand, and K. M. A. Wynne-Jones, Trans. Faraday Soc., 52, 1093 (1956).CrossRefGoogle Scholar
  144. 144.
    L. C. Gruen and P. T. McTigue, J. Chem. Soc., 5224 (1963).Google Scholar
  145. 145.
    Y Pocker and D. G. Dickerson, J. Phys. Chem., 73, 405 (1969).Google Scholar
  146. 146.
    P G. Evans, M. M. Kreevoy, and G. R. Miller, J. Phys. Chem., 69, 4325 (1965).CrossRefGoogle Scholar
  147. 147.
    M.-L. Ahrens and H. Strehlow, Disc. Faraday Soc., 39, 112 (1965).CrossRefGoogle Scholar
  148. 148.
    J. Hine and J. G. Houston, J. Org. Chem., 30, 1328 (1965).CrossRefGoogle Scholar
  149. 149.
    P Greenzaid, Z. Luz, and D. Samuel, J. Am. Chem. Soc., 89, 756 (1967).CrossRefGoogle Scholar
  150. 150.
    R. Brdicka, Coll. Czech. Chem. Comm., 20, 387 (1955).Google Scholar
  151. 151.
    P. L. Hénaff, Compt. Rend., 256, 1752 (1963).Google Scholar
  152. 152.
    R. P. Bell and P. G. Evans, Proc. Roy. Soc., A, 291, 297 (1966).CrossRefGoogle Scholar
  153. 153.
    P E. Sörensen, Acta Chem. Scand., 26, 3357 (1972).CrossRefGoogle Scholar
  154. 154.
    M. Eigen, Disc. Faraday Soc., 39, 7 (1965).CrossRefGoogle Scholar
  155. 155.
    M. Anbar, A. Loewenstein, and S. Meiboom, J. Am. Chem. Soc., 80, 2630 (1958).CrossRefGoogle Scholar
  156. 156.
    E. Grunwald, C. F. Jumper, and S. Meiboom, J. Am. Chem. Soc., 85, 522 (1963); E. Grunwald and S. Meiboom, J. Am. Chem. Soc., 85, 2047 (1963); Z. Luz and S. Meiboom, J. Am. Chem. Soc., 85, 3923 (1963).Google Scholar
  157. 157.
    R. P. Bell and M. B. Jensen, Proc. Roy. Soc., A, 261, 38 (1961).CrossRefGoogle Scholar
  158. 158.
    R. P. Bell, J. F. Millington, and J. M. Pink, Proc. Roy. Soc., A, 303, 1 (1968).CrossRefGoogle Scholar
  159. 159.
    R. P. Bell and P. E. Sörensen, J. Chem. Soc., Perk. Trans. 2, 1740 (1972).Google Scholar
  160. 160.
    R. P. Bell and J. E. Critchlow, Proc. Roy. Soc., A, 325, 35 (1971).CrossRefGoogle Scholar
  161. 161.
    J. T. Edsall and J. Wyman, Biophysical Chemistry,Academic Press, New York, 1958, Vol. I, Ch. 10.Google Scholar
  162. 162.
    A. Sharma and P. V. Danckwerts, Trans. Faraday Soc., 59, 386 (1963).CrossRefGoogle Scholar
  163. 163.
    C. Ho and J. M. Sturtevant, J. Biol. Chem., 238, 3499 (1963).Google Scholar
  164. l64.
    B. H. Gibbons and J. T. Edsall, J. Biol. Chem., 238, 3502 (1963).Google Scholar
  165. 165.
    J. C. Kernohan, Biochim. Biophys. Acta, 81, 346 (1964).Google Scholar
  166. 166.
    J. Pocker and J. E. Meany, J. Am. Chem. Soc., 87, 1809 (1965); J. Phys. Chem., 71, 3113 (1967); 72, 655 (1968); Biochemistry, 4, 2535 (1965); 6, 239 (1967).Google Scholar
  167. 167.
    G. W. Meadows and B. de B. Darwent, Trans. Faraday Soc., 48, 1015 (1952).CrossRefGoogle Scholar
  168. 168.
    R. P. Bell and D. G. Horne, J. Chem. Soc., Perk. Trans. 2, 1371 (1972).Google Scholar
  169. 169.
    R. P. Bell and E. C. Baughan, J. Chem. Soc., 1947 (1937).Google Scholar
  170. 170.
    R. P. Bell and J. P. H. Hirst, J. Chem. Soc., 1777 (1939).Google Scholar
  171. 171.
    A. McKenzie and A. G. Mitchell, Biochem. Z., 208, 456 (1929): A. McKenzie and P. D. Ritchie, Biochem. Z., 231, 412 (1931); 237, 1 (1931); 250, 376 (1932).Google Scholar
  172. 172.
    R. Alquier, Bull. Soc. Chim. France, (5)10, 197 (1943).Google Scholar
  173. 173.
    J. R. Schaefgen, F. H. Verhoek, and M. S. Newman, J. Am. Chem. Soc., 67, 253 (1945).CrossRefGoogle Scholar
  174. 174.
    W. Pigman and H. S. Isbell, Adv. Carbohydrate Chem., 23, 11 (1968); H. S. Isbell and W. Pigman, Adv. Carbohydrate Chem., 24, 14 (1969).Google Scholar
  175. 175.
    J. M. Los, L. B. Simpson, and K. Wiesner, J. Am. Chem. Soc., 78, 1564 (1956).CrossRefGoogle Scholar
  176. 176.
    T. M. Lowry and G. F. Smith, J. Chem. Soc., 2539 (1927).Google Scholar
  177. 177.
    J. N. Brönsted and E. A. Guggenheim, J. Am. Chem. Soc., 49, 2554 (1927).CrossRefGoogle Scholar
  178. 178.
    J. M. Los and L. B. Simpson, Rec. Tray. Chim., 76, 267 (1957).CrossRefGoogle Scholar
  179. 179.
    F. Covitz and F. H. Westheimer, J. Am. Chem. Soc., 85, 1773 (1963).CrossRefGoogle Scholar
  180. 180.
    F. H. Westheimer, J. Org. Chem., 2, 431 (1938).CrossRefGoogle Scholar
  181. 181.
    G. E. Lienhard and F. H. Anderson, J. Org. Chem., 32, 2229 (1967).CrossRefGoogle Scholar
  182. 182.
    G. F. Smith and M. C. Smith, J. Chem. Soc., 1413 (1937); J. C. Kendrew and E. A. Moelwyn-Hughes, Proc. Roy. Soc., A, 176, 352 (1940); P. Johnson and E. A. Moelwyn-Hughes, Trans. Faraday Soc., 37, 289 (1941); D. G. Hill and B. A. Thumm, J. Am. Chem. Soc., 74, 1380 (1952); G. Kilde and W. F. K. Wynne-Jones, Trans. Faraday Soc., 49, 243 (1953).Google Scholar
  183. 183.
    H. H. Huang, R. R. Robinson, and F. A. Long, J. Am. Chem. Soc., 88, 1866 (1966).CrossRefGoogle Scholar
  184. 184.
    E. Berliner, Progr. Phys. Org. Chem., 2, 253 (1964).CrossRefGoogle Scholar
  185. 185.
    For a review of hydrogen isotope effects in aromatic substitution reactions, see H. Zollinger, Adv. Phys. Org. Chem., 2, 163 (1964).CrossRefGoogle Scholar
  186. 186.
    G. A. Olah and S. J. Kuhn, J. Am. Chem. Soc., 80, 6535, 6540 (1958).CrossRefGoogle Scholar
  187. 187.
    L. Melander, Arkiv Kemi, 2, 213 (1950).Google Scholar
  188. 188.
    U. Berglund-Larsson and L. Melander, Arkiv Kemi, 6, 219 (1953): U. Berglund- Larsson, Arkiv Kemi, 10, 549 (1957).Google Scholar
  189. 189.
    H. Zollinger, Heir. Chim. Acta, 38, 1597, 1617, 1633 (1955); Diazo and Azo Chemistry, Interscience, New York, 1961: R. Ernst, O. A. Stamm, and H. Zollinger, Hely. Chim Acta, 41, 2274 (1958): C. Jermini, S. Koller, and H. Zollinger, Helr. Chim. Acta, 53, 72 (1970).Google Scholar
  190. 190.
    A. J. Kresge and Y. Chiang, J. Am. Chem. Soc., 81, 5509 (1959); 83, 2877 (1961); A. J. Kresge, S. Slae, and D. «r. Taylor, J. Am. Chem. Soc., 92, 6309 (1970).Google Scholar
  191. 191.
    J. Colapietro and F. A. Long, Chem. and Ind., 1056 (1960); B. C. Challis and F. A. Long, J. Am. Chem. Soc., 85, 2524 (1963); J. Schulze and F. A. Long, J. Am. Chem. Soc., 86, 331 (1964); R. J. Thomas and F. A. Long, J. Am. Chem. Soc., 86, 4770 (1964). References for Table 22, p. 172. (a) F. O. Rice and M. Kilpatrick, J. Am. Chem. Soc., 45, 1401 (1923); (b) H. M. Dawson, Trans. Faradati Soc., 24, 640 (1928); (c) M. Bamford and R. P. Bell, unpublished measurements; (d) H. M. Dawson and A. Key, J. Chem. Soc., 2154 (1928); (e) G. F. Smith, J. Chem. Soc., 1744 (1934); (f) O. Reitz, Z. Phys. Chem., A, 179, 119 (1937); (g) F. O. Rice and C. F. Fryling, J. Am. Chem. Soc., 47, 382 (1925); (h) R. P. Bell and K. Yates, J. Chem. Soc.. 1927 (1962).Google Scholar

Copyright information

© R. P. Bell 1973

Authors and Affiliations

  • R. P. Bell
    • 1
  1. 1.University of StirlingScotland

Personalised recommendations