Advertisement

Nitrogen NMR pp 261-317 | Cite as

Correlations of Nitrogen Coupling Constants with Molecular Structure

  • Theodore Axenrod

Abstract

In recent years, as the commercial availability of 15N-enriched compounds has grown, interest has increasingly focused on the measurement and interpretation of nitrogen spin-spin couplings as an aid in spectral analysis and structure elucidation. Although present theory is unable to predict accurate values of these couplings, a knowledge of the range of coupling constants found for different molecular systems has considerable potential for structure determination. This chapter is concerned with the correlation of nitrogen coupling constants with molecular structure. The coupling constant data presented here are largely derived from 15N-enriched compounds, but in certain cases data for 14N couplings are available. To facilitate comparisons the latter are converted to the corresponding 15N values by multiplication by |γ (15N)/γ(14N)| = 1.402. The subject of nitrogen NMR has previously been reviewed by Witanowski and Webb [1], Randall and Gillies [10], Mooney and Winson [11] and by Lichter [12].

Keywords

Spin Coupling Tautomeric Equilibrium Aniline Derivative Fermi Contact Geminal Coupling 
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.
    M. WITANOWSKI and G. A. WEBB, in Annual Review of N.M.R. Spectroscopy, Vol. 5 (E. F. Mooney, Ed.), Academic Press, London, 1972, p. 395.Google Scholar
  2. 2.
    C. M. SHEPPERD, T. SCHAEFFER, B. W. GOODWIN, and J. T. RAA, Can. J. Chem., 49, 3158 (1971).Google Scholar
  3. 3.
    J. P. KINTZINGER, J. M. LEHN, and R. L. WILLIAMS, Mol. Phys., 17, 135 (1969).Google Scholar
  4. 4.
    T. AXENROD and F. MACCHIA, unpublished results.Google Scholar
  5. 5.
    M. LILER, J. Mag. Resonance, 5, 333 (1971).Google Scholar
  6. 6.
    J. B. LAMBERT, G. BINSCH, and J. D. ROBERTS, Proc. Nat. Acad. Sci. U.S., 51, 735 (1964).Google Scholar
  7. 7.
    T. J. BATTERHAM and C. BIGUM, Org. Mag. Resonance, in press.Google Scholar
  8. 8.
    M. WITANOWSKI, J. Amer. Chem. Soc., 90, 5683 (1968).Google Scholar
  9. 9.
    E. D. BECKER, R. B. BRADLEY, and T. AXENROD, J. Mag. Resonance, 4, 136 (1971).Google Scholar
  10. 10.
    E. W. RANDALL and D. G. GILLIES, in Progress in Nuclear Magnetic Resonance Spectroscopy, Vol. 6 (J. W. Emsley, J. Feeney, and L. H. Sutcliffe, Eds.), Pergamon Press, Oxford, 1971, p. 119.Google Scholar
  11. 11.
    E. F. MOONEY and P. H. WINSON, in Annual Review of N.M.R. Spectroscopy, Vol. 2 (E. F. Mooney, Ed.), Academic Press, London, 1969, p. 125.Google Scholar
  12. 12.
    R. L. LICHTER, in Determination of Organic Structures by Physical Methods, Vol. 4 (J. J. Zuckerman and F. C. Nachod, Eds.), Academic Press, New York, London, 1972, p. 195.Google Scholar
  13. 13.
    J. W. EMSLEY, J. FEENEY, and L. H. SUTCLIFFE, in High Resolution Nuclear Magnetic Resonance Spectroscopy, Vol. 1, Pergamon Press, Oxford, 1965, pp. 103 ff.Google Scholar
  14. 14.
    W. MCFARLANE, Quart. Rev., 187 (1969).Google Scholar
  15. 15.
    G. E. MACIEL, J. W. MCIVER Jr., N. S. OSTLUND, and J. A. POPLE, J. Amer. Chem. Soc., 92, 1 (1970).Google Scholar
  16. 16.
    D. M. GRANT and W. M. LITCHMAN, J. Amer. Chem. Soc., 87, 3994 (1965).Google Scholar
  17. 17.
    T. L. BROWN and J. C. PUCKETT, J. Chem. Phys., 44, 2238 (1966).Google Scholar
  18. 18.
    G. BINSCH, J. B. LAMBERT, B. W. ROBERTS, and J. D. ROBERTS, J. Amer. Chem. Soc., 86, 5564 (1964).Google Scholar
  19. 19.
    A. J. R. BOURN and E. W. RANDALL, Mol. Phys., 8, 567 (1964).Google Scholar
  20. 20.
    J. A. POPLE and D. P. SANTRY, Mol. Phys., 8, 1 (1964).Google Scholar
  21. 21.
    Y. KATO, M. MIURA, and A. SAIKA, Mol. Phys., 13, 491 (1967).Google Scholar
  22. 22.
    H. S. GUTOWSKY, C. H. HOLM, A. SAIKA, and G. A. WILLIAMS, J. Amer. Chem. Soc., 79, 4596 (1957).Google Scholar
  23. 23.
    R. FREEMAN, K. A. MCLAUCHLAN, J. I. MUSHER, and K. G. R. PACHLER, Mod. Phys., 5, 321 (1962).Google Scholar
  24. 24.
    R. FREEMAN and W. A. ANDERSON, J. Chem. Phys., 37, 2053 (1962).Google Scholar
  25. 25.
    K. KUHLMANN and J. D. BALDESCHWEILER, J. Amer. Chem. Soc., 85, 1010 (1963).Google Scholar
  26. 26.
    R. FREEMAN and B. GESTBLOM, J. Chem. Phys., 48, 5008 (1968).Google Scholar
  27. 27.
    E. RAHKAMAA, Mol Phys., 19, 727 (1970).Google Scholar
  28. 28.
    E. RAHKAMAA, Z. Naturforsch, 24A, 2004 (1969).Google Scholar
  29. 29.
    D. GAGNAIRE, R. RAMASSEUL, and A. RASSAT, Bull Soc. Chim. Fr., 415 (1970).Google Scholar
  30. 30.
    G. A. KALABIN, V. F. BYSTROV, E. V. SHEPELEV, S. N. SHVEDOVA, O. B. LEBEDEV, and L. I. KHMEL’NITSKII, Izv. Akad. Nauk. SSSR. Ser. Khim., 2627 (1969).Google Scholar
  31. 31.
    R. J. CHUCK, D. G. GILLIES, and E. W. RANDALL, Mol. Phys., 16, 121 (1969).Google Scholar
  32. 32.
    A. J. R. BOURN, D. G. GILLIES, and E. W. RANDALL in Nuclear Magnetic Resonance in Chemistry (B. Pesce, Ed.), Academic Press Inc., New York, N.Y., 1965, p. 277.Google Scholar
  33. 33.
    L. PAOLILLO and E. D. BECKER, J. Mag. Resonance, 3, 200 (1970).Google Scholar
  34. 34.
    D. CREPAUX, J. M. LEHN, and R. R. DEAN, Mol. Phys., 16, 225 (1969).Google Scholar
  35. 35.
    A. J. R. BOURN and E. W. RANDALL, J. Mol. Spectrosc., 13, 29, (1964).Google Scholar
  36. 36.
    D. CREPAUX and J. M. LEHN, Mol Phys., 14, 547 (1968).Google Scholar
  37. 37.
    K. TORI, M. OHTSURU, K. AONO, Y. KAWAZOE, and M. OHNISHI, J. Amer. Chem. Soc., 89, 2765 (1967).Google Scholar
  38. 38.
    W. MCFARLANE, J. Chem. Soc. (A), 1660 (1967).Google Scholar
  39. 39.
    J. P. MAHER, J. Chem. Soc. (A), 1855 (1966). Google Scholar
  40. 40.
    M. OHTSURU, K. TORI, J. M. LEHN, and R. SEHER, J. Amer. Chem. Soc., 91, 1187 (1969).Google Scholar
  41. 41.
    W. MCFARLANE and R. R. DEAN, J. Chem. Soc (A), 1187 (1968).Google Scholar
  42. 42.
    W. MCFARLANE, Mol Phys., 10, 603 (1966).Google Scholar
  43. 43.
    A. H. COWLEY, J. R. SCHWEIGER, and S. L. MANATT, Chem. Commun., 1491 (1970).Google Scholar
  44. 44.
    W. MCFARLANE, J. Chem. Soc. (A), 1535 (1968).Google Scholar
  45. 45.
    R. B. JOHANNESEN, J. Chem. Phys., 48, 1414 (1968).Google Scholar
  46. 46.
    I. D. KUNTZ Jr., P. von R. SCHLEYER, and A. ALLERHAND, J. Chem. Phys., 35, 1533 (1961).Google Scholar
  47. 47.
    E. GRUNWALD, A. LOEWENSTEIN, and S. MEIBOOM, J. Chem. Phys., 27, 630 (1957).Google Scholar
  48. 48.
    A. H. LAMBERTON, I. O. SUTHERLAND, J. E. THORPE, and H. M. YUSUF, J. Chem. Soc. (B), 6 (1968).Google Scholar
  49. 49.
    P. HAMPSON and A. MATHIAS, Chem. Commun., 825 (1968).Google Scholar
  50. 50.
    A. D. BUCKINGHAM and K. A. MCLAUCHLAN, Proc. Chem. Soc., 144 (1963).Google Scholar
  51. 51.
    R. A. BERNHEIM and B. J. LAVERY, J. Amer. Chem. Soc., 88, 1279 (1967).Google Scholar
  52. 52.
    A. J. R. BOURN, D. G. GILLIES, and E. W. RANDALL, Tetrahedron, 20, 1811 (1964).Google Scholar
  53. 53.
    K. A. MCLAUCHLAN and T. SCHAEFER, Can. J. Chem., 44, 321 (1966).Google Scholar
  54. 54.
    E. SACKMANN and H. DREESKAMP, Spectrochim. Acta, 21, 2005 (1965).Google Scholar
  55. 55.
    H. HOGEVEEN, Rec. Trav. Chim., 86, 1288 (1967).Google Scholar
  56. 56.
    L. PAOLILLO and E. D. BECKER, J. Mag. Resonance, 2, 168 (1970).Google Scholar
  57. 57.
    R. A. BERNHEIM and H. BATIZ-HERNANDEZ, J. Chem. Phys., 40, 3446 (1964).Google Scholar
  58. 58.
    M. ALEI Jr., A. E. FLORIN, W. LITCHMAN, and J. F. O’BRIEN, J. Phys. Chem., 75, 932 (1971).Google Scholar
  59. 59.
    W. LITCHMAN, M. ALEI Jr., and A. E. FLORIN, J. Chem. Phys., 50, 1897 (1969).Google Scholar
  60. 60.
    R. A. OGG and J. D. RAY, J. Chem. Phys., 26, 1515 (1957).Google Scholar
  61. 61.
    M. ALEI Jr., A. E. FLORIN, and W. M. LITCHMAN, J. Phys. Chem., 75, 1758 (1971).Google Scholar
  62. 62.
    J. D. BALDESCHWEILER, J. Chem. Phys., 36, 152 (1962).Google Scholar
  63. 63.
    C. S. SPRINGER and D. W. MEEK, J. Phys. Chem., 70, 481 (1966).Google Scholar
  64. 64.
    K. L. HENOLD, Chem. Commun., 1340 (1970).Google Scholar
  65. 65.
    D. W. MEEK and C. S. SPRINGER, Inorg. Chem., 5, 445 (1966).Google Scholar
  66. 66.
    Tables of Interatomic Distances and Configurations in Molecules and Ions, The Chemical Society, London, 1958.Google Scholar
  67. 67.
    M. WITANOWSKI, L. STEFANIAK, H. JANUSZEWSKI, and G. A. WEBB, Tetrahedron, 27, 3129 (1971).Google Scholar
  68. 68.
    D. M. BROUWER and J. A. van DOORN, Tetrahedron Letters, 3339 (1971).Google Scholar
  69. 69.
    E. RAHKAMAA, Z. Naturforsch., 26A, 1187 (1971).Google Scholar
  70. 70.
    E. W. RANDALL and J. J. ZUCKERMAN, Chem. Commun., 732 (1966).Google Scholar
  71. 71.
    M. OHTSURU and K. TORI, Chem. Commun., 750 (1966).Google Scholar
  72. 72.
    L. K. DYALL, Aust. J. Chem., 17, 419 (1963).Google Scholar
  73. 73.
    Y. YONEMOTO, W. F. REYNOLDS, H. M. HUTTON, and T. SCHAEFFER, Can. J. Chem., 43, 2688 (1965).Google Scholar
  74. 74.
    B. M. LYNCH, B. C. MACDONALD, and J. K. G. WEBB, Tetrahedron, 24, 3595 (1968).Google Scholar
  75. 75.
    B. M. LYNCH, Tetrahedron Letts., 1357 (1969).Google Scholar
  76. 76.
    T. AXENROD, P. S. PREGOSIN, M. J. WIEDER, and G. W. A. MILNE, J. Amer. Chem. Soc., 91, 3681 (1969).Google Scholar
  77. 77.
    M. R. BRAMWELL and E. W. RANDALL, Chem. Commun., 250 (1969).Google Scholar
  78. 78.
    T. AXENROD, P. S. PREGOSIN, M. J. WIEDER, E. D. BECKER, R. B. BRADLEY, and G. W. A. MILNE, J. Amer. Chem. Soc., 93, 6536 (1971).Google Scholar
  79. 79.
    V. V. NEGREBETSKII, A. V. KESSENIKH, S. S. NOVIKOV, L. I. KHMELINITII, A. S. PRIKHODIKO, and O. V. LEBEDEV, Izv. Akad. Nauk. SSSR, Ser. Khim., 2163 (1971).Google Scholar
  80. 80.
    T. AXENROD, M. J. WIEDER, G. BERTI, and P. L. BARILI, J. Amer. Chem. Soc., 92, 6066 (1970).Google Scholar
  81. 81.
    T. AXENROD and M. J. WIEDER, unpublished results.Google Scholar
  82. 82.
    G. FRAENKEL, Y. ASAHI, H. BATIZ-HERNANDEZ, and R. A. BERNHEIM, J. Chem. Phys., 44, 4647 (1966).Google Scholar
  83. 83.
    L. ERNST and A. MANNSCHRECK, Tetrahedron Letts., 3023 (1971).Google Scholar
  84. 84.
    C. BEAUTE, Z. W. WOLKOWSKI, and N. THOAI, Tetrahedron Letts., 817 (1971).Google Scholar
  85. 85.
    J. K. M. SANDERS and D. H. WILLIAMS, J. Amer. Chem. Soc., 93, 641 (1971).Google Scholar
  86. 86.
    T. AXENROD and M. J. WIEDER, J. Amer. Chem. Soc., 93, 3541 (1971).Google Scholar
  87. 87.
    I. D. RAE, Chem. Commun., 519 (1966).Google Scholar
  88. 88.
    I. D. RAE, Aust. J. Chem., 20, 1173 (1967).Google Scholar
  89. 89.
    V. BEKAREK, J. KAVALEK, J. SOCHA, and S. ANDRYSEK, Chem. Commun., 630 (1968).Google Scholar
  90. 90.
    T. AXENROD, G. BERTI, and G. BELLUCCI, unpublished results.Google Scholar
  91. 91.
    T. AXENROD and P. S. PREGOSIN, unpublished results.Google Scholar
  92. 92.
    A. K. BOSE and I. KUGAJEVSKY, Tetrahedron, 23, 1489 (1967).Google Scholar
  93. 93.
    G. J. LESTINA, G. P. HAPP, D. P. MAIER, and T. H. REGAN, J. Org. Chem., 33, 3336 (1968).Google Scholar
  94. 94.
    R. R. SHOUP, H. T. MILES, and E. D. BECKER, Biochem. Biophys. Res. Commun., 23, 194 (1966).Google Scholar
  95. 95.
    R. D. GREEN, Can. J. Chem., 47, 2407 (1969).Google Scholar
  96. 96.
    H. KAMEI, Bull. Chem. Soc., Japan, 38, 1212 (1965).Google Scholar
  97. 97.
    J. B. LAMBERT, B. W. ROBERTS, G. BINSCH, and J. D. ROBERTS, in Nuclear Magnetic Resonance in Chemistry (B. Pesce, Ed.), Academic Press Inc., New York, N.Y., 1965, p. 269.Google Scholar
  98. 98.
    J. B. LAMBERT, W. L. OLIVER, and J. D. ROBERTS, J. Amer. Chem. Soc., 87, 5085 (1965).Google Scholar
  99. 99.
    J. NELSON, R. SPRATT, and S. M. NELSON, J. Chem. Soc (A), 583 (1970).Google Scholar
  100. 100.
    K. M. MACKAY and S. R. STOBART, Spectrochim. Acta, 27A, 923 (1971).Google Scholar
  101. 101.
    T. AXENROD, G. BERTI, and P. L. BARILI, unpublished results.Google Scholar
  102. 102.
    R. WASYLISHEN and T. SCHAEFFER, Can. J. Chem., 49, 3627 (1971).Google Scholar
  103. 103.
    G. A. OLAH and T. E. KIOVSKY, J. Amer. Chem. Soc., 90, 4666 (1968).Google Scholar
  104. 104.
    T. AXENROD and F. MACCHIA, unpublished results.Google Scholar
  105. 105.
    K. TABEI and E. SAITOU, Bull. Chem. Soc Japan, 42, 1440 (1969) and references therein.Google Scholar
  106. 106.
    H. B. BÜRGI and J. D. DUNITZ, Helv. Chim. Acta, 53, 1747 (1970)Google Scholar
  107. 106a.
    H. B. BÜRGI and J. D. DUNITZ, Helv. Chim. Acta, 54, 1255 (1971).Google Scholar
  108. 107.
    V. BEKAREK, J. KLICNAR, F. KRISTEK, and M. VECERA, Collect. Czech. Chem. Commun., 33, 994 (1968).Google Scholar
  109. 108.
    M. WITANOWSKI, Tetrahedron, 23, 4299 (1967).Google Scholar
  110. 109.
    P. S. PREGOSIN, E. W. RANDALL, and A. I. WHITE, J. Chem. Soc (B), 513 (1972).Google Scholar
  111. 110.
    C. D. COOK and S. S. DANYLUK, Tetrahedron, 19, 177 (1963).Google Scholar
  112. 111.
    L. LUNAZZI, D. MACCIANTELLI, and F. TADDEI, Mol. Phys., 19, 137 (1970).Google Scholar
  113. 112.
    B. SUNNERS, L. H. PIETTE, and W. G. SCHNEIDER, Can. J. Chem. 38, 681 (1960).Google Scholar
  114. 113.
    M. T. ROGERS and L. A. LAPLANCHE, J. Phys. Chem., 69, 3648 (1965).Google Scholar
  115. 114.
    W. WALTER, H. P. KUBERSKY, E. SCHAUMANN, and K. J. REUBKE, Ann. Chem., 719, 210 (1968).Google Scholar
  116. 115.
    E. W. RANDâLL and J. J. ZUCKERMAN, J. Amer. Chem. Soc., 90, 3167 (1968).Google Scholar
  117. 116.
    A. H. COWLEY and J. R. SCHWEIGER, Chem. Commun., 1492 (1970).Google Scholar
  118. 117.
    E. BULLOCK, D. G. TUCK, and E. J. WOODHOUSE, J. Chem. Phys., 38, 2318 (1963).Google Scholar
  119. 118.
    R. L. LICHTER and J. D. ROBERTS, J. Amer. Chem. Soc., 93, 5218 (1970).Google Scholar
  120. 119.
    I. MORISHIMA, A. MIZUNO, T. YONEZAWA, and K. GOTO, Chem. Commun., 1321 (1970).Google Scholar
  121. 120.
    G. E. MACIEL, J. W. MCIVER Jr., N. S. OSTLUND, and J. A. POPLE, J. Amer. Chem. Soc., 92, 11 (1970).Google Scholar
  122. 121.
    P. S. PREGOSIN, E. W. RANDALL, and A. I. WHITE, J. Chem. Soc., Perkin Trans II, 1 (1972).Google Scholar
  123. 122.
    W. H. HALE Jr. and S. M. WILLIAMSON, Inorg. Chem., 4, 1343 (1965).Google Scholar
  124. 123.
    J. M. SCHREEVE, L. C. DUNCAN, and G. H. CADY, Inorg. Chem., 4, 1516 (1965).Google Scholar
  125. 124.
    W. B. FOX, J. S. MACKENZIE, E. R. MCCARTHY, J. R. HOLMES, R. F. STAHL, and R. JUURICK, Inorg. Chem., 7, 2064 (1968).Google Scholar
  126. 125.
    J. H. NOGGLE, J. D. BALDESCHWEILER, and C. B. COLBURN, J. Chem. Phys., 37, 182 (1962).Google Scholar
  127. 126.
    W. B. FOX, G. FRANZ, and L. R. ANDERSON, Inorg. Chem. 7, 383 (1968).Google Scholar
  128. 127.
    W. E. TOLBERG, R. T. REWICK, R. S. STRINGHAM, and M. E. HILL, Inorg. Chem., 6, 1156 (1967).Google Scholar
  129. 128.
    K. O. CHRISTIE, J. P. GUERTIN, A. E. PAVLATH, and W. SAWODNY, Inorg. Chem., 6, 533 (1967).Google Scholar
  130. 129.
    V. GRAKAUSKAS and K. BAUN, J. Org. Chem., 33, 3080 (1968).Google Scholar
  131. 130.
    A. V. CUNLIFFE and R. K. HARRIS, Mol. Phys., 15, 413 (1968).Google Scholar
  132. 131.
    R. K. HARRIS and N. C. PYPER, R. E. RICHARDS, and G. W. SCHULZ, Mol. Phys., 19, 145 (1970).Google Scholar
  133. 132.
    C. REICHARDT, personal communication.Google Scholar
  134. 133.
    D. MOY and A. R. YOUNG, J. Amer. Chem. Soc., 87, 1889 (1965).Google Scholar
  135. 134.
    For a review of restricted rotation in amides, see T. H. SIDDALL and W. E. STEWART, in Progress in Nuclear Magnetic Resonance Spectroscopy, Vol. 5 (J. W. Emsley, J. Feeney, and L. H. Sutcliffe, Eds.) Pergamon Press, Oxford, 1969, p. 33.Google Scholar
  136. 135.
    J. LADELL and B. POST, Acta Cryst., 7, 559 (1954).Google Scholar
  137. 136.
    C. C. COSTAIN and J. M. DOWLING, J. Chem. Phys., 32, 158 (1960).Google Scholar
  138. 137.
    E. W. RANDALL, J. J. ELLNER, and J. J. ZUCKERMAN, J. Amer. Chem. Soc., 88, 622 (1966).Google Scholar
  139. 138.
    C. GLIDEWELL, D. W. H. RANKIN, A. G. ROBIETTE, and G. M. SHELDRICK, J. Mol Struct., 4, 215 (1969).Google Scholar
  140. 139.
    T. AXENROD and E. D. BECKER, unpublished results.Google Scholar
  141. 140.
    N. LOGAN and W. L. JOLLY, Inorg. Chem., 4, 1508 (1965).Google Scholar
  142. 141.
    R. FIELDS, J. LEE, and D. J. MOWTHORPE, Trans. Faraday Soc., 65, 2278 (1969).Google Scholar
  143. 142.
    P. FRIEDMAN, Inorg. Chem., 8, 692 (1969)Google Scholar
  144. 143.
    G. A. GRAY, Ph.D. Dissertation, University of Calif., Davis, 1967.Google Scholar
  145. 144.
    G. LECOUSTUMER and Y. MOLLIER, Bull. Soc. Chim. Fr., 2244 (1970).Google Scholar
  146. 145.
    F. G. RIDDELL and J. M. LEHN, J. Chem. Soc. (B), 1224 (1968).Google Scholar
  147. 146.
    A. A. BOTHNER-BY and R. H. COX, J. Phys. Chem., 73, 1830 (1969).Google Scholar
  148. 147.
    N. BARTLETT, J. PASSMORE, and E. J. WELLS, Chem. Commun., 213 (1966).Google Scholar
  149. 148.
    A. M. QURESHI, J. A. RIPMEESTER, and F. AUBKE, Can. J. Chem., 47, 4247 (1969).Google Scholar
  150. 149.
    R. A. OGG and J. D. RAY, J. Chem. Phys., 25, 797 (1956).Google Scholar
  151. 150.
    E. L. MUETTERTIES and W. D. PHILLIPS, J. Amer. Chem. Soc., 81, 1084 (1959).Google Scholar
  152. 151.
    M. OHTSURU and K. TORI, Tetrahedron Letts., 4043 (1970).Google Scholar
  153. 152.
    D. M. JERINA, D. R. BOYD, L. PAOLILLO, and E. D. BECKER, Tetrahedron Letts, 1483 (1970).Google Scholar
  154. 153.
    H. PAULSEN and W. GREVE, Chem. Ber., 103, 486 (1970).Google Scholar
  155. 154.
    J. P. KINTZINGER and J. M. LEHN, Chem. Commun., 660 (1967).Google Scholar
  156. 155.
    J. P. KINTZINGER and J. M. LEHN, Mol. Phys., 14, 133 (1968).Google Scholar
  157. 156.
    J. M. LEHN and R. SEHER, Chem. Commun., 847 (1966).Google Scholar
  158. 157.
    V. I. ERASHKO, S. A. SHEVELEV, A. A. FAINZIL’BERG, M.YA. MäGI, and E. T. LIPPMAA, Izv. Akad, Nauk. SSSR. Ser. Khim., 958 (1970).Google Scholar
  159. 158.
    J. C. WOODBREY and M. T. ROGERS, J. Amer. Chem. Soc., 84, 13 (1962).Google Scholar
  160. 159.
    D. J. BERTELLI and J. T. GERIG, Tetrahedron Letts., 2481 (1967).Google Scholar
  161. 160.
    T. GOTO, M. ISOBE, M. OHTSURU, and K. TORI, Tetrahedron Letts., 1511 (1968).Google Scholar
  162. 161.
    R. K. BOHN and S. H. BAUER, Inorg. Chem., 6, 309 (1967).Google Scholar
  163. 162.
    G. BINSCH and J. D. ROBERTS, J. Phys. Chem., 72, 4310 (1968).Google Scholar
  164. 163.
    T. AXENROD, Spectrosc Letts., 3, 263 (1970).Google Scholar
  165. 164.
    P. G. GASSMAN and D. C. HECKERT, J. Org. Chem., 30, 2859 (1965).Google Scholar
  166. 165.
    E. W. RANDALL and D. SHAW, Spectrochim. Acta, 23A, 1235 (1967).Google Scholar
  167. 166.
    J. M. LEHN and M. FRANCK-NEUMANN, J. Chem. Phys., 43, 1421 (1965).Google Scholar
  168. 167.
    J. F. BIELLMANN and H. CALLOT, Bull. Soc. Chim. Fr., 397 (1967).Google Scholar
  169. 168.
    Y. TERUI, K. AONO, and K. TORI, J. Amer. Chem. Soc., 90, 1069 (1968).Google Scholar
  170. 169.
    R. L LICHTER and J. D. ROBERTS, J. Org. Chem., 35, 2806 (1970).Google Scholar
  171. 170.
    T. YONEZAWA, I. MORISHIMA, K. FUKUTA, and Y. OHMORI, J. Mol. Spectrosc., 31, 341 (1969).Google Scholar
  172. 171.
    H. KAMEI, Bull Chem. Soc. Japan, 41, 2269 (1968).Google Scholar
  173. 172.
    R. ETTINGER and C. B. COLBURN, Inorg. Chem., 2, 1311 (1963).Google Scholar
  174. 173.
    G. O. DUDEK and E. P. DUDEK, J. Amer. Chem. Soc., 86, 4283 (1964).Google Scholar
  175. 174.
    G. O. DUDEK and E. P. DUDEK, Tetrahedron, 23, 3245 (1967).Google Scholar
  176. 175.
    G. O. DUDEK and E. P. DUDEK, J. Amer. Chem. Soc., 88, 2407 (1966).Google Scholar
  177. 176.
    E. D. BECKER, H. T. MILES, and R. B. BRADLEY, J. Amer. Chem. Soc., 87, 5575 (1965).Google Scholar
  178. 177.
    B. W. ROBERTS, J. B. LAMBERT, and J. D. ROBERTS, J. Amer. Chem. Soc., 87, 5439 (1965).Google Scholar
  179. 178.
    H. T. MILES, R. B. BRADLEY, and E. D. BECKER, Science, 142, 1569 (1963).Google Scholar
  180. 179.
    Y. KAWAZOE, M. ARAKI, S. SAWAKI, and M. OHNISHI, Chem. Pharm. Bull. (Tokyo), 18, 381 (1970).Google Scholar
  181. 180.
    Y. KAWAZOE, M. OHNISHI, and N. KATAOKA, Chem. Pharm. Bull. (Tokyo), 13, 396 (1965).Google Scholar
  182. 181.
    T. AXENROD, P. S. PREGOSIN, and G. W. A. MILNE, Chem. Commun., 702 (1968).Google Scholar
  183. 182.
    T. AXENROD, P. S. PREGOSIN, and G. W. A. MILNE, Tetrahedron Letts., 5293 (1968).Google Scholar
  184. 183.
    T. AXENROD, M. J. WIEDER, and G. W. A. MILNE, Tetrahedron Letts., 401 (1969).Google Scholar
  185. 184.
    T. AXENROD, M. J. WIEDER, and G. W. A. MILNE, Tetrahedron Letts., 1397 (1969).Google Scholar
  186. 185.
    J. N. MURRELL, in Progress in Nuclear Magnetic Resonance Spectroscopy, Vol. 6 (J. W. Emsley, J. Feeney, and L. H. Sutcliffe, Eds.), Pergamon Press, Oxford, 1971, p. 7.Google Scholar
  187. 186.
    R. A. COBURN and G. O. DUDEK, J. Phys. Chem., 72, 1177 (1968).Google Scholar
  188. 187.
    S. M. BLOOM and G. O. DUDEK, J. Org. Chem., 36, 235 (1971).Google Scholar
  189. 188.
    V. BEKAREK, K. ROTHSCHEIN, P. VETESNIK, and M. VECERA, Tetrahedron Letts., 3711 (1968).Google Scholar
  190. 189.
    V. BEKAREK, J. DOBAS, J. SOCHA, P. VETESNIK, and M. VECERA, Collect. Czech. Chem. Commun., 35, 1406 (1970).Google Scholar
  191. 190.
    A. H. BERRIE, P. HAMPSON, S. W. LONGWORTH, and A. MATHIAS, J. Chem. Soc. (B), 1308 (1968).Google Scholar
  192. 191.
    G. J. LESTINA and T. H. REGAN, J. Org. Chem., 34, 1686 (1969).Google Scholar
  193. 192.
    C. REICHARDT and W. GRAHN, Tetrahedron, 27, 3745 (1971).Google Scholar
  194. 193.
    C. REICHARDT and W. GRAHN, Chem. Ber., 103, 1065 (1970).Google Scholar
  195. 194.
    V. S. BOGDANOV, M. A. KALIK, YA. L. DANYUSHEVSKII, and YA. L. GOLDFARB, Izv. Akad. Nauk. SSSR. Ser. Khim., 2783 (1967).Google Scholar
  196. 195.
    M-L. BLANCHARD, H. STRZELECKA, G. J. MARTIN, M. SIMALTY, and R. FUGNITTO, Bull. Soc. Chim. Fr., 2677 (1967).Google Scholar
  197. 196.
    G. KLOSE and E. UHLEMANN, Tetrahedron, 22, 1373 (1966).Google Scholar
  198. 197.
    P. HAMPSON and A. MATHIAS, Chem. Commun., 371 (1967).Google Scholar
  199. 198.
    L. MESTER, A. STEPHEN, and J. PARELLO, Tetrahedron Letts., 4119 (1968).Google Scholar
  200. 199.
    P. B. FISCHER, B. L. KAUL, and H. ZOLLINGER, Helv. Chim. Acta, 51, 1449 (1968).Google Scholar
  201. 200.
    L. MESTER and G. VASS, Tetrahedron Letts., 3847 (1969).Google Scholar
  202. 201.
    L. MESTER, G. VASS, A. STEPHEN and J. PARELLO, Tetrahedron Letts., 4053 (1968).Google Scholar
  203. 202.
    M. LILER, Chem. Commun., 115 (1971).Google Scholar
  204. 203.
    S. J. KUHN and J. S. MCINTYRE, Can. J. Chem., 44, 105 (1966).Google Scholar
  205. 204.
    T. BIRCHALL and R. J. GILLESPIE, Can. J. Chem., 41, 2642 (1963).Google Scholar
  206. 205.
    G. A. OLAH and A. M. WHITE, J. Amer. Chem. Soc., 90, 6087 (1968).Google Scholar
  207. 206.
    G. A. OLAH and R. H. SCHLOSBERG, J. Amer. Chem. Soc., 90, 6464 (1968).Google Scholar
  208. 207.
    R. A. OGG Jr. and J. D. RAY, J. Chem. Phys., 26, 1339, 1340 (1957).Google Scholar
  209. 208.
    G. O. DUDEK and E. P. DUDEK, Chem. Commun., 465 (1965).Google Scholar
  210. 209.
    R. R. FRASER and K. E. HAGUE, Can. J. Chem., 46, 2855 (1968).Google Scholar
  211. 210.
    R. L. LICHTER and J. D. ROBERTS, Spectrochim. Acta, 26A, 1813 (1970).Google Scholar
  212. 211.
    C. A. SWENSON and L. KOOB, J. Phys. Chem., 74, 3376 (1970).Google Scholar
  213. 212.
    B. W. ROBERTS, J. B. LAMBERT, and J. D. ROBERTS, J. Amer. Chem. Soc., 87, 5439 (1965).Google Scholar
  214. 213.
    J. A. HAPPE and H. A. MORALES, J. Amer. Chem. Soc., 88, 2077 (1966).Google Scholar
  215. 214.
    B. COXON, Carbohyd. Res., 11, 153 (1969).Google Scholar
  216. 215.
    M. L. FILLEUX-BLANCHARD, J. FIEUX, and J. C. HALLE, Chem. Commun., 851 (1971).Google Scholar
  217. 216.
    V. M. S. GIL and S. J. S. FORMOSINHO-SIMOES, Mol. Phys., 25, 639 (1968).Google Scholar
  218. 217.
    B. COXON and L. F. JOHNSON, Carbohyd. Res., 20, 105 (1971).Google Scholar
  219. 218.
    G. DUDEK and E. P. DUDEK, J. Chem. Soc. (B), 1356 (1971).Google Scholar
  220. 219.
    R. R. SHOUP, E. D. BECKER, and H. T. MILES, Biochem. Biophys. Res. Commun., 43, 1350 (1971).Google Scholar
  221. 220.
    A. K. BOSE and I. KUGAJEVSKY, J. Amer. Chem. Soc., 88, 2325 (1966).Google Scholar
  222. 221.
    T. DRAKENBERG and S. FORSEN, J. Phys. Chem., 74, 1 (1970).Google Scholar
  223. 222.
    J. M. INSOLE and E. S. LEWIS, J. Amer. Chem. Soc., 85, 122 (1963)Google Scholar
  224. 222a.
    J. M. INSOLE and E. S. LEWIS, J. Amer. Chem. Soc., 86, 32, 34 (1964).Google Scholar
  225. 223.
    E. S. LEWIS and P. G. KOTCHER, Tetrahedron, 25, 4873 (1969).Google Scholar
  226. 224.
    V. V. NEGREBETSKII, V. S. BOGDANOV, and A. V. KESSENIKH, Zh. Struct. Khim., 12, (4) 716 (1971).Google Scholar
  227. 225.
    E. D. BECKER and R. B. BRADLEY, personal communication.Google Scholar
  228. 226.
    W. B. JENNINGS, D. R. BOYD, E. D. BECKER, R. B. BRADLEY, and D. M. JERINA, personal communication.Google Scholar

Copyright information

© Plenum Publishing Company Ltd 1973

Authors and Affiliations

  • Theodore Axenrod
    • 1
  1. 1.Department of Chemistry, The City College of the CityUniversity of New YorkNew YorkUSA

Personalised recommendations