Skip to main content
SpringerLink
Log in

The composition, structure and hydrogen bonding of the β-diketones

  • Conference paper
  • First Online:
Complex Chemistry

Part of the book series: Structure and Bonding ((STRUCTURE,volume 57))

Abstract

Proton transfer and hydrogen bonding are two aspects of the chemistry of hydrogen that respectively govern the behaviour and structure of many molecules, both simple and complex, from water to DNA. The β-dicarbonyls exhibit both of these features, and in ways which have singled them out for detailed study for many years. They provide the best known examples of keto ⇆ enol tautomerism, with the advantage of slow proton transfer and high concentrations of the enol tautomers in most cases. These enols are stabilized by intramolecular OHO hydrogen bonds which at various times have been thought of as being centred, linear hydrogen bonds that are somehow incorporated into the delocalised π system to give “aromatic” systems. Research involving structural, spectroscopic and computational techniques has deepened our understanding of these compounds and changed our picture of them. The hydrogen bonding is surprisingly strong, surprising since it is neither centred, nor linear, nor involved in the ring’s delocalized bonding, although it is certainly coupled to it. This review deals with controversies that have surrounded the β-dicarbonyls and discusses the current view that the enol tautomers are a double-minimum potential well with a low energy barrier. The review ends with a brief look at the β-thioxoketones, which provide an analogous system based on a heteronuclear SHO hydrogen bond in the enol or enethiol tautomer.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Abbreviations

AA:

acetylacetone; 2,4-pentanedione; MeCOCH2COMe

BA:

benzoylacetone; PhCOCH2COMe

αClAA:

α-chloroacetylacetone; 3-choro-2,4-pentanedione; MeCOCH(Cl)COMe

DBM:

dibenzoylmethane; PhCOCH2COPh

DMAA:

dimethylacetylacetone; 3,3-dimethyl-2,4-pentanedione; MeCOCMe2COMe

2H2AA:

deuteriated acetylacetone; MeCOCD2-COMe

HFAA:

hexafluoroacetylacetone; CF3COCH2-COCF3

IR:

infrared

MAA:

methylacetylacetone; 3-methyl-2,4-pentanedione; MeCOCH(Me)COMe

MDA:

malondialdehyde; propanedial; HCOCH2COH; the end form of this is sometimes referred to as β-hydroxyacrolein or 3-hydroxy-2-propenal, HCOCH=C(OH)H.

NMR:

nuclear magnetic resonance

R:

Raman

TAA:

thioacetylacetone; MeCSCH2COMe

TAE:

tetraacetylethane; CH(COMe)2CH-(COMe)2

TFAA:

trifluoroacetylacetone; CF3COCH2-COMe

UV:

ultraviolet

IX. References

  1. For instance, Meyer, K.: Ber. dt. Chem. Ges. 44, 2718 (1911); ibid. 45, 2843 (1912)

    Article  Google Scholar 

  2. Calvin, M., Wilson, K. W.: J. Am. Chem. Soc. 67, 2003 (1945)

    Article  CAS  Google Scholar 

  3. Holm, R. H., Cotton, F. A.: ibid. 80, 5658 (1958)

    Article  CAS  Google Scholar 

  4. Williams, D. E., Dumke, W. L., Rundle, R. E.: Acta Cryst. 15, 627 (1962)

    Article  CAS  Google Scholar 

  5. Noy, R. S., Grindin, V. A., Ershov, B. A., Kol'tsov, A. I., Zubko, V. A.: Org. Mag. Res. 7, 109 (1975)

    Article  Google Scholar 

  6. Bothner-By, A. A., Harris, R. K.: J. Org. Chem. 30, 254 (1965)

    Article  CAS  Google Scholar 

  7. George, W. O., Mansell, V. G.: J. Chem. B 132 (1968)

    Google Scholar 

  8. Yoffe, S. T., Petrovsky, P. V., Goryunov, Ye. I., Yershova, T. V., Kabachnik, M. I.: Tetrahedron 28, 2783 (1972)

    Article  Google Scholar 

  9. Veierov, D., Bercovici, T., Fischer, E., Mazur, Y., Yoger, A.: J. Am. Chem. Soc. 99, 2723 (1977)

    Article  CAS  Google Scholar 

  10. Kol'tsov, A. I., Kheifets, G. M.: Russ. Chem. Revs. 40, 773 (1971)

    Article  Google Scholar 

  11. Strohmeier, W., Hühne, I.: Z. Naturforsch. 7 b, 184 (1952)

    Google Scholar 

  12. Spencer, J. N., Holmboe, E. S., Kirschenbaum, M. R., Firth, D. W., Pinto, P. B.: Can. J. Chem. 60, 1178 (1982)

    Article  CAS  Google Scholar 

  13. Allen, G., Dwek, R. A.: J. Chem. Soc. B 161 (1966)

    Google Scholar 

  14. Rogers, M. T., Burdett, J. L.: Can. J. Chem. 43, 1516 (1965)

    Article  CAS  Google Scholar 

  15. Reeves, L. W.: ibid. 35, 1351 (1957)

    Article  CAS  Google Scholar 

  16. Kol'tsov, A. I., Golubev, N. S., Milevskaya, I. S.: J. Gen. Chem. USSR 50, 2025 (1980); transl. Zh. Obshch. Khim. 50, 2504 (1980)

    Google Scholar 

  17. Kondo, G., Takemoto, T., Ikenone, T.: J. Chem. Soc. Japan, Ind. Chem. Sect. 68, 1404 (1968)

    Google Scholar 

  18. Kato, M., Watarai, H., Suzuki, N.: Can. J. Chem. 55, 1473 (1977)

    Article  CAS  Google Scholar 

  19. Reichardt, C.: Angew. Chem. Int. Edn. Engl. 1, 29 (1965)

    Google Scholar 

  20. Gutman, V.: ibid. 9, 843 (1970)

    Article  Google Scholar 

  21. Thompson, D. W., Allred, A. L.: J. Phys. Chem. 75, 433 (1971)

    Article  Google Scholar 

  22. Rogers, M. T., Burdett, J. L.: ibid. 70, 939 (1966)

    Article  Google Scholar 

  23. Kol'tsov, A. I., Ershov, B. A.: J. Org. Chem. USSR 11, 440 (1975); transl. Zh. Org. Khim. 11, 450 (1975)

    Google Scholar 

  24. Clarke, J. H.: J. Chem. Soc. Perkin I, 1744 (1977)

    Google Scholar 

  25. Clarke, J. H.: J. Chem. Soc. Perkin II, 1326 (1978)

    Google Scholar 

  26. Clarke, J. M., Miller, J. M.: J. Chem. Soc. Perkin I, 2063 (1977)

    Article  Google Scholar 

  27. Leipert, T. K.: Org. Mag. Res. 9, 157 (1977)

    Article  CAS  Google Scholar 

  28. Raban, M., Yamamoto, G.: J. Org. Chem. 42, 2549 (1977)

    Article  CAS  Google Scholar 

  29. Emsley, J., Kuroda, R., Parker, R. J.: unpublished results

    Google Scholar 

  30. Burdett, J. L., Rogers, M. T.: J. Am. Chem. Soc. 86, 2105 (1964)

    Article  CAS  Google Scholar 

  31. Mollin, Yu. N., Ioffe, S. T., Zaev, E. E., Solov'eva, E. K., Kuchneva, E. E., Voevodskii, V. V., Kabachnik, M. I.: Izv. Akad. Nauk SSSR Ser. Khim. 1556 (1965)

    Google Scholar 

  32. Yoffe, S. T., Fedin, E. I., Petrovskii, M. I., Kabachnik, M. I.: Tet. Lett. 2661 (1966)

    Google Scholar 

  33. Yoshida, Z., Ogoshi, H., Tokumitsu, T.: Tetrahedron 26, 5691 (1970)

    Article  CAS  Google Scholar 

  34. Wirzchowski, K. L., Shugar, D., Katritski, A. R.: J. Am. Chem. Soc. 85, 827 (1963)

    Article  Google Scholar 

  35. Forsen, S., Nilsson, M.: Acta Chem. Scand. 14, 1333 (1960)

    CAS  Google Scholar 

  36. Houk, K. N., Davis, L. P., Newkomo, G. R., Duke, R. E. Jr., Nauman, R. V.: J. Am. Chem. Soc. 95, 8365 (1973)

    Google Scholar 

  37. Dahlberg, D. B., Long, F. A.: ibid. 95, 3825 (1973)

    Article  CAS  Google Scholar 

  38. Sardella, D. J., Heinert, D. H., Shapiro, B. L.: J. Org. Chem. 34, 2817 (1969)

    Article  CAS  Google Scholar 

  39. Gindin, E. A., Emelina, E. E., Ershov, B. A., Kloze, G., Kol'tsov, A. I., Shapet'ko, N. N.: Zh. Org. Khim. 5, 1890 (1969)

    CAS  Google Scholar 

  40. Nonhebel, D. C.: Tetrahedron 24, 1869 (1968)

    Article  CAS  Google Scholar 

  41. Lintvedt, R. L., Holtzclaw, H. F. Jr.: Inorg. Chem. 5, 239 (1966)

    Article  CAS  Google Scholar 

  42. Lintvedt, R. L., Holtzclaw, H. F. Jr.: J. Am. Chem. Soc. 88, 2713 (1966)

    Article  CAS  Google Scholar 

  43. Bell, R. P.: The Proton in Chemistry, 2 edn., London, Chapman & Hall 1973

    Google Scholar 

  44. Long, F. A., Watson, D.: J. Chem. Soc. 2019 (1958)

    Google Scholar 

  45. Riley, T., Long, F. A.: J. Am. Chem. Soc. 84, 522 (1962)

    Article  Google Scholar 

  46. Brown, R. S., Tse, A., Nakashima, T., Haddon, R. C.: ibid. 101, 3157 (1979)

    Article  CAS  Google Scholar 

  47. Robinson, M. J. T., Rosen, K. M., Workman, J. D. B.: Tetrahedron 33, 1655 (1977)

    Article  CAS  Google Scholar 

  48. Emsley, J.: Chem. Soc. Revs. 9, 91 (1980)

    Article  CAS  Google Scholar 

  49. Shapet'ko, N. N., Kessenikh, A. V., Skoldinov, A. P., Protopopova, T. K.: Teor. Eksper. Khim. 2, 757 (1966)

    Google Scholar 

  50. Garbisch, E. W.: J. Am. Chem. Soc. 85, 1696 (1963)

    Article  CAS  Google Scholar 

  51. Forsen, S., Nilsson, M.: Arkiv Kemi 19, 41 (1963); ibid. 20, 41 (1963)

    Google Scholar 

  52. Shapet'ko, N. N.: Org. Mag. Res. 5, 215 (1973)

    Article  Google Scholar 

  53. Gindin, V. A., Chipum, I. A., Ershov, B. E., Kol'tsov, A. I.: ibid. 4, 63 (1972)

    Article  CAS  Google Scholar 

  54. Poplett, I. J. F., Sabir, M., Smith, J. A. S.: J. Chem. Soc. Faraday Trans 2 77, 1651 (1981)

    Article  CAS  Google Scholar 

  55. Lowe, J. U., Fergusson, L. N.: J. Org. Chem. 30, 3000 (1965)

    Article  CAS  Google Scholar 

  56. Shapet'ko, N. N., Radushnova, I. L., Bogachev, Yu. S., Berestova, S. S., Potapov, V. M., Kiryuschkina, G. V., Talebarovskaya, I. K.: Org. Mag. Res. 7, 540 (1975)

    Article  Google Scholar 

  57. Gorodetsky, M., Luz, Z., Mazur, Y.: J. Am. Chem. Soc. 89, 1183 (1967)

    Article  CAS  Google Scholar 

  58. Shapet'ko, N. N., Berestova, S. S., Lukovkin, G. M., Bogachev, Yu. S.: Org. Mag. Res. 7, 237 (1975)

    Article  Google Scholar 

  59. Berestova, S. S., Shapet'ko, N. N., Shigorin, D. N., Medvedeva, V. G., Skoldinov, A. P., Plakhina, G. D., Andreichikov, Yu. S.: Theoret & Exper. Chem. 15, 449 (1979); transl. of Teoret. Eksp. Khim. 15, 575 (1979)

    Article  Google Scholar 

  60. Shapet'ko, N. N., Berestova, S. S., Medvedeva, V. G., Skoldinov, A. P., Andreichikov, Yu. S.: Doklady Acad. Nauk USSR 234, 566 (1977); transl. of Doklady Acad. Nauk USSR 234, 876 (1977)

    Google Scholar 

  61. Lazaar, K. I., Bauer, S. H.: J. Phys. Chem. 87, 2411 (1983)

    Article  CAS  Google Scholar 

  62. Isaacson, A. D., Morokuma, K.: J. Am. Chem. Soc. 97, 4453 (1975)

    Article  CAS  Google Scholar 

  63. Chan, S. I., Lin, L., Clutter, D., Dea, P.: Proc. Nat. Acad. Sci. 65, 816 (1970)

    Article  CAS  Google Scholar 

  64. Shapet'ko, N. N., Bogachev, Yu. S., Radushnova, I. L., Shigorin, D. N.: Doklady Acad. Nauk USSR 231, 1085 (1976); transl. of Doklady Acad. Nauk USSR 231, 409 (1976)

    Google Scholar 

  65. Altman, L. A., Laungani, D., Gunnarsson, G., Wennerström, H., Forsén, S.: J. Am. Chem. Soc. 100, 8264 (1978)

    Article  CAS  Google Scholar 

  66. Gunnarsson, G., Wennerström, H., Egan, W., Forsén, S.: Chem. Phys. Letts. 38, 96 (1976)

    Article  CAS  Google Scholar 

  67. Egan, W., Gunnarsson, G., Bull, T. E., Forsén, S.: J. Am. Chem. Soc. 99, 4568 (1977)

    Article  CAS  Google Scholar 

  68. Andreassen, A. L., Zebelman, D., Bauer, S. H.: ibid. 93, 1148 (1971)

    Article  CAS  Google Scholar 

  69. Jones, R. D. G.: Acta Cryst. B32, 1807 (1976)

    CAS  Google Scholar 

  70. Evans, D. F.: J. Chem. Soc. Chem. Comm. 1226 (1982)

    Google Scholar 

  71. Lowrey, A. H., George, C., D'Antonio, P., Karle, J.: J. Am. Chem. Soc. 93, 6399 (1971)

    Article  CAS  Google Scholar 

  72. Andreassen, A. L., Bauer, S. H.: J. Mol. Struct. 12, 381 (1972)

    Article  CAS  Google Scholar 

  73. Abu-Dari, K., Raymond, K. N., Freyberg, D. P.: J. Am. Chem. Soc. 101, 3688 (1979)

    Article  CAS  Google Scholar 

  74. Emsley, J., Jones, D. J., Lucas, L.: Revs. Inorg. Chem. 3, 105 (1981)

    CAS  Google Scholar 

  75. Joswig, W., Fuess, H., Ferraris, G.: Acta Cryst. B 38, 2798 (1982)

    Google Scholar 

  76. Olovsson, I., Jönsson, P.-G.: The Hydrogen Bond, Vol. II, p. 393, Amsterdam, North-Holland Publishing Co. 1976

    Google Scholar 

  77. Engelbretson, G. R., Rundle, R. E.: J. Am. Chem. Soc. 86, 574 (1964)

    Article  Google Scholar 

  78. Williams, D. E., Dumke, W. L., Rundle, R. E.: Acta Cryst. 15, 627 (1962)

    Article  CAS  Google Scholar 

  79. Schaefer, J. P., Wheatley, P. J.: J. Chem. Soc. (A) 528 (1966)

    Google Scholar 

  80. Norrestam, R., von Glehn, M., Wachtmeister, C. A.: Acta Chem. Scand. 28 B, 1149 (1974)

    Google Scholar 

  81. Camerman, A., Mastropaolo, D., Camerman, N.: J. Am. Chem. Soc. 105, 1584 (1983)

    Article  CAS  Google Scholar 

  82. Power, L. F., Jones, R. D. G.: Acta Cryst. B 27, 181 (1971)

    Google Scholar 

  83. Semmingsen, D.: Acta Chem. Scand. 26, 143 (1971)

    Google Scholar 

  84. Jones, R. D. G.: Acta Cryst. B 32, 2133 (1976)

    Google Scholar 

  85. Hollander, F. J., Templeton, D. H., Zalkin, A.: ibid. B 29, 1552 (1973)

    Google Scholar 

  86. Jones, R. D. G.: ibid. B 32, 1807 (1976)

    Google Scholar 

  87. Jones, R. D. G.: ibid. B 32, 301 (1976)

    Google Scholar 

  88. Jones, R. D. G.: J. Chem. Soc. Perkin Trans 2 513 (1976)

    Google Scholar 

  89. Haddon, R. C.: J. Am. Chem. Soc. 102, 1807 (1980)

    Article  CAS  Google Scholar 

  90. Lingafelter, E. C., Braun, R. L.: ibid. 88, 2951 (1966)

    Article  CAS  Google Scholar 

  91. Singh, T. R., Wood, J. L.: J. Chem. Phys. 50, 3572 (1969)

    Article  CAS  Google Scholar 

  92. Emsley, J., Jones, D. J., Kuroda, R.: J. Chem. Soc. Dalton Trans 2141 (1981)

    Google Scholar 

  93. Rowe, W. F. Jr., Duerst, R. W., Wilson, E. B.: J. Am. Chem. Soc. 98, 4021 (1976)

    Article  CAS  Google Scholar 

  94. Baughaun, S. L., Duerst, R. W., Rowe, W. F., Smith, I., Wilson, E. B.: ibid. 103, 6296 (1981)

    Article  Google Scholar 

  95. Turner, P. H.: J. Chem. Soc. Faraday Trans 2 76, 383 (1980)

    Article  CAS  Google Scholar 

  96. Sanders, N. D.: J. Mol. Spectrosc. 86, 27 (1981)

    Article  CAS  Google Scholar 

  97. Brown, R. S.: J. Am. Chem. Soc. 99, 5497 (1977)

    Article  CAS  Google Scholar 

  98. Seliskar, C. J., Hoffman, R. E.: Chem. Phys. Letts. 43, 481 (1976)

    Article  CAS  Google Scholar 

  99. Seliskar, C. J., Hoffman, R. E.: J. Am. Chem. Soc. 99, 7072 (1977)

    Article  CAS  Google Scholar 

  100. Bicerano, J., Shaefer, H. F. III, Miller, W. H.: ibid. 105, 2550 (1983)

    Article  CAS  Google Scholar 

  101. Pople, G. A., Santry, D. P., Segal, G. A.: J. Chem. Phys. 44, 3289 (1966)

    Article  CAS  Google Scholar 

  102. Schuster, P.: Chem. Phys. Letts. 3, 433 (1969)

    Article  CAS  Google Scholar 

  103. Gordon, M. S., Koob, R. D.: J. Am. Chem. Soc. 95, 5863 (1973)

    Article  CAS  Google Scholar 

  104. Karlström, G., Wennerström, H., Jönsson, B., Forsén, S., Almlöf, J., Roos, B.: ibid. 97, 4188 (1975)

    Article  Google Scholar 

  105. Karlström, G., Jönsson, B., Roos, B., Wennerström, H.: ibid. 98, 6851 (1976)

    Article  Google Scholar 

  106. Del Bene, J. E., Kochenour, W. L.: ibid. 98, 2041 (1976)

    Article  Google Scholar 

  107. Fluder, E. M., de la Vega, J. R.: ibid. 100, 5265 (1978)

    Article  CAS  Google Scholar 

  108. Bouma, W. J., Vincent, M. A., Radom, L.: Int. J. Quantum Chem. 14, 767 (1978)

    Article  CAS  Google Scholar 

  109. Catalán, J., Yánez, M., Fernández, J. I.: J. Am. Chem. Soc. 100, 6917 (1978)

    Article  Google Scholar 

  110. Emsley, J., Overill, R. E., Parker, R. J.: J. Chem. Soc. Faraday 2 79, 1347 (1983)

    Article  CAS  Google Scholar 

  111. Emsley, J., Overill, R. E.: Chem. Phys. Letts. 65, 616 (1979); Bouma, W. J., Radom, L.: ibid. 64, 216 (1979)

    Article  CAS  Google Scholar 

  112. Melia, T. P., Merrifield, R.: J. Applied Chem. 19, 79 (1969)

    Article  CAS  Google Scholar 

  113. Bouma, W. J., Radom, L.: Australian J. Chem. 31, 1649 (1978)

    Article  CAS  Google Scholar 

  114. Noack, W.-E.: Theoret. Chim. Acta 53, 101 (1979)

    Article  CAS  Google Scholar 

  115. Carlsen, L., Duus, F.: J. Chem. Soc. Perkin Trans 2 1081 (1980)

    Google Scholar 

  116. Larson, J. W., McMahon, T. B.: J. Am. Chem. Soc. 104, 5848 (1982)

    Article  CAS  Google Scholar 

  117. Kopteva, T. S., Shigorin, D. N.: Russ. J. Phys. Chem. 48, 312 (1974); transl. Zhur. Fizich. Khim. 48, 532 (1974)

    Google Scholar 

  118. Kreevoy, M. M., Liang, T. M., Chang, K.-C.: J. Am. Chem. Soc. 99, 5207 (1977)

    Article  CAS  Google Scholar 

  119. Kreevoy, M. M., Liang, T. M.: ibid. 102, 3315 (1980)

    Article  CAS  Google Scholar 

  120. Kreevoy, M. M., Ridl, B. A.: J. Phys. Chem. 85, 914 (1981)

    Article  CAS  Google Scholar 

  121. Ernstbrunner, E. E.: J. Chem. Soc. A 1558 (1970)

    Google Scholar 

  122. Hadzi, D., Bratos, S.: The Hydrogen Bond, Vol. II, Chap. 12, p. 567, Amsterdam, North-Holland Publishing Co. 1976

    Google Scholar 

  123. Ogoshi, H., Nakamoto, K.: J. Chem. Phys. 45, 3113 (1966)

    Article  CAS  Google Scholar 

  124. Wierzchowski, K. L., Shugar, D.: Spectrochim Acta 21, 943 (1965)

    Article  CAS  Google Scholar 

  125. Tayyari, S. F., Zeegers-Huyskens, Th., Wood, J. L.: ibid. 35 A, 1289 (1979)

    Google Scholar 

  126. Tayyari, S. F., Zeegers-Huyskens, Th., Wood, J. L.: ibid. 35 A, 1265 (1979)

    Google Scholar 

  127. Ogoshi, H., Yoshida, Z.: ibid. 27 A, 165 (1971)

    Google Scholar 

  128. Novak, A.: Structure and Bonding 18, 177 (1974)

    CAS  Google Scholar 

  129. Sherry, A. D.: The Hydrogen Bond, Vol. III, Chap. 25, p. 1199, Amsterdam, North-Holland Publishing Co. 1976

    Google Scholar 

  130. Bratoz, S., Hadzi, D., Rossmy, G.: Trans. Faraday Soc. 52, 464 (1956)

    Article  CAS  Google Scholar 

  131. Hussain, M. S., Schlemper, E. O., Fair, C. K.: Acta Cryst. B 36, 1104 (1980)

    Google Scholar 

  132. Mecke, R., Funck, E.: Z. Elektrochem. Ber. Buns. 60, 1124 (1956)

    CAS  Google Scholar 

  133. Ogoshi, H., Yoshida, Z.: J. Chem. Soc. Chem. Comm. 176 (1970)

    Google Scholar 

  134. Kato, S., Kato, H., Fukui, K.: J. Am. Chem. Soc. 99, 684 (1977)

    Article  CAS  Google Scholar 

  135. Bell, R. P.: The Tunnel Effect in Chemistry, London, Chapman & Hall, 1980

    Google Scholar 

  136. de la Vega, J. R.: Acc. Chem. Res. 15, 185 (1982)

    Article  Google Scholar 

  137. Burch, J. H., Fluder, E. M., de la Vega, J. R.: J. Am. Chem. Soc. 102, 4000 (1980)

    Article  Google Scholar 

  138. de la Vega, J. R., Busch, J. H., Schauble, J. H., Kunze, K. L., Haggert, B. E.: ibid. 104, 3295 (1982)

    Article  Google Scholar 

  139. Shiau, W.-I., Duesler, E. N., Paul, I. C., Curtin, D. Y., Blann, W. G., Fyfe, C. A.: ibid. 102, 4546 (1980) and refs. therein

    Article  CAS  Google Scholar 

  140. Bratan, S., Strohbusch, F.: J. Mol. Struct. 61, 409 (1980)

    Article  CAS  Google Scholar 

  141. Moore, R. E., Scheuer, P. G.: J. Org. Chem. 31, 3272 (1966)

    Article  CAS  Google Scholar 

  142. Snyder, W. R., Schreiber, H. D., Spencer, J. N.: Spectrochim. Acta 29 A, 1225 (1973)

    Google Scholar 

  143. Duus, F., Lawesson, S.-O.: Arkiv Kemi 29, 127 (1968)

    CAS  Google Scholar 

  144. Nørskov-Lauritsen, L., Carlsen, L., Duus, F.: J. Chem. Soc. Chem. Comm. 496 (1983)

    Google Scholar 

  145. Carlsen, L., Duus, F.: J. Chem. Soc. Perkin Trans 2 1080 (1980)

    Google Scholar 

  146. Carlsen, L., Duus, F.: ibid. 2 1532 (1979)

    Google Scholar 

  147. Gebicki, J., Krantz, A.: J. Chem. Soc. Chem. Comm. 486 (1981); J. Am. Chem. Soc. 103, 4521 (1981)

    Google Scholar 

  148. Duus, F., Anthonsen, J. W.: Acta Chem. Scand. 31, 40 (1977)

    Article  Google Scholar 

  149. Jørgensen, F. S., Brown, R. S., Carlsen, L., Duus, F.: J. Am. Chem. Soc. 104, 5922 (1982)

    Article  Google Scholar 

  150. Carlsen, L., Duus, F.: J. Chem. Soc. Perkin Trans. 2 1768 (1980)

    Google Scholar 

  151. Duus, F.: J. Org. Chem. 42, 3123 (1977)

    Article  CAS  Google Scholar 

  152. Alves, A. C. P., Hollas, J. M.: Mol. Physics 23, 927 (1972); ibid. 25, 1305 (1973)

    Article  CAS  Google Scholar 

  153. Woolfe, G. J., Thistlethwaite, P. J.: J. Am. Chem. Soc. 103, 6916 (1981)

    Article  CAS  Google Scholar 

  154. Pickett, H. M.: ibid. 95, 1770 (1973)

    Article  CAS  Google Scholar 

  155. Rossetti, R., Rayford, R., Haddon, R. C., Brus, L. E.: ibid. 103, 4303 (1981)

    Article  CAS  Google Scholar 

  156. Hibbert, F., Simpson, G. R.: ibid. 105, 1063 (1983)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, King’s College, WC2R 2LS, Strand, London, U.K.

    John Emsley

Authors
  1. John Emsley
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 1984 Springer-Verlag

About this paper

Cite this paper

Emsley, J. (1984). The composition, structure and hydrogen bonding of the β-diketones. In: Complex Chemistry. Structure and Bonding, vol 57. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0111456

Download citation

  • DOI: https://doi.org/10.1007/BFb0111456

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-13411-4

  • Online ISBN: 978-3-540-38948-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation