Skip to main content
SpringerLink
Log in

Reactivity in Solid State and Electron Deformation Density Determinations

  • Chapter
Book cover Intermolecular Interactions

  • 140 Accesses

Abstract

This contribution consists of three related topics. After some introductory remarks about the techniques used for Electron Deformation Density Determinations (EDD) the next part is concerned with the solid state photochemistry of styryl-α-pyrone and their isoelectronic nitrogen substituted isomorphs. Investigations of the EDD provide an explanation for the change in photoreactivity, since different forms of conjugation within the molecules as well as different π-π-interactions in the solid state are present.

In the second part of the contribution results on the structural and reactivity investigations of several organic di- and polyenes which are liquids at ambient temperature will be presented. A short description of the techniques of in situ crystal growing used at low temperature will be followed by a summary of recent results. The photoreactivity of single crystals as grown on a diffractometer has been directly investigated and analysed using various techniques.

Similar crystal growing techniques have been used to characterize numerous substituted phosphines in the solid state. The derived results as presented in the third part of the paper will give a more detailed insight into the chemical properties of these ligands which are popular in transition metal catalysis.

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. H. Tromsdorff, Ann. Chem. Pharm. 11:190 (1834).

    Article  Google Scholar 

  2. W. Heldt, Ann. Chem. Pharm. 63:10 (1847).

    Article  Google Scholar 

  3. C. Liebermann, Chem. Ber. 10:2177 (1877).

    Article  Google Scholar 

  4. C. Liebermann and M. Illinski, Chem. Ber. 18:3193 (1885).

    Article  Google Scholar 

  5. C. Liebermann, Chem. Ber. 28:316 (1895).

    Article  Google Scholar 

  6. J. Bertram and R. Kürsten, J. Prakt. Chem. 51:316 (1895).

    Article  Google Scholar 

  7. H. I. Bernstein and W. C. Quimby, J. Am. Chem. Soc. 65:1845 (1943).

    Article  Google Scholar 

  8. G. M. J. Schmidt. “Solid State Photochemistry”, Verlag Chemie, Weinheim (1976).

    Google Scholar 

  9. R. E. Pincock, K. R. Wilson and T. E. Kiovsky, J. Am. Chem. Soc. 89:6890 (1967).

    Article  Google Scholar 

  10. S. Okamura, K. Hayashi and Y. Kitanishi, J. Polym. Sci. 58:925 (1962).

    Article  ADS  Google Scholar 

  11. P. Yates and P. Singh, J. Org. Chem. 34:4052 (1969).

    Article  Google Scholar 

  12. C. N. Sukenik, J. A. P. Mandel, N. S. Lau and R. G. Bergman, J. Am. Chem. Soc. 97:851 (1977).

    Article  Google Scholar 

  13. A. Gavezzotti and M. Simonetta, Chem. Rev. 82:1 (1982).

    Article  Google Scholar 

  14. V. Ramamurthy and K. Venkatesan, Chem. Rev. 87:433 (1987).

    Article  Google Scholar 

  15. N. B. Singh, R. J. Singh and N. P. Singh, Tetrahedron 50:6441 (1994).

    Article  Google Scholar 

  16. F. Toda, Acc. Chem. Res. 28:480 (1995).

    Article  Google Scholar 

  17. K. Angermund, I. Klopp, C. Krüger and M. Nolte, Angew. Chem. Int. Ed. Engl. 30:1345 (1991).

    Article  Google Scholar 

  18. I. Ortmann, PhD Thesis, Max-Planck-Institut für Kohlenforschung and University of Wuppertal (1990).

    Google Scholar 

  19. P. Debye and P. Scherrer, Phys. Z. 19:474 (1918).

    Google Scholar 

  20. A. Hartman and F. L. Hirshfeld, Acta Cryst. 20:80 (1966).

    Article  Google Scholar 

  21. For reviews, see: (a) P. Coppens and M. B. Hall. “Electron Distributions and the Chemical Bond”, Springer Science+Business Media New York (1982).

    Book  Google Scholar 

  22. P. Coppens, Angew. Chem. Int. Ed. Engl. 16:32 (1977).

    Article  Google Scholar 

  23. K. Angermund, K.H. Claus, R. Goddard and C. Krüger, Angew. Chem. Int. Ed. Engl. 24:237 (1985).

    Article  Google Scholar 

  24. M. Breitenstein, H. Dannöhl, H. Meyer, A. Schweig, R. Seeger, U. Seeger and W. Zittlau, Int. Rev. Phys. Chem. 3:335 (1983) and references cited therein.

    Article  Google Scholar 

  25. R. F. W. Bader and W. H. Henneker, J. Chem. Phys. 46:3341 (1967).

    Article  ADS  Google Scholar 

  26. M. Benard, J. Am. Chem. Soc. 100:7740 (1978).

    Article  Google Scholar 

  27. F. L. Hirshfeld and S. Rzotkiewicz, Mol. Phys. 27:1319 (1974).

    Article  ADS  Google Scholar 

  28. J. W. Chinn, Jr. and M. B. Hall, Organometallics 3:284 (1984).

    Article  Google Scholar 

  29. J. W. Chinn, Jr. and M. B. Hall, J. Am. Chem. Soc. 105:4930 (1983).

    Article  Google Scholar 

  30. P. Coppens and E. D. Stevens, Adv. Quantum Chem. 10:1 (1977).

    Article  ADS  Google Scholar 

  31. K. Hermansson and I. Olovsson, Theor. Chim. Acta 64:265 (1984).

    Article  Google Scholar 

  32. R. F. Stewart and M. A. Spackman, in: “Structure and Bonding in Crystals”, vol. 1, M.O. Keefe and A. Navrotsky, eds., Academic Press, New York (1981).

    Google Scholar 

  33. For a review, see (a) J. D. Dunitz. “X-Ray Analysis and the Structure of Organic Molecules”, Cornell University Press, Ithaca, NY, (1979)

    Google Scholar 

  34. G. J. H. van Ness and A. Vos, Acta Cryst. B34:1947 (1978).

    Google Scholar 

  35. J. Lewis, D. Schwarzenbach and H. D. Flack, Acta Cryst. A38:733 (1982).

    Google Scholar 

  36. K. Hino, Y. Saito and M. Benard, Acta Cryst. B37:2164 (1981).

    Google Scholar 

  37. A. Mitschler, B. Rees, R. Wiest and M. Benard, J. Am. Chem. Soc. 104:7501 (1982).

    Article  Google Scholar 

  38. H. Dietrich and C. Scheringer, Acta Cryst. B35:1191 (1979).

    Google Scholar 

  39. A. Kirfel, G. Will, R.F. Stewart, Acta Cryst. B39:175 (1983).

    Google Scholar 

  40. B. Jahn, H. Dreeskamp, Ber. Bunsenges. Phys. Chem. 88:42 (1984).

    Article  Google Scholar 

  41. H. Dreeskamp, B. Jahn and J. Pabst, Z. Naturforsch. A 36:665 (1981).

    ADS  Google Scholar 

  42. K. Angermund, R. Goddard and C. Krüger, Acta Cryst. A40:C162 (1984) (Suppl.).

    Google Scholar 

  43. F.L. Hirshfeld, Theor. Chim. Acta 44:129 (1977).

    Article  Google Scholar 

  44. J.-M. Savariault, M. S. Lehmann, J. Am. Chem. Soc. 102:1298 (1980).

    Article  Google Scholar 

  45. J. D. Dunitz, W. B. Schweizer and P. Seiler, Helv. Chim. Acta 66:123 (1983).

    Article  Google Scholar 

  46. J. D. Dunitz and P. Seiler, J. Am. Chem. Soc. 105:7056 (1983).

    Article  Google Scholar 

  47. W.H.E. Schwarz, P. Valtazanos and K. Ruedenberg, Theor. Chim. Acta 68:471 (1985).

    Article  Google Scholar 

  48. W.H.E. Schwarz, K. Ruedenberg and L. Mensching, J. Am. Chem. Soc. 111:6926 (1989).

    Article  Google Scholar 

  49. L. Mensching, W. von Niessen, P. Valtazanos, K. Ruedenberg and W H.E. Schwarz, J. Am. Chem. Soc. 111:6933 (1989).

    Article  Google Scholar 

  50. W.H.E. Schwarz, L. Mensching, K. Ruedenberg, P. Valtazanos, L.L. Miller and W von Niessen, Angew. Chem. 101:605 (1989).

    Article  Google Scholar 

  51. A. Hartman and F. L. Hirshfeld, Acta Cryst. 20:80 (1966).

    Article  Google Scholar 

  52. A.M. O’Connell, A.I.M. Rae and E. N. Maslen, Acta Cryst. 21:208 (1966).

    Article  Google Scholar 

  53. P. Coppens, Science 158:1577 (1967).

    Article  ADS  Google Scholar 

  54. P. Coppens, T.M. Sabine, R.G. Delaplane and J. A. Ibers, Acta Cryst. B25:2451 (1969).

    Google Scholar 

  55. P. Coppens and A. Vos, Acta Cryst. B27:146 (1971).

    Google Scholar 

  56. D.A. Matthews and G. D. Stucky, J. Am. Chem. Soc. 93:5954 (1971).

    Article  Google Scholar 

  57. R. Brill, H. Dietrich and H. Dierks, Acta Cryst. B27:2003 (1971).

    Google Scholar 

  58. J. M. Savariault and M. S. Lehmann J. Am. Chem. Soc. 102:1298 (1980).

    Article  Google Scholar 

  59. M. A. Spackmann and P. G. Byrom, Acta Cryst. B53:553 (1997) and literature quoted therein. For multipolar refinement see also

    Google Scholar 

  60. F. L. Hirshfeld, Acta Cryst. B27:769 (1971).

    Google Scholar 

  61. R. F. Steward, J. Chem. Phys. 51:4569 (1969).

    Article  ADS  Google Scholar 

  62. R. F. Steward, J. Chem. Phys. 57:1664 (1972).

    Article  ADS  Google Scholar 

  63. R. F. Steward, J. Chem. Phys. 58:1668 (1973).

    Article  ADS  Google Scholar 

  64. R. F. Steward, Acta Cryst. A32:565 (1976).

    Google Scholar 

  65. R. F. Steward, E. R. Davidson and W. T. Simpson, J. Chem. Phys. 42:3175 (1965).

    Article  ADS  Google Scholar 

  66. R. J. van der Wal and R. F. Steward, Acta Cryst. A39:422 (1983).

    Google Scholar 

  67. R. J. van der Wal and R. F. Steward, Acta Cryst. A40:587 (1984).

    Google Scholar 

  68. N. K. Hansen and P. Coppens, Acta Cryst. A34:909 (1978).

    Google Scholar 

  69. A. S. Brown and M. A. Spackman, Acta Cryst. A47:21 (1991).

    Google Scholar 

  70. A. Holladay, P. Leung and P. Coppens, Acta Cryst. A39:377 (1983).

    Google Scholar 

  71. A. Paturle and P. Coppens, Acta Cryst. A44:6 (1988).

    Google Scholar 

  72. P. Moeckli, D. Schwarzenbach, H.-B. Bürgi, J. Häuser and B. Deley, Acta Cryst. B44:636 (1988).

    Google Scholar 

  73. G. C. Verschoor and E. Keulen, Acta Cryst. B27:134 (1971).

    Google Scholar 

  74. K. H. Claus, R. Gerhard and C. Krüger. Martinsrieder Symposium über apparative Entwicklungen in der Röntgen-and Neutronen-Strukturanalyse (1981).

    Google Scholar 

  75. D. Zobel, R. Flaig, P. Luger and H.-G. Krane, Acta Cryst. A52:C26 (1997).

    Google Scholar 

  76. C. Krüger, K. Angermund, J. Bruckmann, F. Lutz and C. Kopiske, Acta Cryst. A52:C285 (1996).

    Google Scholar 

  77. P. Coppens, A CA Newsletter 15:3 (1984).

    Google Scholar 

  78. P. J. Becker, P. Coppens and F. L. Hirshfeld, J. Appl. Crystallogr. 17:369 (1984).

    Article  Google Scholar 

  79. P. Coppens, J. Dam, S. Harkema, D. Feil, R. Feld, M. S. Lehmann, R. Goddard, C. Krüger, E. Hellner, H. Johansen, F. K. Larsen, T. F. Koetzle, R. K. McMullan, E. N. Maslen and E. D. Stevens, Acta Cryst. A40:184 (1984).

    Google Scholar 

  80. A. A. Pinkerton, C. F. Campana and M. R. Pressprich, Acta Cryst. A52:C26 (1997).

    Google Scholar 

  81. M. Neunhoeffer, H.-D. Clausen, H. Vtter, H. Ohl, C. Krüger and K. Angermund, Liebigs Ann. Chem. 1732 (1985).

    Google Scholar 

  82. K. Angermund, PhD Thesis, Max-Planck-Institut für Kohlenforschung and University of Wuppertal (1986).

    Google Scholar 

  83. O. Heinemann, PhD Thesis, Max-Planck-Institut für Kohlenforschung and University of Essen (1997).

    Google Scholar 

  84. K. Hermansson and S. Lunell, Acta Cryst. B38:2563 (1982).

    Google Scholar 

  85. I. Olovsson. “Crystal Forces and Hydrogen Bonding. Effect on Charge Density”, Laboratoire de Crystallographie, Centre National de la Recherche Scientifique, Grenoble (1978).

    Google Scholar 

  86. I. Klopp, PhD Thesis, Max-Planck-Institut für Kohlenforschung and University of Wuppertal (1990).

    Google Scholar 

  87. I. Ortmann, S. Werner, C. Krüger, S. Mohr and K. Schaffner, J. Am. Chem. Soc. 114:5048 (1992).

    Article  Google Scholar 

  88. R. Boese and D. Blser, J. Appl. Cryst. 22:394 (1989).

    Article  Google Scholar 

  89. H. Hope, Acta Cryst. B44:22 (1988).

    Google Scholar 

  90. T. Kottke and D. Stalke, J. APPl. Cryst. 26:615 (1993).

    Article  Google Scholar 

  91. M. Veith and W. Frank, Chem. Rev. 88:81 (1988).

    Article  Google Scholar 

  92. M. Renaud and R. Fourme, Bull. Soc. Fr. Mineral. Cryst. 89:243 (1966).

    Google Scholar 

  93. W C. von Dohlen and G. B. Carpenter, Acta Cryst. 8:646 (1955).

    Article  Google Scholar 

  94. D. Brodalla, D. Mootz, R. Boese and W Osswald, J. Appl. Cryst. 18:316 (1985).

    Article  Google Scholar 

  95. K. H. Claus and C. Krüger, Acta Cryst. C44:1632 (1988).

    Google Scholar 

  96. R. Boese and M. Nussbaumer, “In-situ Crystallization Techniques”, vol. 7 of “IUCR Crystallographic Symposia”, Oxford University Press, Oxford, England.

    Google Scholar 

  97. F. Lutz, PhD Thesis, Max-Planck-Institut für Kohlenforschung and University of Wuppertal (1992).

    Google Scholar 

  98. J. Bruckmann, PhD Thesis, Max-Planck-Institut für Kohlenforschung and University of Bochum 1996.

    Google Scholar 

  99. J. D. Dunitz and J. Waser, J. Am. Chem. Soc. 94:5645 (1972).

    Article  Google Scholar 

  100. N. L. Allinger and T. Sprague, Tetrahedron 31:21 (1975).

    Article  Google Scholar 

  101. O. Ermer, Struct. Bonding 27:161 (1976).

    Article  Google Scholar 

  102. F. A. L. Anet and L. Kozerski, J. Am. Chem. Soc. 95:3407 (1973).

    Article  Google Scholar 

  103. B. Bartkowska and C. Krüger, Acta Cryst. C52:1064 (1997).

    Google Scholar 

  104. B. Bartkowska and C. Krüger, Acta Cryst. C52:1066 (1997).

    Google Scholar 

  105. A. Kreuger, Acta. Cryst. 8:348 (1955).

    Article  Google Scholar 

  106. J. C. Huffmann, W. E. Streib and J. M. Müller, Proc. Am. Cryst. Assoc. Ser. 2, 1 156 (1973).

    Google Scholar 

  107. A. Simon, H.-J. Deiseroth, E. Westerbeck and B. Hillenkötter, Z. Anorg. Allg. Chem. 423:203 (1976).

    Article  Google Scholar 

  108. D. Brodalla, D. Mootz, R. Boese and W Osswald, J. Appl. Cryst. 18:316 (1985).

    Article  Google Scholar 

  109. MPI für Kohlenforschung, Dept. of Structural Chemistry, unpublished results

    Google Scholar 

  110. R. Boese. Crystal Growing at Low Temperatures, Praktische Aspekte der Kristallstrukturanalyse, 26.8.-28.8.1994, TU Dresden, Abstract.

    Google Scholar 

  111. see reference 14.

    Google Scholar 

  112. J. Bruckmann, C. Krüger and F. Lutz, Z. Naturforsch. 50b:351 (1995)

    Google Scholar 

  113. J. Bruckmann and C. Krüger, Acta Cryst. C51:1155 (1995).

    Google Scholar 

  114. J. Bruckmann and C. Krüger, Acta Cryst. C52:1733 (1996).

    Google Scholar 

  115. J. Bruckmann and C. Krüger, Acta Cryst. C51:1152 (1995).

    Google Scholar 

  116. J. Bruckmann and C. Krüger, J. Organomet. Chem. 536, 537:565 (1997).

    Article  Google Scholar 

  117. A. H. Cowley, A. Decken, N. C. Norman, C. Krüger, F. Lutz, H. Jacobsen and T. Ziegler, J. Am. Chem. Soc. 119:3389 (1997).

    Article  Google Scholar 

  118. C. A. Tolman, J. Am. Chem. Soc. 92:2956 (1970).

    Article  Google Scholar 

  119. C. A. Tolman, Chem. Rev. 77:313 (1977).

    Article  Google Scholar 

  120. J. Bruckmann, C. Krüger and F. Lutz, Z. Naturforsch. 50b:351 (1995).

    Google Scholar 

  121. J. M. Smith, B. C. Taverner and N. J. Coville, J. Organomet. Chem. 530:131 (1997) and literature quoted therein.

    Article  Google Scholar 

  122. K. Angermund, W. Baumann, E. Dinjus, R. Fornika, H. Görls, M. Kessler, C. Krüger, W. Leitner and F. Lutz, Chem. Eur. J. 3:755 (1997).

    Article  Google Scholar 

  123. M. L. Connolly, J. Applied Cryst. 16:548 (1983).

    Article  Google Scholar 

  124. (b) M. L. Connolly, Science 221:709 (1983).

    Article  ADS  Google Scholar 

  125. K. Angermund, S. Geier, P. W. Jolly, M. Kessler, C. Krüger and F. Lutz, in preparation.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Max-Planck-Institut für Kohlenforschung Strukturchemie Mülheim an der Ruhr, Germany

    Carl Krüger, K. Angermund, B. Bartkowska, J. Bruckmann, K. H. Claus, J. Kuhnigk, F. Lutz & I. Ortmann

Authors
  1. Carl Krüger
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. K. Angermund
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. Bartkowska
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. J. Bruckmann
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. K. H. Claus
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. J. Kuhnigk
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. F. Lutz
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. I. Ortmann
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Free University of Berlin, Berlin, Germany

    Werner Gans

  2. University of the Witwatersrand, Johannesburg, South Africa

    Jan C. A. Boeyens

Rights and permissions

Reprints and permissions

Copyright information

© 1998 Springer Science+Business Media New York

About this chapter

Cite this chapter

Krüger, C. et al. (1998). Reactivity in Solid State and Electron Deformation Density Determinations. In: Gans, W., Boeyens, J.C.A. (eds) Intermolecular Interactions. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4829-4_12

Download citation

  • DOI: https://doi.org/10.1007/978-1-4615-4829-4_12

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-7189-2

  • Online ISBN: 978-1-4615-4829-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation