Skip to main content
SpringerLink
Log in

Is Polymorphism Caused by Molecular Conformational Changes?

  • Conference paper
Book cover Models, Mysteries and Magic of Molecules

Abstract

The possibility that polymorphism is connected with variations of molecular conformations within a unit cell is explored graphically and numerically. The conclusion is that no direct relationship exists between one and the other because polymorphic crystals are found, equally frequently, in which the conformations of their molecules agree almost exactly, or agree somewhat, or display large differences

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 189.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 249.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 249.99
Price excludes VAT (USA)
  • Durable hardcover 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. J. Bernstein, Polymorphism in Molecular Crystals, Oxford, Oxford University Press, 2002.

    Google Scholar 

  2. G. R. Desiraju, Crystal Engineering—the design of organic solids, Material Science Monographs, Vol. 54, Elsevier. Amsterdam, The Netherlands, 1989.

    Google Scholar 

  3. Cambridge Structural Database, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ UK, Tel, = +44-1223-336408. Available from http://www.ccdc.cam.ac.uk Released by Wavefunction, Inc. 18401 von Karman Ave., Suite 370, Irvine CA 92612, Tel. = 949-955-2120. Fax = 949-955-2118. http://www.wavefun.com. Version 1.8, 2005.

    Google Scholar 

  4. MATCHIT is a program for the graphical and mathematical superposition of molecules or fragments that are chemically related, performing a least-square fit of designated atoms and calculating the distances between related pairs of atoms. It was written at the University of Houston Chemistry Department by Rathnakumar Ramanujam, under the guidance of Ivan Bernal, 2002 and 2003.

    Google Scholar 

  5. M. Lutz, A. L. Spek, P. de Hoog, P. Gamez, W. L. Driessen and J. Reedjik, Private Communication to CSD, 2002.

    Google Scholar 

  6. N. V. Podberezskaya, T. P. Shakhshneider, A. V. Virovets and P. A. Stabnikov, Zh. Strukt. Khim. (Russ.) (J. Struct. Chem.), 32, 96 (1991).

    CAS  Google Scholar 

  7. S. Geremia, R. Dreos, L. Randaccio, G. Tauzher and L. Antolini, Inorg. Chim. Acta, 216, 125 (1994).

    Google Scholar 

  8. Yu. M. Chumakov, V. N. Biyushkin, V. I. Tsapkov, M. V. Gandzii, N. M. Samus’ and T. I. Malinovskii, Koord. Khim.(Russ.) (Coord. Chem.), 20, 381 (1994).

    Google Scholar 

  9. H. Chun, B. J. Salinas and I. Bernal, Eur. J. Inorg. Chem., 723 (1999).

    Google Scholar 

  10. I. Bernal, J. Cetrullo and J. Cai, Trans. Met. Chem., 19, 221 (1994). This crystal contains two molecules in the symmetric unit—see the next reference.

    Google Scholar 

  11. I. Bernal, J. Cetrullo and J. Cai, Trans. Met. Chem., 19, 221 (1994). Of two molecules in the asymmetric unit, this is the second.

    Google Scholar 

  12. L. F. Power, K. E. Turner and F. H. Moore, Acta Crystallogr., B32, 11 (1974).

    Google Scholar 

  13. A. Kvick, W. M. Canning and T. F. Koetzle, Acta Crystallogr., B36, 115 (1980).

    Google Scholar 

  14. T. N. Debrushchak, E. V. Boldyreva and E. S. Shutova, Acta Crystallogr., E58, o634 (2002).

    Google Scholar 

  15. M. T. Averbuch-Puchot, Z. Kristallogr., 207, 111 (1993).

    Google Scholar 

  16. J. J. Madden. E. L. McGandy and N. C. Seeman, Acta Crystallogr., B28, 2377 (1972).

    Google Scholar 

  17. C. H. Gorbitz and B. Dalhus, Acta Crystallogr., C31, 2022 (1975).

    Google Scholar 

  18. K. A. Kerr, J. P. Ashmore and T. F. Koetzle, Acta Crystallogr., B51, 1059 (1995).

    Google Scholar 

  19. W. Marcoin, H. Dude, J. Kusz and B. Bzowski, Applied Crytallogr. Conference, p. 40 (1999).

    Google Scholar 

  20. N. Hiyayama. K. Shibata. Y. Ohashi and Y. Sasada, Bull. Chem. Soc. Japan, 53, 30 (1980).

    Article  Google Scholar 

  21. R. Jones, J. R. Scheffer, J. Trotter and Jie Yang, Crystallogr., Sect. B: Struct. Sci., 50, 601 (1994).

    Article  Google Scholar 

  22. JUHMAA10 No reference is available in CSD.

    Google Scholar 

  23. M. Yu. Antipin, T. V. Timofeeva, R. D. Clark, V. N. Nesterov, F. M. Dolgushin, J. Wu, and A. Leyderman, J. Mater. Chem., 11, 351 (2001).

    Google Scholar 

  24. R. Dreos-Garlatti, S. Geremia, L. Randaccio, S. Ruffini and G. Tauzher, J. Organomet. Chem., 487, C24 (1995).

    Article  CAS  Google Scholar 

  25. B. M. Craven and E. A. Vizzini, ActaCrystallogr., Sect. B: Struct. Crystallogr., Cryst. Chem., 25, 1993 (1969).

    Article  CAS  Google Scholar 

  26. B. M. Craven, E. A. Vizzini and M. M. Rodrigues, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem., 25, 1978 (1969).

    Article  CAS  Google Scholar 

  27. R. K. McMullan, R. O. Fox Jr and B. M. Craven, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem., 34, 3719 (1978).

    Google Scholar 

  28. B. M. Gatehouse, Cryst. Struct. Commun., 11, 493 (1982).

    CAS  Google Scholar 

  29. E. Silina, Yu. Bankovsky, V. Belsky and J. Lejejs, Latv. Khim. Z. (Latvian J. Chem.), 155 (1994).

    Google Scholar 

  30. P. L. Johnson, C. J. Cheer, J. P. Schaefer, V. J. James and F. H. Moor, Tetrahedron, 28, 2893 (1972).

    Article  CAS  Google Scholar 

  31. M. Spiniello and J. M. White, Org. Biomol. Chem, 1, 3094 (2003).

    Article  CAS  Google Scholar 

  32. S. M. Reutzel-Edens, J. K. Bush, P. A. Magee, G. A. Stephenson and S. R. Byrn, Cryst. Growth Des., 3, 897 (2003).

    Article  CAS  Google Scholar 

  33. I. Wawrzycka-Gorczyca, A. E. Koziol and M. Glice, J. Cybulski, Acta Crystallogr., Sect. E: Struct. Rep. Onlin, 60, o66 (2004).

    Article  CAS  Google Scholar 

  34. F. Watjen, R. Baker, M. Engelstoff, R. Herbert, A. MacLeod, A. Knight, K. Merchant, J. Moseley, J. Saunders, C. J. Swain, E. Wong and J. P. Springer, J. Med. Chem., 32, 2282 (1989).

    Article  CAS  Google Scholar 

  35. F. Takusagawa and T. F. Koetzle, Acta Crystallogr., Sect. B, Struct. Crystallogr. Cryst. Chem., 35, 2888 (1979).

    Article  Google Scholar 

  36. G. J. Palenik, Inorg. Chem., 8, 2744 (1969).

    Article  CAS  Google Scholar 

  37. D. Braga, M. Polito, M. Bracaccini, D. D’Addario, E. Tagliavini, L. Sturba and F. Grepioni, Organometallics, 22, 2142 (2003).

    Article  CAS  Google Scholar 

  38. K. Onitsuka, Xin-Qung Tao, Wen-Qing Wang, Y. Otsuka, K. Sonogashira, T. Adachi and T. Yoshida, J. Organomet. Chem., 473, 195 (1994).

    CAS  Google Scholar 

  39. E. Champeil and S. M. Draper, J. Chem. Soc., Dalton Trans., 1440 (2001).

    Google Scholar 

  40. Ya. M. Nagiev, A. N. Shnulin, Sh. T. Bagirov, V. A. Adigezalov, V. I. Shil‘nikov and I. M. Mamedov, Zh. Strukt. Khim. (Russ.) (J. Struct. Chem.), 29, 105 (1988).

    Google Scholar 

  41. A. N. Shnulin, Ya. M. Nagiev, Sh. T. Bagirov, V. A. Adigezalov, V. I. Shil‘nikov and I. M. Mamedov, Kristallografiya (Russ.) (Crystallogr. Rep.), 34, 96 (1989).

    Google Scholar 

  42. D. M. M. Farrell, C. Glidewell, J. N. Low, J. M. S. Skakle and C. M. Zakaria, Acta Crystallogr., Sect. B: Struct. Sci., 58, 289 (2002).

    Article  CAS  Google Scholar 

  43. J. M. S. Skakle, J. L. Wardell, J. N. Low and C. Glidewell, Acta Crystallogr.,Sect. C: Cryst. Struct. Commun., 57, 742 (2001).

    Article  CAS  Google Scholar 

  44. N. Ehlinger and M. Perrin, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 51, 1846 (1995).

    Article  Google Scholar 

  45. K. Ejsmont, M. Broda, A. Domanski, J. B. Kyziol and J. Zaleski, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 58, o545 (2002).

    Google Scholar 

  46. H.-D. Becker, S. R. Hall, B. W. Skelton and A. H. White, Aust. J. Chem., 35, 2357 (1982).

    Article  CAS  Google Scholar 

  47. P. J. Cox, A. T. Md. Anisuzzaman, R. H. Pryce-Jones, G. G. Skellern, A. J. Florence and N. Shankland, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 54, 856 (1998).

    Google Scholar 

  48. P. J. Cox and J. L. Wardell, Int. J. Pharmaceutics, 194, 147 (2000).

    Article  CAS  Google Scholar 

  49. P. D. Cookson, E. R. T. Tiekink and M. W. Whitehouse, Aust. J. Chem., 47, 577 (1994).

    Article  CAS  Google Scholar 

  50. B. R. Vincent, D. J. Clarke, D. R. Smyth, D. de Vos and E. R. T. Tiekink, Met.-Based Drugs, 8, 79 (2001).

    Google Scholar 

  51. F. R. Fronczek, A. G. Ober and N. H. Fischer, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 43, 358 (1987).

    Article  Google Scholar 

  52. U. Rychlewska, M. Budesinsky, B. Szczepanska, E. Bloszyk and M. Holub, Collect. Czech. Chem. Commun., 60, 276 (1995).

    Article  CAS  Google Scholar 

  53. K. Go, G. Kartha and N. Viswanathan, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 41, 417 (1985).

    Article  Google Scholar 

  54. K. Sada, T. Kondo, M. Ushioda, Y. Matsuura, K. Nakano, M. Miyata and K. Miki, Bull. Chem. Soc. Jpn., 71, 1931 (1998).

    Article  CAS  Google Scholar 

  55. R. D. Gilardi and R. J. Butcher, J. Chem. Cryst., 28, 673 (1998).

    Article  CAS  Google Scholar 

  56. K. Reichenbacher, H. I. Suss, H. Stoeckli-Evans, S. Bracco, P. Sozzani, E. Weber, J. Hulliger, New J. Chem. (Nouv. J. Chim.), 28, 393 (2004).

    Google Scholar 

  57. A. Anthony, G. R. Desiraju, R. K. R. Jetti, S. S. Kuduva, N. N. L. Madhavi, A. Nangia, R. Thaimattam, V. R. Thalladi, Crystal Engineering, 1, 1 (1998).

    Article  CAS  Google Scholar 

  58. D. L. Cullen, E. F. Meyer Jr, J. Am. Chem. Soc., 96, 2095 (1974).

    Article  CAS  Google Scholar 

  59. E. F. Meyer Jr, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem., 28, 2162 (1972).

    Article  CAS  Google Scholar 

  60. T. Chivers, M. Parvez, I. Vargas-Baca and G. Schatte, Can. J. Chem., 76, 1093 (1998).

    Article  CAS  Google Scholar 

  61. Z. Tao, Q.-J. Zhu, S.-F. Xie, X.-Q. Luo, G.-Y. Zhang, Z.-Y. Zhou and X.-G. Zhou, Chin., J. Inorg. Chem., 18, 147, (2002).

    CAS  Google Scholar 

  62. D. A. Buckingham, J. D. Edwards and G. McLaughlin, Inorg. Chem., 21, 2770, (1982).

    Article  CAS  Google Scholar 

  63. L. Yu, G. A. Stephenson, C. A. Mitchel, C. A. Burrell, S. V. Norek, J. J. Bowyer, T. B. Borchardt, J. G. Stowell and S. R. Bryn, J. Amer. Chem. Soc., 122, 585 (2000).

    Article  CAS  Google Scholar 

Download references

Authors
  1. Ivan Bernal
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. University of Pretoria, South Africa

    Jan C.A. Boeyens

  2. Universidad de Costa Rica, Costa Rica

    J.F. Ogilvie

Rights and permissions

Reprints and permissions

Copyright information

© 2008 Springer

About this paper

Cite this paper

Bernal, I. (2008). Is Polymorphism Caused by Molecular Conformational Changes?. In: Boeyens, J.C., Ogilvie, J. (eds) Models, Mysteries and Magic of Molecules. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-5941-4_6

Download citation

Publish with us

Policies and ethics

Search

Navigation