Skip to main content
SpringerLink
Log in

A new treatment of chemical reactivity: Development of EROS, an expert system for reaction prediction and synthesis design

  • Conference paper
  • First Online:
Organic Synthesis, Reactions and Mechanisms

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 137))

Abstract

An expert system for the prediction of the course of organic chemical reactions and for the design of organic syntheses has been built. It does not depend on a database of chemical reactions. Instead, the system generates reactions from first principles by formal bond- and electron-shifting processes. The reaction sites are found by application of quantitative models for the prediction of chemical reactivity. This approach is founded on procedures that allow rapid calculation of the various physicochemical effects that influence the course of chemical reactions. The extent to which these factors influence chemical reactivity has been studied by statistical methods. Examples of the prediction of quantitative data on chemical reactivity, and of the course of complex organic reactions, are described.

“A theory has only the alternative of being right or wrong. A model has a third possibility — it may be right but irrelevant.”

Manfred Eigen

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.

14 References

  1. Corey, E. J., Dankeiser, R. L. Chandrasekaran, S., Keck, G. E., Gopalan, B., Larsen, S. D., Siret, P., Gras, J.-L.: J. Am. Chem. Soc. 100, 8034–8036 (1978)

    Article  Google Scholar 

  2. For a brief, enlightening discussion see: Turner, S.: The Design of Organic Syntheses, Elsevier, Amsterdam 1976

    Google Scholar 

  3. Corey, E. J.: Pure Appl. Chem. 14, 19–37 (1967)

    Google Scholar 

  4. Warren, S.: Organic Synthesis, The Disconnection Approach, Wiley, Chichester 1982

    Google Scholar 

  5. Gasteiger, J.: Chapter: Syntheseplanung, in: Computer in der Chemie, (Ziegler, E., Ed.), Springer, Heidelberg 1984, p. 207–257

    Google Scholar 

  6. Gasteiger, J., Jochum, C.: Topics Curr. Chem. 74, 93–126 (1978)

    Google Scholar 

  7. Gasteiger, J., Jochum, C., Marsili, M., Thoma, J.: Proceed. IVth Internat. Conf. on Computers in Chemical Research and Education, Novosibirsk, USSR 1978, p. 442–457

    Google Scholar 

  8. Gasteiger, J., Jochum, C., Marsili, M., Thoma, J.: Informal Commun. Math. Chem. 6, 177–199 (1979)

    Google Scholar 

  9. Gasteiger, J., Jochum, C., Marsili, M., Thoma, J.: Proceed. IVA-Symposium “The Use of Computers in Organic Chemistry”, Stockholm Sweden 1981, p. 51–68

    Google Scholar 

  10. Gasteiger, J., Marsili, M., Paulus, B.: in Data Processing in Chemistry, (Z. Hippe, Ed.) Elsevier, Amsterdam 1981, p. 229–246

    Google Scholar 

  11. Gasteiger, J.: Chim. Ind. (Milan) 64, 714–721 (1982)

    Google Scholar 

  12. Gasteiger, J., Christoph, B., Gann, L., Hutchings, M. G., Saller, H., Yuki, K.: Royal Soc. of Chem., Residential School “Computer-Aided Organic Synthesis Design and Molecular Graphics”, University of Leeds 1983

    Google Scholar 

  13. Marsili, M., Gasteiger, J., Carter, R. E.: Chimica Oggi, 1984, (9) 11–18

    Google Scholar 

  14. Dugundji, I., Ugi, I.: Topics Curr. Chem. 39, 19–64 (1973)

    Google Scholar 

  15. Ugi, I., Gillespie, P. D.: Angew. Chem. 83, 980–981; 982–985 (1971); Angew. Chem. Int. Ed. Engl. 10, 914, 915 (1971)

    Google Scholar 

  16. Hofmann, H. M. R. and Rabe, J.: Angew. Chem. 97, 96–112 (1985); Angew. Chem. Int. Edn. Engl. 24, 94–123 (1985)

    Google Scholar 

  17. Blair, J., Gasteiger, J., Gillespie, C., Gillespie, P. D., Ugi, I.: Tetrahedron 30, 1845–1859 (1974)

    Article  Google Scholar 

  18. Cahn, R. S., Ingold, C., Prelog, V.: Angew. Chem. 78, 413–447 (1966); Angew. Chem. Int. Ed. Engl. 5, 385–419 (1966)

    Google Scholar 

  19. Prelog, V., Helmchen, G.: Angew. Chem. 94, 614–631 (1982); Angew. Chem. Int. Ed. Engl. 21, 567–584 (1982)

    Google Scholar 

  20. Jochum, C., Gasteiger, J.: J. Chem. Inf. Comput. Sci., 17, 113–117 (1977); ibid. 19, 49–50 (1979)

    Article  Google Scholar 

  21. Christoph, B.: unpublished results

    Google Scholar 

  22. Gasteiger, J., Jochum, C.: J. Chem. Inf. Comput. Sci. 19, 43–48 (1979)

    Article  Google Scholar 

  23. Bart, J. C. J., Garagnani, E.: Z. Naturforsch. 31b, 1646–1653 (1976); ibid. 32b, 455–464 (1977); ibid. 32b, 465–468 (1977); ibid 32b, 678–683 (1977)

    Google Scholar 

  24. Huisgen, R.: Angew. Chem. 75, 604–637 (1963); ibid. 75, 742–754 (1963)

    Google Scholar 

  25. Alper, H., Perera, C. P., Ahmed, F. R.: J. Am. Chem. Soc. 103, 1289–1291 (1981)

    Article  Google Scholar 

  26. Skakibara, T., Alper, H.: J. Chem. Soc. Chem. Commun. 1979, 458

    Google Scholar 

  27. Suckling, C. J., Suckling, K. E., Suckling, C. W.: Chemistry Through Models, Cambridge University Press, Cambridge 1978

    Google Scholar 

  28. Eigen, M.: The Physicist's Conception of Nature, quoted in “A Dictionary of Contemporary Quotations”, compiled by Green, J., Pan Books 1982

    Google Scholar 

  29. Cox, J. D., Pilcher, G.: Thermochemistry of Organic and Organometallic Compounds, Academic Press, London 1970

    Google Scholar 

  30. Caglioti, E., Marsili, M.: results presented at 7th Internat. Conf. on Computers in Chemical Research and Education, Garmisch-Partenkirchen, W. Germany 1985

    Google Scholar 

  31. Gasteiger, J.: Comput. Chem. 2, 85–88 (1978)

    Google Scholar 

  32. Gasteiger, J.: Tetrahedron 35, 1419–1426 (1979)

    Google Scholar 

  33. Allen, T. L.: J. Chem. Phys. 31, 1039–1049 (1959)

    Google Scholar 

  34. Kalb, A. J., Chung, A. L. H., Allen, T. L.: J. Am. Chem. Soc. 88, 2938–2942 (1966)

    Google Scholar 

  35. Benson, S. W., Buss, J. H.: J. Chem. Phys. 29, 546–572 (1958)

    Google Scholar 

  36. Benson, S. W.: Thermochemical Kinetics, 2nd Ed. Wiley, New York 1976

    Google Scholar 

  37. Gasteiger, J., Jacob, P., Strauss, U.: Tetrahedron 35, 139–146 (1979)

    Google Scholar 

  38. Gann, L., Löw, P., Sello, G., Yuki, K.: unpublished results

    Google Scholar 

  39. Gasteiger, J., Dammer, O.: Tetrahedron 34, 2939–2945 (1978)

    Google Scholar 

  40. Guthrie, J. P., Cullimore, P. A.: Can. J. Chem. 57, 240–248 (1979)

    Google Scholar 

  41. Guthrie, J. P.: ibid. 57, 797–802 (1979)

    Google Scholar 

  42. Egger, K. W., Cocks, A. T.: Helv. Chim. Acta 56, 1516–1536 (1973)

    Google Scholar 

  43. McMillen, D. F., Golden, D. M.: Ann. Rev. Phys. Chem. 33, 493–532 (1982)

    Google Scholar 

  44. Chapman, N. B., Shorter, J.: Advances in Linear Free Energy Relationships, Plenum Press, London 1972

    Google Scholar 

  45. Chapman, N. B., Shorter, J.: Correlation Analysis in Chemistry — Recent Advances, Plenum Press New York 1978

    Google Scholar 

  46. Mulliken, R. S.: J. Chem. Phys. 23, 1833–1840 (1955)

    Article  Google Scholar 

  47. Mulliken, R. S.: ibid, 2, 782–793 (1934)

    Google Scholar 

  48. Hinze, J., Jaffe, H. H.: J. Am. Chem. Soc. 84, 540–546 (1962); J. Phys. Chem. 67, 1501–1506 (1963)

    Google Scholar 

  49. Hinze, J., Whitehead, M. A., Jaffe, H. H.: J. Am. Chem. Soc. 85, 148–154 (1963)

    Google Scholar 

  50. Sanderson, R. T.: Science 144, 670 (1964)

    Google Scholar 

  51. Huheey, J. E.: J. Phys. Chem. 69, 3284–3291 (1965); ibid. 70, 2086–2092 (1966)

    Google Scholar 

  52. Gasteiger, J., Marsili, M.: Tetrahedron Letters 1978, 3181–3184

    Google Scholar 

  53. Gasteiger, J., Marsili, M.: Tetrahedron 36, 3219–3228 (1980)

    Google Scholar 

  54. Guillen, M. D., Gasteiger, J.: ibid. 39, 1331–1335 (1983)

    Google Scholar 

  55. Mortier, W. J., Van Genechten, K., Gasteiger, J.: J. Am. Chem. Soc. 107, 829–835 (1985)

    Google Scholar 

  56. Gasteiger, J., Marsili, M.: Org. Magn. Resonance 15, 353–360 (1981)

    Google Scholar 

  57. Gasteiger, J., Guillen, M. D.: J. Chem. Res. (S) 1983, 304–305; (M) 1983, 2611–2624

    Google Scholar 

  58. Knorr, R., Saller, H., Gasteiger, J.: unpublished results

    Google Scholar 

  59. Marsili, M., Gasteiger, J.: Croat. Chem. Acta 53, 601–614 (1980)

    Google Scholar 

  60. Gasteiger, J., Saller, H.: Angew. Chem. 97, 699–701 (1985); Angew. Chem. Int. Ed. Engl. 24, 687–689 (1985)

    Google Scholar 

  61. Hutchings, M. G., Gasteiger, J.: Tetrahedron Lett. 24, 2541–2544 (1983)

    Google Scholar 

  62. Pauling, L.: The Nature of the Chemical Bond, 3rd Edit., Cornell University Press, Ithaca, N.Y. 1960, p. 88

    Google Scholar 

  63. Lias, S. G., Liebman, J. F., Levin, R. D.: J. Phys. Chem. Ref. Data 13, 695–808 (1984)

    Google Scholar 

  64. Saller, H.: Ph. D. thesis, TU München 1985

    Google Scholar 

  65. Gasteiger, J., Hutchings, M. G.: Tetrahedron Lett. 24, 2537–2540 (1983)

    Google Scholar 

  66. Gasteiger, J., Hutchings, M. G.: J. Chem. Soc. Perkin II, 1984, 559–564

    Google Scholar 

  67. Gasteiger, J., Löw, P.: unpublished results

    Google Scholar 

  68. Gasteiger, J., Hutchings, M. G.: J. Am. Chem. Soc. 106, 6489–6495 (1984)

    Google Scholar 

  69. Wolf, J. F., Abboud, J. L. M., Taft, R. W.: J. Org. Chem. 42, 3316–3317 (1977)

    Google Scholar 

  70. Bordwell, F. G., Drucker, G. E., McCollum, G. J.: ibid. 47, 2504–2510 (1982)

    Google Scholar 

  71. Hutchings, M. G., Gasteiger, J.: J. Chem. Soc. Perkin 2, 1986, in press

    Google Scholar 

  72. Hutchings, M. G., Gasteiger, J.: J. Chem. Soc. Perkin 2, 1986, in press

    Google Scholar 

  73. Kreevoy, M. M., Taft, R. W., J. Am. Chem. Soc. 77, 5590–5595 (1955)

    Google Scholar 

  74. Fukui, K.: Fortschr. Chem. Forsch. 15, 1–85 (1970); Acc. Chem. Res. 4, 57–64 (1971)

    Google Scholar 

  75. Houk, K. N.: Topics Curr. Chem. 79, 1–40 (1979)

    Google Scholar 

  76. Burnier, J. S., Jorgensen, W. C.: J. Org. Chem. 49, 3001–3020 (1984)

    Google Scholar 

  77. Gasteiger, J., Hutchings, M. G., Saller, H.: unpublished results

    Google Scholar 

  78. Saller, H., Löw, P., Hutchings, M. G., Gasteiger, J.: results presented at the 7th Internat. Conf. on Computers in Chemical Research and Education, Garmisch-Partenkirchen, W. Germany 1985

    Google Scholar 

  79. Gasteiger, J., Hutchings, M. G., Löw, P., Saller, H.: in: Artificial Intelligence Applications in Chemistry, ACS-Symposium Series, in press

    Google Scholar 

  80. Snowden, R. L.: Helv. Chim. Acta 66, 1031–1038 (1985)

    Google Scholar 

  81. Meinwald, J., Labana, S. S., Chadha, M. S.: J. Am. Chem. Soc. 85, 582–585 (1963)

    Google Scholar 

  82. Rey, M., Dreiding, A. S.: Helv. Chim. Acta 48, 1985–1987 (1965)

    Google Scholar 

  83. Baxter, A. D., Roberts, S. M., Scheinmann, F., Wakefield, B. J., Newton, R. F.: J. Chem. Soc., Chem. Commun. 1983, 932–933

    Google Scholar 

  84. Ho, T. L., Stark, C. J.: Liebigs Ann. Chem. 1983, 1446–1447

    Google Scholar 

  85. Piancatelli, G., Scettri, A., David, G., D'Auria, M.: Tetrahedron 34, 2775–2778 (1978)

    Google Scholar 

  86. Dohgane, I., Yamachika, H., Minai, M.: J. Synth. Org. Chem. (Japan) 1984, 896–903

    Google Scholar 

  87. Bertz, S. H.: J. Am. Chem. Soc. 103, 3599–3601 (1981); ibid. 104, 5801–5803 (1982)

    Google Scholar 

  88. Hiller, C., Christoph, B., Gann, L., Gasteiger, J.: results presented at 7th Internat. Conf. on Computers in Chemical Research and Education, Garmisch-Partenkirchen, W. Germany 1985

    Google Scholar 

  89. Michie, D., Johnston, R.: The Creative Computer, Pelican Books, England 1985

    Google Scholar 

Download references

Author information

Author notes

  1. Michael G. Hutchings

    Present address: Organics Division, Imperial Chemical Industries plc, Hexagon House, Blackley, M9 3DA, Manchester, England

  2. Mario Marsili

    Present address: Computer Chemistry Lab., CNR, Area della Ricerca, Monterotondo S., I-00016, Rome, Italy

  3. Kazumi Yuki

    Present address: Sumitomo Chemical Co. Ltd., Osaka, Japan

Authors and Affiliations

  1. Organisch-Chemisches Institut, Technische Universität München, D-8046, Garching, FRG

    Johann Gasteiger, Michael G. Hutchings, Bernd Christoph, Leopold Gann, Christian Hiller, Peter Löw, Mario Marsili, Heinz Saller & Kazumi Yuki

Authors
  1. Johann Gasteiger
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Michael G. Hutchings
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Bernd Christoph
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Leopold Gann
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Christian Hiller
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Peter Löw
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Mario Marsili
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Heinz Saller
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Kazumi Yuki
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 1987 Springer-Verlag

About this paper

Cite this paper

Gasteiger, J. et al. (1987). A new treatment of chemical reactivity: Development of EROS, an expert system for reaction prediction and synthesis design. In: Organic Synthesis, Reactions and Mechanisms. Topics in Current Chemistry, vol 137. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-16904-0_14

Download citation

  • DOI: https://doi.org/10.1007/3-540-16904-0_14

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-16904-8

  • Online ISBN: 978-3-540-47161-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation