The Description of Molecular Structure

  • I. Ugi
  • J. Dugundij
  • R. Kopp
  • D. Marquarding
Part of the Lecture Notes in Chemistry book series (LNC, volume 36)


The classical description of molecules is based on their empirical formula, constitution, configuration, and conformation. In this chapter, we shall briefly review these concepts and also that of chirality, as they are commonly understood. A discussion of some structural features of flexible molecules indicates that purely geometrically based concepts of configuration, conformation, and chirality so well as some currently used modifications of those concepts cannot be universally applied in a consistent manner. We then propose a unified conceptual framework for stereochemistry, including new definitions of stereoisomerism and chirality. These definitions are based on chemistry, rather than on geometric models, and have an unambiguous meaning for all molecules.


Observation Condition Rigid Model Flexible Molecule Asymmetric Carbon Atom Intramolecular Motion 
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  1. [1]
    J. Gasteiger, P. D. Gillespie, D. Marquarding and I. Ugi, Top, Curr. Chem. 48, 1 (1974).CrossRefGoogle Scholar
  2. [2]
    J. Dugundji and I. Ugi, Top. Curr. Chem. 39, 19 (1973).Google Scholar
  3. [3]
    I. Ugi, J. Bauer, J. Brandt, F. Friedrich, J. Gasteiger, C. Jochum and W. Schubert, Angew. Chem. 91, 99 (1979), Angew. Chem. Int. Ed. 18, 111 (1979), I. Ugi, J. Bauer, J. Brandt, J. Friedrich, J. Gasteiger, C. Jochum, W. Schubert and J. Dugundji, ins “Computational Methods in Chemistry”, ed.: J. Bargon, Plenum Press, New York, N. Y. 1980, p. 275; I. Ugi, J. Bauer, J. Brandt, J. Dugundji, R. Frank, J. Friedrich, A. v. Scholley and W. Schubert, in: “Data Processing in Chemistry”, ed: Z. Hippe, PWN-Polish Sc-Pub. Warsaw 1981, p. 219; J. Brandt, J. Bauer, R. M. Frank and A. v. Scholley, Chem. Scripta 18, 53 (1981); C. Jochum, J. Gasteiger, I. Ugi and J. Dugundji, Z. Naturforsch. 37B, 1205 (1982); J. Bauer and I. Ugi, J. Chem. Res. 1982(S) 298, (M) 310, 3201.CrossRefGoogle Scholar
  4. [4]
    J. H. van’t Hoff, Arch. Neer. Sci. Exactes Natur. 9, 445 (1874); Bull. Soc. Chim. France [2] 23, 295 (1875); “The Arrangement of Atoms in Space”, Longmans Green, London 1898.Google Scholar
  5. [5]
    J. A. LeBel, Bull. Soc. Chim. France [2] 22, 337 (1874).Google Scholar
  6. [6]
    J. Weyer, Angew. Chem. 86, 604 (1974); Angew. Chem. Int. Ed. 12, 591 (1974); J. K. O’Loane, Chem. Rev. 80, 41 (1980).CrossRefGoogle Scholar
  7. [7]
    I. Ugi, D. Marquarding, H. Klusacek, G. Gokel and P. Gillespie, Angew. Chem. 82, 741 (1970); Angew. Chem. Int. Ed. 9, 703 (1970).CrossRefGoogle Scholar
  8. [8]
    E. L. Eliel, “Stereochemistry of Carbon Compounds”, McGraw-Hill, New York 1962; K. Mislow, “Introduction to Stereochemistry”, Benjamin, New York 1965; J. F. Stoddart, in “Comprehensive Organic Chemistry”, Vol. 1, eds.: Sir D. H. R. Barton and W. D. Ollis, Pergamon Press, Oxford 1979, p. 13; see also: W. Bähr and H. Theobald, “Organische Stereochemie-Begriffe und Definitionen”, Springer-Verlag, Heidelberg, 1973, p. 107; B. Testa, “Principles of Organic Stereochemistry”, Marcel Dekker, New York 1979; idem, “Grundlagen der Organischen Stereochemie”, Verlag Chemie, Weinheim 1983.Google Scholar
  9. [9]
    Lord Kelvin, “Baltimore Lectures”, Clay and Sons, London 1904, p. 436, 619.Google Scholar
  10. [10]
    J. Dugundji, R. Kopp, D. Marquarding and I. Ugi, Top. Curr. Chem. 75, 165 (1978).CrossRefGoogle Scholar
  11. [11]
    K. Mislow and P. Bickart, Isr. J. Chem. 15, 1 (1977); E. L. Eliel, ibid. 15, 7 (1977); R. G. Woolley, J. Amer. Chem. Soc. 100, 1073 (1978).Google Scholar
  12. [12]
    E. L. Eliel, N. L. Allinger, S. J. Angyal and G. A. Morrison, “Conformational Analysis”, Interscience, New York 1965; M. Hanack, “Conformation Theory”, Academic Press, New York 1965; G. Chiurdoglu, ed., “Conformational Analysis”, New York 1971; J. Dale, “Stereochemie und Konformationsanalyse”, Verlag Chemie, Weinheim 1979.Google Scholar
  13. [13]
    C. E. Wintner, “Strands of Organic Chemistry”, Holden-Day, San Francisco 1979, p. 9.Google Scholar
  14. [14]
    W. v. E. Doering and W. R. Roth, Angew. Chem. 75, Zl (1963); Angew. Chem. Int. Ed. Engl. 2, 24 (1963); G. Schröder, ibid. 75, 722 (1963); 2, 694 (1963); J. F. M. Oth, R. Merenyi, G. Engel and G. Schröder, Tet. Lett. 1966, 3377; J. F. M. ah, R. Merenyi, H. Röttele and G. Schröder, Chem. Ber. 100, 3538 (1967).CrossRefGoogle Scholar
  15. [15]
    J. E. Leonard, G. S. Hammond and H. E. Simmons, J. Amer. Chem. Soc. 97, 5052 (1975); see also: ref. [7,16].CrossRefGoogle Scholar
  16. [16]
    P. Gillespie, P. Hoffmann, H. Klusacek, D. Marquarding, S. Pfohl, F. Ramirez, E. A. Tsolis and I. Ugi, Angew. Chem. 83, 691 (1971); Angew. Chem. Int. Ed. 10, 687 (1971).CrossRefGoogle Scholar
  17. [17]
    V. Prelog, in: “Perspectives in Organic Chemistry”, ed.: Sir A. Todd, Interscience, New York 1956.Google Scholar
  18. [18]
    I. Ugi, in: “Jahrbuch 1964 der Akademie der Wissenschaften in Güttingen”, Vandenhoek & Rupprecht, Göttingen 1965, p. 21.Google Scholar
  19. [19]
    A. Streitwieser and C. H. Heathcock, “Introduction to Organic Chemistry”, Mc Millan, New York 1981, p. 83.Google Scholar
  20. [20]
    see e.g.: N. Trong Anh and O. Eisenstein, Tet. Lett. 1976, 155.Google Scholar
  21. [21]
    K. Mislow, Science 120, 232 (1954); Trans N. Y. Acad. Sei. 19, 298 (1957).CrossRefGoogle Scholar
  22. [22]
    D. J. Cram and F. A. Abd Elhafez, J. Amer. Chem. Soc. 74., 5828, 5851 (1952); see also: D. Krug er, A. E. Sophitz and C. A. Kingsbury, J. Org. Chem. 49, 778 (1984); J. Mulzer, Nachr. Chem. Tech. 32, 17 (1984) and references therein.CrossRefGoogle Scholar
  23. [23]
    V. Prelog, Helv. Chim. Acta 36, 308 (1953).CrossRefGoogle Scholar
  24. [24]
    J. D. Morrison and H. S. Mosher, “Asymmetric Organic Reactions”, Prentice-Hall, Englewood Cliffs, N.J. 1971.Google Scholar
  25. [25]
    I. Ugi, Z. Naturforsch. 20B, 405 (1965).Google Scholar
  26. [26]
    E. Ruch and I. Ugi, Iheoret. Chim. Acta (Berl.) 4, 287 (1966); Top. Stereochem. 4, 99 (1969).Google Scholar
  27. [27]
    V. Prelog (Nobel Lecture), Science 193, 17 (1976); see also: E. F. Meyer, J. Comput. Chem. 1, 229 (1980); V. Prelog and G. Helmchen, Angew. Chem. 94, 614 (1982); Angew. Chem. Int Ed. 21, 567 (1982).Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1984

Authors and Affiliations

  • I. Ugi
    • 1
  • J. Dugundij
    • 2
  • R. Kopp
    • 1
  • D. Marquarding
    • 1
  1. 1.Organisch-Chemisches InstitutTechnischen Universität MünchenGarchingDeutschland
  2. 2.Department of MathematicsUniversity of Southern CaliforniaLos AngelesUSA

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