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Zum Phänomen der induzierten optischen Aktivität: Der induzierte Circulardichroismus in Mischungsreihen

On the phenomenon of induced optical activity. The induced circular dichroism in mixtures

  • Organische Chemie Und Biochemie
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Abstract

The induced circular dichroism (ICD) of 4-Nitroso-N,N-dimethylaniline in a series of mixtures of CCl4, lactic and tartaric acid methylesters andcis-pinane, resp., was determined. From the dependence of the ICD on the concentration of chiral components the existence of a strong intermolecular interaction can be deduced—even in the case of apolarcis-pinane. Obviously the border line between associate induced CD (AICD) and dispersion induced CD (DICD) cannot be drawn unequivocally by experiment. The general phenomenology together with mechanistic models of ICD are discussed. It is proposed to use the term ICD exclusively, instead of others like AICD and DICD, which are only applicable when the predominant mechanism can be derived from experimental data. The term SICD (solvent induced CD) should be avoided for similar reasons.

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Literatur

  1. Blout E. R., Stryer L., Proc. Natl. Acad. Sci. U.S.45, 159 (1959);Bosnich B., J. Amer. Chem. Soc.88, 2606 (1966);89, 6143 (1967);Bosnich B., Harrowfield J. M., J. Amer. Chem. Soc.93, 4086 (1971).

    Google Scholar 

  2. Hayward L. D.,Totty R. N., Chem. Commun.1969, 676.

  3. Axelrod E.,Barth G.,Bunnenberg D., Tetrahedron Lett.1969, 5031.

  4. Blauer G., Structure and Bonding18, 69 (1974).

    Google Scholar 

  5. Bolard J., J. Chim. Phys.66, 389 (1969);67, 550 (1970).

    Google Scholar 

  6. Majumdar R. N., Carlini C., Nocci R., Ciardelli F., Schulz R. C., Makromol. Chem.117, 3619 (1976).

    Google Scholar 

  7. Harata K., Bioorganic Chemistry10, 255 (1981).

    Google Scholar 

  8. Shimizu H., Kaito A., Hatano M., Bull. Chem. Soc. Jap.52, 2678 (1979);54, 513 (1981).

    Google Scholar 

  9. Shimizu H., Kaito A., Hatano M., J. Amer. Chem. Soc.104, 7059 (1982).

    Google Scholar 

  10. Ito T., Zama M., Amagasa J., Biopolymers11, 1583 (1972).

    Google Scholar 

  11. Imae T., Ikeda S., Biopolymers14, 1213 (1975).

    Google Scholar 

  12. Kamiya M., Biochim. Biophys. A.562, 70 (1979).

    Google Scholar 

  13. Chen G. C., Krieger M., Kane J. P., Wu C. C., Brown M. S., Goldstein J. L., Biochem.19, 4706 (1980).

    Google Scholar 

  14. Klein H., Tetrahedron Lett.1979, 3835.

  15. Noack K., Helv. Chim. A.52, 2501 (1969).

    Google Scholar 

  16. Nordén B., Chemica Scripta7, 14 (1975).

    Google Scholar 

  17. Sherrington D. C.,Solaro R.,Chiellini E., J. Chem. Soc., Chem. Commun.1982, 1103.

  18. Takenaka S.,Kondo K.,Tokura N., J. Chem. Soc., Perkin II,1974, 1749;1975, 1520.

  19. Lee C. H., Chang C., Wetmur J. G., Biopolymers12, 1099 (1973).

    Google Scholar 

  20. Towell J. F., Woody R. W., Biochem.19, 4231 (1980).

    Google Scholar 

  21. Hayward L. D., Totty R. N., Can. J. Chem.49, 624 (1971).

    Google Scholar 

  22. Claesson S., Hayward L. D., Chem. Phys. Lett.20, 85 (1973).

    Google Scholar 

  23. Hayward L. D., Claesson S., Chem. Scripta9, 21 (1976).

    Google Scholar 

  24. Craig D. P., Power E. A., Thirunamachandran, Proc. R. Soc. London A348, 19 (1976); Chem. Phys. Lett.27, 149 (1974).

    Google Scholar 

  25. Frank-Kamenetskii M. D., Lukashin A. V., Optics and Spectroscopy30, 585 (1971).

    Google Scholar 

  26. Mason S. F., Chem. Phys. Lett.32, 201 (1975).

    Google Scholar 

  27. Nordén B., Chem. Scripta8, 20 (1975).

    Google Scholar 

  28. Nordén B., Schipper P. E., Chem. Scripta12, 72 (1977).

    Google Scholar 

  29. Hayward D. L., Chem. Phys. Lett.33, 53 (1975).

    Google Scholar 

  30. Schipper P. E., Inorg. Chim. Acta14, 161 (1975); Mol. Physics29, 1705 (1975).

    Google Scholar 

  31. Schipper P. E., Chem. Phys. Lett.30, 323 (1975).

    Google Scholar 

  32. Schipper P. E., Chem. Phys.12, 15 (1976).

    Google Scholar 

  33. Schipper P. E., Chem. Phys.23, 159 (1977).

    Google Scholar 

  34. Schipper P. E., Nordén B., Chem. Phys. Lett.67, 99 (1979).

    Google Scholar 

  35. Schipper P. E., Chem. Phys.57, 105 (1981).

    Google Scholar 

  36. Siehe z. B. die Untersuchungen vonCoulombeau C.,Rassat A., Bull. Soc. Chim. France1963, 2773;1966, 2752.

  37. Z. B.Hayward L. D., Stud. Phys. Theor. Chem.7, 169 (1969).

    Google Scholar 

  38. Tachibana T., Kurihara K., Naturwiss.63, 532 (1976).

    Google Scholar 

  39. Perrin J. H.,Wilsey M., Chem. Commun.1971, 769.

  40. Perrin J. H., Idsvoog P., J. Pharm. Sci.,59, 1525 (1970).

    Google Scholar 

  41. Siehe dazu das Modell vonSchipper P. E., Harrowell P. R., J. Amer. Chem. Soc.105, 723 (1983).

    Google Scholar 

  42. Kirschner S., Rec. Chem. Progr.32, 29 (1971).

    Google Scholar 

  43. Mason S. F.,Peackock R. D., Chem. Commun.1973, 712.

  44. Elliot Charney, The Molecular Basis of Optical Activity. New York: Wiley. 1979.

    Google Scholar 

  45. Schipper P. E., J. Amer. Chem. Soc.98, 7938 (1976).

    Google Scholar 

  46. Falk H., in: Bilirubin, Bile Pigments and Jaundice (Ostrow D., Hrsg.). New York: Marcel Dekker. 1984, im Druck.

    Google Scholar 

  47. Nitsche K., Suppan P., Chimia36, 346 (1982).

    Google Scholar 

  48. LeFevre R. J. W., Smith J. W., J. Chem. Soc.141, 2239 (1932).

    Google Scholar 

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Falk, H., Jungwirth, W. & Müller, N. Zum Phänomen der induzierten optischen Aktivität: Der induzierte Circulardichroismus in Mischungsreihen. Monatsh Chem 115, 455–466 (1984). https://doi.org/10.1007/BF00810007

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  • DOI: https://doi.org/10.1007/BF00810007

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