Newer Applications of Circular Dichroism in Natural Products Chemistry

  • R. C. Cambie
  • P. C. Ho
  • K. Netzke
  • W. Schoenfelder
  • F. Snatzke
  • G. Snatzke
  • J. Schulte
Conference paper

Abstract

Optical activity of a substance leads at least to three spectroscopic phenomena which are, however, related: Optical Rotatory Dispersion (ORD), i.e. the rotation of the plane of linearly polarized light by traversing the substance, Circular Dichroism, expressed as Δε ≡ εL - εR (if the relative molar mass of the molecules is known, or - in case of biopolymers - the mean residual relative molar mass), and Molar Ellipticity, [Θ] = 3300 × Δε. A necessary condition for optical activity of a substance is the Chirality of its molecules, i.e. the property of being not superposable onto its mirror image. This allows still the presence of (proper) axes of rotation Cp, but not improper ones (Sp, including S1 ≡ mirror plane, and S2 ≡ centre of inversion). Theoretically, the area under a CD-band is given by the scalar (or dot) product of the electric times the magnetic transition moments associated with the transition and this value is proportional to the Rotational strength
$$\text{R}_{\text{0i}} = 22.97 \times 10^{ - 40} \int {\left( {{{\Delta \varepsilon } \mathord{\left/ {\vphantom {{\Delta \varepsilon } \lambda }} \right.} \lambda }} \right)\text{d}\lambda } = \mu _{0\text{i}} \times \text{m}_{\text{i0}} \times \cos \left( \varphi \right)$$
(1)
(φ is the angle between the two transition moments, index 0 refers to the ground, and i to the excited state). Thus the CD is positive if is acute (including parallel moments), and negative if this angle is oblique (including antiparallel moments). R0i. has been defined in analogy to the Dipol Strength D0i, given by
$$\text{D}_{\text{0i}} = 91.88\; \times \;10^{ - 38} \int {\left( {{\varepsilon \mathord{\left/ {\vphantom {\varepsilon \lambda }} \right.} \lambda }} \right)\text{d}} \lambda = \mu _{0\text{i}}^2$$
(2)

Keywords

Ethyl Benzene Tyrosine Glycol Alkaloid 

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Copyright information

© Springer-Verlag Berlin Heidelberg 1988

Authors and Affiliations

  • R. C. Cambie
    • 2
  • P. C. Ho
    • 1
  • K. Netzke
    • 1
  • W. Schoenfelder
    • 1
  • F. Snatzke
    • 1
  • G. Snatzke
    • 1
  • J. Schulte
    • 1
  1. 1.Lehrstuhl für StrukturchemieUniversität BochumBochum 1Germany
  2. 2.Department of ChemistryUniversity of AucklandAucklandNew Zealand

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