Monatshefte für Chemie / Chemical Monthly

, Volume 112, Issue 11, pp 1325–1332 | Cite as

Beiträge zur Chemie der Pyrrolpigmente, 42. Mitt. Kraftfeldrechnungen an Gallenfarbstoffen: Die Energiehyperfläche rubinoider Pigmente

  • Heinz Falk
  • Norbert Müller
Organic Chemistry and Biochemistry

On the chemistry of pyrrole pigments, XLII: Force field calculations on bile pigments: The energy hypersurface of rubinoid pigments


The energy hypersurface of rubinoid bile pigments is calculated using a force field model previously described. Two cases are observed. I: The pigment is substituted symmetrically or unsymmetrically by apolar groups. This results in a very shallow energy valley containing several enantiomeric conformers of approximately equal energies. II: Substitution by polar groups, especially in position 8 and 12 of the rubin skeleton, (e.g.−CH2−CH2−COOH) is followed by a “lock in” bonding between such groups and the lactam ring functions. Thereby only two enantiomeric conformers, which are energetically stabilized, are possible. The barrier between these species amounts to about 40 kJ/mol. These results are compared with the experimental facts available so far. An analysis of the corresponding energy hypersurfaces of the diastereomeric forms of (Z,Z)-, (E,Z)-, (Z,E)- and (E,E)-configurations is given as well.


Bilirubin Conformational analysis Force field calculations 


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Copyright information

© Springer-Verlag 1981

Authors and Affiliations

  • Heinz Falk
    • 1
  • Norbert Müller
    • 1
  1. 1.Institut für Analytische, Organische und Physikalische ChemieJohannes-Kepler-Universität LinzLinzÖsterreich

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