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Beiträge zur Chemie der Pyrrolpigmente, 53. Mitt.

On the chemistry of pyrrole pigments, LIII: Phytochrome model studies: The acid-base equilibrium of diastereomeric 2,3-dihydrobilatrienes-abc

Phytochrommodellstudien: Das Säure-Basen-Gleichgewicht diastereomerer 2,3-Dihydrobilatriene-abc

  • Organische Chemie Und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

ThepK a -value corresponding to the deprotonation of (4Z, 9Z, 15E)-2,3-dihydrobilatriene-abc was measured to be 13.6±0.1 using a stopped flow equipment. This represents a 50-fold decrease in acidity compared to the corresponding all-(Z) diastereomer. Also the pyrromethene type basicity of the (Z,Z,E) diastereomer is decreased by a factor of ten. By applying aFörster cycle a fundamental difference between the two diastereomers is revealed: Only the all-(Z) diastereomer exhibits a cross over of relative acidity and basicity on moving from ground to excited state.

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Literatur

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Authors and Affiliations

  1. Institut für Analytische, Organische und Physikalische Chemie, Johannes-Kepler-Universität Linz, A-4040, Linz, Österreich

    Heinz Falk & Ulrich Zrunek

  2. Institut für Theoretische Chemie und Strahlenchemie, Universität Wien, A-1090, Wien, Österreich

    Peter Wolschann

Authors
  1. Heinz Falk
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  2. Peter Wolschann
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  3. Ulrich Zrunek
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Falk, H., Wolschann, P. & Zrunek, U. Beiträge zur Chemie der Pyrrolpigmente, 53. Mitt.. Monatsh Chem 115, 243–249 (1984). https://doi.org/10.1007/BF00798415

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  • DOI: https://doi.org/10.1007/BF00798415

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