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The crystal and molecular structures of the diastereomeric (4Z)- and (4E)-3-oxo-2,3-dihydrobilatrienes-abc

Die Kristall- und Molekülstruktur zweier diastereomerer (4Z)- und (4E)-3-Oxo-2,3-dihydrobilatriene-abc

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

Abstract

The molecular and crystal structures of two diastereomeric 3-oxo-2,3-dihydrobilatrienes-abc1 and2 are determined at low (1, 2) and room temperature (2). The configurations at the exocyclic double bond in position 4 are found to be (Z) for1 and (E) for2. Tautomerism, conformation and crystal packing of1 and2 can be understood on the basis of the pattern of intra- and intermolecular hydrogen bonds. Compared to1, a more open helix conformation is found for the (E) diastereomer2. An analysis of crystallographically observed temperature factors of2 yields the result that the highest flexibility is found for the saturated lactam ring.

Zusammenfassung

Die Molekül- und Kristallstruktur zweier diastereomerer 3-Oxo-2,3-dihydrobilatriene-abc1 und2 wurde bei tiefer Temperatur (1, 2) und Raumtemperatur (2) bestimmt. Die Konfiguration an der exocyclischen Doppelbindung in Position 4 von1 wird als (Z), von2 als (E) gefunden. Tautomerie, Konformation und Kristallpackung werden auf Grund der intra- und intermolekularen Wasserstoffbrückenbindungen verständlich. Eine gegenüber1 aufgeweitete Helixkonformation wird für das (E)-Diastereomere2 gefunden. Aus einer Analyse der kristallographisch beobachteten Temperaturkoeffizienten von2 wird auf eine ausgeprägte Flexibilität des gesättigten Laktamringes geschlossen.

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Authors and Affiliations

  1. Institut für Physikalische Chemie, Universität Graz, A-8010, Graz, Austria

    Christoph Kratky

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

    Heinz Falk & Karl Grubmayr

Authors
  1. Christoph Kratky
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  2. Heinz Falk
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  3. Karl Grubmayr
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Herrn Prof.Josef Schurz zum 60. Geburtstag gewidmet.

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Kratky, C., Falk, H. & Grubmayr, K. The crystal and molecular structures of the diastereomeric (4Z)- and (4E)-3-oxo-2,3-dihydrobilatrienes-abc. Monatsh Chem 116, 745–760 (1985). https://doi.org/10.1007/BF00809153

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  • DOI: https://doi.org/10.1007/BF00809153

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