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The infrared absorption spectra of ring-D steroid lactones—I:Intense hydrogen bonding in estrololactone

Authors
Journal
Spectrochimica Acta
0371-1951
Publisher
Elsevier
Publication Date
Volume
13
Issue
3
Identifiers
DOI: 10.1016/0371-1951(58)80083-1
Disciplines
  • Physics

Abstract

Abstract It has been observed that an unusual tendency for hydrogen bonding occurred in the estrololactone molecule. Marked displacements of the hydroxyl vibrations from approximately 3500 to 3200 cm −1 and of the lactone carbonyl absorption from approximately 1740 to 1677 cm −1 took place. Comparison of the infrared spectra of other ring-D steroid lactones indicated that the hydrogen bonding was of an intermolecular nature and required the presence of the 3-hydroxyl attached to a benzenoid ring-A and a 17a-ketone carbonyl associated with a lactone unit in a homo ring-D. Alteration of these structural requirements restored the displaced maxima to higher frequencies.

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