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Title: Investigation of keto-enol tautomerism of doxycycline and other tetracyclines in aqueous solutions
Authors: Naidong, Weng ×
Sun, H
Roets, Eugene
Busson, Roger
Hoogmartens, Jos #
Issue Date: Jul-1993
Publisher: Elsevier science bv
Series Title: International journal of pharmaceutics vol:96 issue:1-3 pages:13-21
Abstract: The keto and enol tautomers of doxycycline were separated by liquid chromatography on poly(styrene-divinylbenzene). The keto-enol tautomerism occurred between C-11a and C-12. The chemical structure of the tautomers was elucidated by on-line and off-line UV spectrophotometry and by C-13-NMR spectrometry. The kinetics of the equilibrium were investigated in the pH range 1-12. The equilibrium was subject to base catalysis. The tautomerism was enhanced by protonation of doxycycline. The assignment of the groups responsible for the micro-ionization of doxycycline was discussed. Activation parameters were determined at pH 4.0.
ISSN: 0378-5173
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Pharmaceutical Analysis
Medicinal Chemistry (Rega Institute)
× corresponding author
# (joint) last author

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