A spectroscopic study of the bromination of the endocrine disruptor ethynylestradiol.
Bromination of ethynylestradiol (EE2) was studied using fluorescence and conventional and stopped-flow absorbance spectroscopy. EE2 transformations in the presence of bromine were determined to proceed through sequential reactions. The first step is very rapid and results in the formation of a brominated cyclohexadienone that is susceptible to reduction but in oxidative conditions it undergoes a transformation into monobromo-EE2 in a first-order OH- -accelerated reaction. The transformation from monobromo-EE2 to dibromo-EE2 follows a similar mechanism. The rates of reactions of bromine-substituted EE2 species are orders of magnitude lower than that of the parent compound indicating that these species can persist in conditions typical for water treatment operations.
Lu
Junhe
J
Department of Crop and Soil Sciences, University of Georgia, Griffin, GA 30223, United States.
Korshin
Gregory V
GV
D052244:Endocrine Disruptors / Q000737:chemistry*; D004997:Ethinyl Estradiol / Q000737:chemistry*; D054879:Halogenation; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D015394:Molecular Structure; D013050:Spectrometry, Fluorescence
D052244:Endocrine Disruptors; D004997:Ethinyl Estradiol