Date of Award

Summer 1993

Document Type


Degree Name

Master of Science (MS)


Chemistry & Biochemistry



Committee Director

Frank E. Scully, Jr.

Committee Member

Charles E. Bell

Committee Member

Mark S. Elliott

Call Number for Print

Special Collections LD4331.C45W56


Model solutions of the amino acid methionine were chlorinated to seven chlorine-to-nitrogen (Cl2/N) molar ratios. After 30 minutes, the solutions were analyzed by high performance liquid chromatography (HPLC). At a Cl2/N molar ratio of 1, methionine sulfoxide was found to be the main product. At Cl2/N molar ratios ≥ 2, a mixture of methionine sulfoxide, methionine sulfone, an unidentified sulfoxide (product 1), and N-chloro-3-(methylsulfonyl) propionaldimine are formed. These products were identified by comparison to synthesized standards which were characterized by 1H-NMR and 13C-NMR nuclear magnetic resonance spectroscopy, ion trap mass spectroscopy, and infrared spectroscopy.

Methionine was quantitated in a primary municipal wastewater (TKN = 21.09 mg/L; [NH3] = 18.50 mg/L), and the distribution of chlorination products determined with the aid of a radiotracer (3H-methionine). These products were found to be similar to those found in model solutions. A scheme for the formation of chlorinated products of methionine is proposed.


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