5,5-Dimethyl-2-pyrrolidone-N-oxyl formation in electron spin resonance studies of electrolyzed NaCl solution using 5,5-dimethyl-1-pyrroline-N-oxide as a spin trapping agent.
Electrolyzed oxidizing (EO) water has recently generated much interest as a disinfectant in the food industry. 5,5-Dimethyl-1-pyrroline-N-oxide (DMPO) is a spin trapping agent widely used in the electron spin resonance (ESR) characterization of oxygen-centered free radicals. The reaction between electrolyzed water, collected from the anode side of a two-chamber electrolyzer, and DMPO was investigated by ESR spectroscopy. Addition of DMPO to EO water generated an ESR spectrum identical to that of 5,5-dimethyl-2-pyrrolidone-N-oxyl (DMPOX), suggesting that a compound from EO water oxidized DMPO with the formation of DMPOX. To further investigate the electrolytically generated compound that oxidized DMPO, aqueous solutions of different sodium salts (sodium chloride, sodium citrate, and sodium iodide) with similar conductivities were electrolyzed. The DMPOX signal was not detected in the electrolyzed sodium citrate sample, suggesting that DMPOX formation in the electrolyzed NaCl sample might be due to an electrolytically generated chlorine species. A low DMPOX signal was also observed from the electrolyzed NaI sample, suggesting that a similar species obtained through the electrolysis of I- can also oxidize DMPO. Hypochlorous acid is proposed to oxidize the spin trap DMPO with the formation of DMPOX. In a neutral pH environment, electrolyzed water also oxidized DMPO to DMPOX. This is consistent with the DMPOX formation in the reaction of chlorine water (containing HOCl and Cl2) or sodium hypochlorite with DMPO.
Stan
Silvia D
SD
Department of Food Science and Technology, Oregon State University, 100 Wiegand Hall, Corvallis, Oregon 97331, USA.
Daeschel
Mark A
MA
D003497:Cyclic N-Oxides / Q000737:chemistry*; D004202:Disinfectants; D004578:Electron Spin Resonance Spectroscopy; D006861:Hydrogen Peroxide / Q000737:chemistry; D010084:Oxidation-Reduction; D012965:Sodium Chloride / Q000737:chemistry*; D013113:Spin Labels
C025634:5,5-dimethylpyrrolidin-2-one-1-oxide; D003497:Cyclic N-Oxides; D004202:Disinfectants; D013113:Spin Labels; C118085:superoxidized water; D012965:Sodium Chloride; C017245:5,5-dimethyl-1-pyrroline-1-oxide; D006861:Hydrogen Peroxide