Kinetics of the reaction of N-Methylacetamide with hypobromous acid
Knox, Jane Levitas
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N-methylacetamide reacts with hypobromous acid to form N-bromo-N-methylacetamide and water. The kinetics of the reaction were studied spectrophotometrically using a Cary 14 spectrophotometer to observe the absorption of hypobromous acid at 3300 A. The reaction in aqueous solution is reversible under the mildly basic conditions at which it was studied and is of the type A + B --> C if water is disregarded since its concentration remains constant. Borate and carbonate buffers, pH 8.5-10.0, were used to keep the pH constant. An analysis of the kinetic data showed that the undissociated hypobromous acid reacts with N-methylacetamide in a second order reaction. Extinction coefficients of hypobromous acid were determined using concentrations known from iodometric titrations. The values increase with pH from 111 liters/mole at pH 8.5 to 265 liters/mole at pH 10 in borate buffers at 26.5°C. Extinction coefficients of N-bromo-N-methylacetamide were determined by forcing the reaction to completion using excess N-methylacetamide which does not absorb at 3300 A. Values of 24-26 liters/mole in borate buffers at 26.5°C were found. Extinction coefficients in carbonate buffer are of the same order of magnitude. [TRUNCATED]
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