Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Kinetics and Mechanism of the Hydrolysis of ${\alpha}$, N-Diphenylnitrone

  • Tae-Rin Kim (Department of Chemistry, Korea University) ;
  • Kwang-Il Lee (Department of Chemistry, Kyounggi University)
  • Published : 1991.06.20
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Abstract

The rate constants of hydrolysis of ${\alpha}$, N-diphenylnitrone and its derivatives have been determined by UV spectrophotometry from pH 2.0 to 13.5, and a rate equation which can be applied over a wide pH range was obtained. On the basis of rate equation, hydrolysis product, and general base and substituent effects, a plausible mechanism of hydrolysis has been proposed: Below pH 5, the hydrolysis was initiated by the protonation and followed by the addition of water to ${\alpha}$-carbon. However, above pH 11, the hydrolysis was proceeded by the addition of hydroxide ion to ${\alpha}$-carbon. In the range of pH 5-11, the addition of water to nitrone is rate controlling step.

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  1. Baker’s yeast (Saccharomyces cerevisiae) mediated transformations of C-aryl-N-phenylnitrones vol.47, pp.28, 2006, https://doi.org/10.1016/j.tetlet.2006.05.035
  2. The question of the regiodirection of the [2+3] cycloaddition reaction of triphenylnitrone to nitroethene vol.45, pp.6, 1991, https://doi.org/10.1007/s10593-009-0318-3