Effects of amine nature and nonleaving group substituents on rate and mechanism in aminolyses of 2,4-dinitrophenyl X-substituted benzoates.

@article{Um2004EffectsOA,
  title={Effects of amine nature and nonleaving group substituents on rate and mechanism in aminolyses of 2,4-dinitrophenyl X-substituted benzoates.},
  author={I. Um and K. Kim and Hye-Ran Park and M. Fujio and Y. Tsuno},
  journal={The Journal of organic chemistry},
  year={2004},
  volume={69 11},
  pages={
          3937-42
        }
}
  • I. Um, K. Kim, +2 authors Y. Tsuno
  • Published 2004
  • Chemistry, Medicine
  • The Journal of organic chemistry
Second-order rate constants have been measured for the reactions of 2,4-dinitrophenyl X-substituted benzoates (1a-f) with a series of primary amines in 80 mol % H(2)O/20 mol % DMSO at 25.0 +/- 0.1 degrees C. The Brønsted-type plot for the reactions of 1d with primary amines is biphasic with slopes beta(1) = 0.36 at the high pK(a) region and beta(2) = 0.78 at the low pK(a) region and the curvature center at pK(a) degrees = 9.2, indicating that the reaction proceeds through an addition… Expand
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