Kinetics and mechanism of the cyclization of omega-(p-nitrophenyl)-hydantoic acid amides: steric hindrance to proton transfer causes a 10(4)-fold change in rate.

@article{Angelova2003KineticsAM,
  title={Kinetics and mechanism of the cyclization of omega-(p-nitrophenyl)-hydantoic acid amides: steric hindrance to proton transfer causes a 10(4)-fold change in rate.},
  author={Violina T. Angelova and Anthony J. Kirby and Asen H Koedjikov and Ivan G. Pojarlieff},
  journal={Organic & biomolecular chemistry},
  year={2003},
  volume={1 5},
  pages={859-65}
}
The pH-rate profiles for the cyclization of primary 2,3-dimethyl and 2,2,3-trimethyl-hydantoinamides (2-UAm and 3-UAm respectively) differ strikingly from those for the cyclizations of the corresponding N-methylated amides 2-MUAm and 3-MUAm; which are dominated by the water reaction, spanning some 6 pH units. For the cyclization of UAm the plateau extends… CONTINUE READING