Accession Number:

AD0667397

Title:

SUBSTITUENT EFFECTS IN HYDROXAMATE NUCLEOPHILE DISPLACEMENTS AT CARBONYL CENTERS.

Descriptive Note:

Final rept.,

Corporate Author:

DELAWARE UNIV NEWARK DEPT OF CHEMISTRY

Personal Author(s):

Report Date:

1967-08-31

Pagination or Media Count:

26.0

Abstract:

The charge effect previously discussed for nucleophilic displacements on isopropyl methylphosphonofluoridate by non-alpha but not by alpha nucleophiles was investigated in analogous reactions occurring at carbonyl centers. The catalytic coefficients determined for a variety of neutral and cationic para substituted benzohydroxamates in reaction with both p-nitrophenylbenzoate and p-nitrophenyl-p-nitrobenzoate were plotted in both Bronsted and Hammett linear free energy relationships. These and other data appear to be consistent with the conclusion that the charge effect is a reflection of the differences in the mechanism of charge dispersal in the respective transition states for alpha and non-alpha nucleophiles engaged in nucleophilic attack at unsaturated centers. Author

Subject Categories:

  • Organic Chemistry
  • Physical Chemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE