NUCLEOPHILIC DISPLACEMENTS ON PHOSPHONIC ACID ESTERS.
Quarterly rept. no. 5, 1 Sep 65-30 Apr 66,
BROWN UNIV PROVIDENCE R I
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Data on the reaction of p-nitrophenyl methylphosphonate with a variety of hydroxamic acids is reported and discussed. Various experimental difficulties served to limit the number of successful trials. An attempt to obtain Bronsted plot for the observed data showed a small dependence upon the basicity of the hydroxamic acid. Consideration is also given to the reaction of p-nitrophenyl methylphosphonate with a series of tertiary amines. A Bronsted plot of amine pKa vs. log K2 second order rate constant has a slope of 0.31. It was also observed that only freshly distilled amines gave consistent rate data. A small rate enhancement was noted with an increase in ionic strength. Author
- Organic Chemistry