#### Date of Award

8-1982

#### Degree Name

Doctor of Philosophy

#### Department

Chemistry

#### First Advisor

Dr. D.C. Berndt

#### Second Advisor

Dr. R.H. Anderson

#### Third Advisor

Dr. R.C. Nagler

#### Fourth Advisor

Dr. R.C. Eisenberg

#### Abstract

The rate constants for hydrolysis of ten derivatives of benzohydroxamic acid, namely, p-H, p-CH(,3), m-CH(,3), p-CH(,3)CH(,2), p-OCH(,3), p-NO(,2), p-Cl, and m-Cl, in 0.160 and 0.158 M HCl at 67.9-68.2(DEGREES)C without and with sodium 1-dodecanesulfonate were determined. There is a good linear correlation between log k(,w) and the Hammett substituent constants, (sigma), for all para and meta derivatives where k(,w) is the rate constant in the bulk aqeous phase. In the presence of micelles all the compounds, except the meta-nitro derivative, followed the standard pseudophase model of micellar catalysis. However, correlations of log k(,m) or log K/N, where k(,m) is the rate constant in the micellar phase, K is the substrate-micelle association constant and N is the micellar aggregation number, do not exist for the para and meta compounds considered as a group. Only para derivatives alone gave the meaningful results. A multiple regression analysis indicates that log k(,m) is very well correlated by a combination of the lipophilicity substituent parameter, (pi), and the polar substituent parameter, (sigma)('+). Log K/N is correlated roughly with the (pi) and (sigma)('+) parameters. The results indicate that specific micellar effects on the reaction rates occur for the systems investigated.

#### Access Setting

Dissertation-Open Access

#### Recommended Citation

Utrapiromsuk, Nop, "Micellarly Catalyzed Reaction of Substituted Benzohydroxamic Acids" (1982). *Dissertations*. 2535.

https://scholarworks.wmich.edu/dissertations/2535