Date of Award

1975

Document Type

Thesis

Degree Name

Master of Science (M.S.)

Department

Graduate School

First Advisor

Michael J. Minch

First Committee Member

Donald K. Wedegaertner

Second Committee Member

Paul H. Gross

Abstract

A general synthetic method for the synthesis of a new class of chiral surfactants with reactive OH groups was investigated. The surfactarits were made by quaternizing the corresponding tertiary amine, in isopropyl alcohol. These surfactants with -OH groups may form tightly-packed non-spherical micelles in the presence of WaOH or alkylamine and these .micelles, just like enzyme catalysts, may serve as stereoselective templates. In order to evaluate this stereospecificity, a kinetic study of the reactivity of several chi~al reactants in the presence of these micelles, was initiated. The first-order rate constant K for 4- nitrostyrene formation from p-nitrophenethyl trimethylammonium iodide in 0.1 M NaOH at 39°C, increased as a function of surfactant concentration Cs in a manner suggesting micellar catalysis. The data show that N-methyl Ndodecyl 3-hydroxy-piperidinium bromide (DPBr) is a better catalyst than N,N-dimethyl-N-[2-hydroxyethyTI N-hexadecylammonium bromide (CTOH) in the E2 elimination, probably because it is more hydrophobic. This high activity suggests that chiral surfactants may induce chirality.

Pages

103

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