Campus Access Only

All rights reserved. This publication is intended for use solely by faculty, students, and staff of University of the Pacific. No part of this publication may be reproduced, distributed, or transmitted in any form or by any means, now known or later developed, including but not limited to photocopying, recording, or other electronic or mechanical methods, without the prior written permission of the author or the publisher.

Date of Award

1992

Document Type

Thesis - Pacific Access Restricted

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

To access this thesis/dissertation you must have a valid pacific.edu email address and log-in to Scholarly Commons.

Find in PacificSearch

Share

COinS

If you are the author and would like to grant permission to make your work openly accessible, please email