Citation
Sukenik, Chaim N. (1976) Catalysis of Organic Reactions: Part I: Enhancement of a Solid State Reaction by Proper Orientation within a Crystal. Part II. Micellar Effects on the Stereochemistry and Rate of Aqueous Solvolysis Reactions. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/QB90-WP98. https://resolver.caltech.edu/CaltechTHESIS:02222017-142615284
Abstract
Part I. The solid state rearrangement of methyl-p-dimethylaminobenzenesulfonate to the trimethylammoniumbenzenesulfonate zwitterion was studied by a combination of spectroscopic techniques. NMR, Field Desorption Mass Spectrometry, and X-Ray Crystallography were employed to determine the mechanism of this reaction. It was shown to be an intermolecular nucleophilic displacement whose rate is greatly enhanced by the crystallinity of the starting material.
Part II. A study of the effects of micelles on the aqueous solvolysis of alkyl-p-trimethylammoniumbenzenesulfonates revealed that anionic micelles could change the rate and stereochemistry of the solvolysis reaction. The mechanism for the observed rate retardation and induced decrease in stereochemical integrity was probed and a unified mechanistic hypothesis is presented.
Item Type: | Thesis (Dissertation (Ph.D.)) | ||||||
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Subject Keywords: | (Chemistry) | ||||||
Degree Grantor: | California Institute of Technology | ||||||
Division: | Chemistry and Chemical Engineering | ||||||
Major Option: | Chemistry | ||||||
Thesis Availability: | Public (worldwide access) | ||||||
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Defense Date: | 20 February 1976 | ||||||
Funders: |
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Record Number: | CaltechTHESIS:02222017-142615284 | ||||||
Persistent URL: | https://resolver.caltech.edu/CaltechTHESIS:02222017-142615284 | ||||||
DOI: | 10.7907/QB90-WP98 | ||||||
Default Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||
ID Code: | 10060 | ||||||
Collection: | CaltechTHESIS | ||||||
Deposited By: | Benjamin Perez | ||||||
Deposited On: | 22 Feb 2017 23:20 | ||||||
Last Modified: | 23 Aug 2024 23:36 |
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