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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

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. http://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.))
Subject Keywords:Chemistry
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Bergman, Robert G.
Thesis Committee:
  • Unknown, Unknown
Defense Date:20 February 1976
Funders:
Funding AgencyGrant Number
NSFUNSPECIFIED
Achievement Rewards for College Scientists FoundationUNSPECIFIED
Record Number:CaltechTHESIS:02222017-142615284
Persistent URL:http://resolver.caltech.edu/CaltechTHESIS:02222017-142615284
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:22 Feb 2017 23:20

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