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I. The mechanism of aminations of halobenzenes. II. Quantum mechanical calculations of electrical effects of substituents in para-substituted anilines

Semenow, Dorothy Ann (1955) I. The mechanism of aminations of halobenzenes. II. Quantum mechanical calculations of electrical effects of substituents in para-substituted anilines. Dissertation (Ph.D.), California Institute of Technology. http://resolver.caltech.edu/CaltechETD:etd-01212004-110215

Abstract

PART I. The Mechanism of Aminations of Halobenzenes.

An elimination-addition mechanism, probably involving a "benzyne" intermediate, was established for the rearrangements which often occur in the conversion of non-activated aryl halides to arylamines with metallic amides. The evidence for the "benzyne" intermediate was obtained through 14C-tracer studies of rearrangements with iodobenzene, experiments designed to determine the role of the hydrogen atom located ortho to the displaced halogen atom and studies of orientations in the reactions of substituted halobenzenes.

PART II. Quantum Mechanical Calculations of Electrical Effects of Substituents in Para-substituted Anilines.

Calculations made by the simple molecular orbital method indicated that the relative basicities of aromatic amino groups para to electron-attracting substituents provide a reasonable measure of the charge on C4.

Item Type:Thesis (Dissertation (Ph.D.))
Degree Grantor:California Institute of Technology
Major Option:Chemistry
Thesis Committee:
  • Roberts, John D. (chair)
Defense Date:1 January 1955
Record Number:etd-01212004-110215
Persistent URL:http://resolver.caltech.edu/CaltechETD:etd-01212004-110215
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:260
Collection:CaltechTHESES
Deposited By: Imported from ETD-db
Deposited On:22 Jan 2004
Last Modified:25 Dec 2012 14:58

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