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synthesis and reactivity of nucleophile assisting leaving groups

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Date Issued:
2006
Summary:
The synthesis and reactivity of Nucleophile Assisting Leaving Groups was studied in order to assess the rate enhancement of nucleophilic substitution reactions. Various Nucleophile Assisting leaving groups were synthesized, all of them containing a coordinating arm positioned ortho to an electrophilic center on a benzene ring. The various coordinating arms had novel geometries and binding properties. Their reactivity was studied with a variety of metal salts and the kinetics of the reactions was studied with 1H-NMR spectroscopy. This method provided a quantitative measurement of the rate enhancement observed in the substitution reactions from the rate constants obtained. In the case of certain crown ether-containing substrates, NMR experiments suggest that the mechanism of substitution proceeds in two steps, the first being a pre-coordination of the metal salt with the coordinating arm, followed by a conversion of the complex to products.
Title: The synthesis and reactivity of nucleophile assisting leaving groups.
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Name(s): Cohn, Pamela.
Florida Atlantic University, Degree grantor
Lepore, Salvatore D., Thesis advisor
Type of Resource: text
Genre: Electronic Thesis Or Dissertation
Issuance: monographic
Date Issued: 2006
Publisher: Florida Atlantic University
Place of Publication: Boca Raton, Fla.
Physical Form: application/pdf
Extent: 110 p.
Language(s): English
Summary: The synthesis and reactivity of Nucleophile Assisting Leaving Groups was studied in order to assess the rate enhancement of nucleophilic substitution reactions. Various Nucleophile Assisting leaving groups were synthesized, all of them containing a coordinating arm positioned ortho to an electrophilic center on a benzene ring. The various coordinating arms had novel geometries and binding properties. Their reactivity was studied with a variety of metal salts and the kinetics of the reactions was studied with 1H-NMR spectroscopy. This method provided a quantitative measurement of the rate enhancement observed in the substitution reactions from the rate constants obtained. In the case of certain crown ether-containing substrates, NMR experiments suggest that the mechanism of substitution proceeds in two steps, the first being a pre-coordination of the metal salt with the coordinating arm, followed by a conversion of the complex to products.
Identifier: 9780542745843 (isbn), 13375 (digitool), FADT13375 (IID), fau:10225 (fedora)
Collection: FAU Electronic Theses and Dissertations Collection
Note(s): Thesis (M.S.)--Florida Atlantic University, 2006.
Charles E. Schmidt College of Science
Subject(s): Chemical reaction, Conditions and laws of
Organic reaction mechanisms
Intermediates (Chemistry)
Organotransition metal compounds
Held by: Florida Atlantic University Libraries
Persistent Link to This Record: http://purl.flvc.org/fcla/dt/13375
Sublocation: Digital Library
Use and Reproduction: Copyright © is held by the author with permission granted to Florida Atlantic University to digitize, archive and distribute this item for non-profit research and educational purposes. Any reuse of this item in excess of fair use or other copyright exemptions requires permission of the copyright holder.
Use and Reproduction: http://rightsstatements.org/vocab/InC/1.0/
Host Institution: FAU
Is Part of Series: Florida Atlantic University Digital Library Collections.