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Virginia Tech

Oxidative addition of amino acids to iridium(I) metal centers

Abstract

dc:description.abstract

The oxidative addition of both monosubstituted and disubstituted a.-amino acids to [Ir(COD)(PMe3)3]Cl (COD = cyclooctadiene) was studied and the reactivity of the resulting complexes was examined. The reaction of [Ir(COD)(PMe3)3]CI with the disubstituted amino acids, diphenylglycine and methyl phenyl alanine, led to an almost exclusive facial product. Monosubstituted amino acid complexes were observed to be mixtures of the meridional and facial isomers with the meridional isomer largely predominating. The meridional isomer was found to convert to the facial isomer when heated for several days at 100°C. In fact, a predominantly meridional mixture was found to convert to a predominantly facial mixture upon heating. The facial isomer was therefore shown to be the thermodynamic product from the mixture. Small amounts of other isomers were observed in the hydride region of the proton NMR spectrum. One resonance at -23.75 ppm disappeared upon heating t-butyl acetylene with the amino acid complex. The disappearance of this hydride resonance may indicate the insertion of the unsaturate into the Ir-H bond, or alternatively, the conversion of this isomer to a more thermodynamically stable isomer. Reactions of these complexes with methylpropiolate and acrylamide were attempted but evidence of an insertion product was not found.

Degree

thesis:*
Name thesis:degree_name
Master of Science
Level thesis:degree_level
masters
Discipline thesis:degree_discipline
Chemistry
Department dc:contributor.department
Chemistry
Grantor dc:publisher
Virginia Tech
Year dc:date.issued
1996

Author and committee

dc:creator, dc:contributor.*
Author dc:creator
  • Huff, Lisa Ann
Chair dc:contributor.committeechair
  • Merola, Joseph S.
Committee members dc:contributor.committeemember
  • Hanson, Brian E.
  • Tissue, Brian M.

Subjects

dc:subject × 4

Rights

dc:rights
Statement dc:rights
  • In Copyright
Language dc:language.iso
en

Identifiers

dc:identifier.*
Dc Identifier Other
etd-11072008-063318
OAI identifier oai:identifier
oai:vtechworks.lib.vt.edu:10919/45459

Chain of custody

source
Harvested from
Virginia Tech
Base URL
vtechworks.lib.vt.edu/oai/request
Last updated
2026-07-22
Source record
OAI-PMH GetRecord
citation

Huff, Lisa Ann. Oxidative addition of amino acids to iridium(I) metal centers. masters thesis, Virginia Tech, 1996. http://hdl.handle.net/10919/45459