Chemistry Surrounding Monomeric Copper(l) Methyl, Phenyl, Anilido, Ethoxide, and Phenoxide Complexes Supported by N-Heterocyclic Carbene Ligands: Reactivity Consistent with Both Early and Late Transition Metal Systems

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Article on chemistry surrounding monomeric copper(I) methyl, phenyl, anilido, ethoxide, and phenoxide complexes supported by N-heterocyclic carbene ligands.

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14 p.

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Goj, Laurel A.; Blue, Elizabeth D.; Delp, Samuel A.; Gunnoe, T. Brent; Cundari, Thomas R., 1964-; Pierpont, Aaron W. et al. September 27, 2006.

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Article on chemistry surrounding monomeric copper(I) methyl, phenyl, anilido, ethoxide, and phenoxide complexes supported by N-heterocyclic carbene ligands.

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14 p.

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Reprinted with permission from Inorganic Chemistry. Copyright 2006 American Chemical Society.

Abstract: Monomeric copper(l) alkyl complexes that possess the N-heterocyclic carbene (NHC) ligands IPr, SIPr, and IMes [IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, SIPr = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene, IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene] react with amines or alcohols to release alkane and form the corresponding monomeric copper(l) amido, alkoxide, or aryloxide complexes. Thermal decomposition reactions of (NHC)Cu׀ methyl complexes at temperatures between 100 and 130 °C produce methane, ethane, and ethylene. The reactions of (NHC)Cu(NHPh) complexes with bromoethane reveal increasing nucleophilic reactivity at the anilido ligand in the order (SIPR)Cu(NHPh) < (IPr)Cu(NHPh) < (IMes)Cu(NHPh) < (dtbpe)Cu(NHPh) [dtbpe = 1,2-bis(di-tert-butylphosphino)ethane]. DFT calculations suggest that the HOMO for the series of Cu anilido complexes is localized primarily on the amido nitrogen with some pπanilido-dπCu π*-character. [(IPr)Cu(μ-H)]2 and (IPr)Cu(Ph) react with aniline to quantitatively produce (IPr)Cu(NHPh)/dihydrogen and (IPr)Cu(NHPh)/benzene, respectively. Analysis of the DFT calculations reveals that the conversion of [(IPr)Cu(μ-H)]2 and aniline to (IPr)Cu(NHPh) and dihydrogen is favorable with ∆H ≈ -7 kcal/mol and ∆G ≈ -9 kcal/mol.

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  • Inorganic Chemistry, 2006, Washington DC: American Chemical Society, pp. 9032-9045

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  • Publication Title: Inorganic Chemistry
  • Volume: 45
  • Issue: 22
  • Page Start: 9032
  • Page End: 9045
  • Pages: 14
  • Peer Reviewed: Yes

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  • September 27, 2006

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  • March 2, 2012, 11:47 a.m.

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  • May 12, 2014, 2:57 p.m.

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Goj, Laurel A.; Blue, Elizabeth D.; Delp, Samuel A.; Gunnoe, T. Brent; Cundari, Thomas R., 1964-; Pierpont, Aaron W. et al. Chemistry Surrounding Monomeric Copper(l) Methyl, Phenyl, Anilido, Ethoxide, and Phenoxide Complexes Supported by N-Heterocyclic Carbene Ligands: Reactivity Consistent with Both Early and Late Transition Metal Systems, article, September 27, 2006; [Washington, DC]. (digital.library.unt.edu/ark:/67531/metadc77128/: accessed April 25, 2017), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT College of Arts and Sciences.