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Volumn 130, Issue 39, 2008, Pages 13051-13058

Catalytic tuning of a phosphinoethane ligand for enhanced C-H activation

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE SPECIES; AMIDE BOND; BIPYRIDINE; BOND STRENGTH; C-H ACTIVATION; C-H BOND; CYCLOHEXADIENE; ENTHALPIC BARRIERS; HYDROGEN ATOM ABSTRACTION; NITRENE; NITRENES; PRECATALYST; THERMODYNAMICS AND KINETICS; TRIFLUOROMETHYL;

EID: 67650535867     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja803176j     Document Type: Article
Times cited : (30)

References (96)
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    • Gaussian Inc, Wallingford, CT
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    • (2004) Gaussian 03, Revision , Issue.C.02
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    • 67650548384 scopus 로고    scopus 로고
    • Using the reported gas-phase enthalpies of formation of 1,4-cyclohexadiene (24-26 kcal/mol, the cyclohexadienyl radical (45.7 kcal/mol, and the hydrogen atom (52.1 kcal/mol) indicates a C-H bond energy in 1,4-cyclohexadiene of 72-74 kcal/mol. The enthalpy of formation of the cyclohexadienyl radical is taken from the literature, Nicovich, J. M, Ravishankara, J. Phys. Chem. 1984, 88, 2534, while the other values come from the NIST Webbook
    • Using the reported gas-phase enthalpies of formation of 1,4-cyclohexadiene (24-26 kcal/mol), the cyclohexadienyl radical (45.7 kcal/mol), and the hydrogen atom (52.1 kcal/mol) indicates a C-H bond energy in 1,4-cyclohexadiene of 72-74 kcal/mol. The enthalpy of formation of the cyclohexadienyl radical is taken from the literature ( Nicovich, J. M.; Ravishankara, J. Phys. Chem. 1984, 88, 2534), while the other values come from the NIST Webbook (http://webbook.nist.gov).
  • 69
    • 9144224810 scopus 로고    scopus 로고
    • The analysis was limited to neutral complexes in which the Ni-N amine bond was acylic and the R factor was >10, a Allen, F. H, Taylor, R. Chem. Soc. Rev. 2004, 33, 463
    • The analysis was limited to neutral complexes in which the Ni-N amine bond was acylic and the R factor was >10%. (a) Allen, F. H.; Taylor, R. Chem. Soc. Rev. 2004, 33, 463.
  • 71
    • 0343730296 scopus 로고    scopus 로고
    • A crystal structure with the dfmpe ligand has been reported: Field, L. D.; Wilkinson, M. P. Organometallics 1997, 16, 1841.
    • A crystal structure with the dfmpe ligand has been reported: Field, L. D.; Wilkinson, M. P. Organometallics 1997, 16, 1841.
  • 72
    • 25644448112 scopus 로고    scopus 로고
    • See also the following papers detailing syntheses and chemistry of dfmpe and its metal complexes
    • See also the following papers detailing syntheses and chemistry of dfmpe and its metal complexes: Murphy-Jolly, M. B.; Lewis, L. C.; Caffyn, A. J. M. Chem. Commun. 2005, 4479.
    • (2005) Chem. Commun , pp. 4479
    • Murphy-Jolly, M.B.1    Lewis, L.C.2    Caffyn, A.J.M.3
  • 79
    • 0242669328 scopus 로고    scopus 로고
    • Using the methods described in the literature (Cooney, K. D, Cundari, T. R, Hoffman, N. W, Pittard, K. A, Temple, M. D, Zhao, Y. J. Am. Chem. Soc. 2003, 125, 4318) both P(CF3)3 and P(C2F5)3 were found to have similar electronic and structural impacts
    • 3 were found to have similar electronic and structural impacts.
  • 80
    • 67650559901 scopus 로고    scopus 로고
    • New routes to cationic nickel(III) imido complexes: Anderson, J. S.; Miller, A. J. M.; Iluc, V.; Hillhouse, G. L. Presented at the 37th Great Lakes Regional Meeting of the American Chemical Society, Milwaukee, WI, May 31-June 2, 2006; GLRM-340.
    • (a) "New routes to cationic nickel(III) imido complexes": Anderson, J. S.; Miller, A. J. M.; Iluc, V.; Hillhouse, G. L. Presented at the 37th Great Lakes Regional Meeting of the American Chemical Society, Milwaukee, WI, May 31-June 2, 2006; GLRM-340.
  • 81
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    • New group transfer reactions of nickel-carbene and nickel-imido complexes: Harrold, N. D.; Waterman, R.; Hillhouse, G. L. Presented at the 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007; INOR-682.
    • (b) "New group transfer reactions of nickel-carbene and nickel-imido complexes": Harrold, N. D.; Waterman, R.; Hillhouse, G. L. Presented at the 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007; INOR-682.
  • 92
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    • Koo and Hillhouse have identified C-N bond formation via reductive elimination from nickel(alkyl)amido complexes, albeit with bipyridine supporting ligation: Koo, K.; Hillhouse, G. L. Organometallics 1995, 14, 4421.
    • Koo and Hillhouse have identified C-N bond formation via reductive elimination from nickel(alkyl)amido complexes, albeit with bipyridine supporting ligation: Koo, K.; Hillhouse, G. L. Organometallics 1995, 14, 4421.


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