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Volumn 126, Issue 11, 2004, Pages 3627-3641

Kinetics, Thermodynamics, and Effect of BPh3 on Competitive C-C and C-H Bond Activation Reactions in the Interconversion of Allyl Cyanide by [Ni(dippe)]

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COMPLEXATION; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; THERMAL EFFECTS; THERMODYNAMICS;

EID: 1642291793     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037002e     Document Type: Article
Times cited : (175)

References (73)
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    • note
    • 2-CN-3-pentenenitrile).
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    • 1H NMR spectrum
    • 1H NMR spectrum.
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    • Neutral Thermochemical Data
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    • Afeefy, H. Y.; Liebman, J. F.; Stein, S. E. Neutral Thermochemical Data. In NIST Chemistry WebBook, NIST Standard Reference Database Number 69; Linstrom, P. J., Mallard, W. G., Eds.; National Institute of Standards and Technology: Gaithersburg, MD 20899 (http://webbook.nist.gov), March 2003.
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    • note
    • 2Ni(π-1-methallyl)CN behaves much like 3, except that it grows in more slowly (reaching a maximum after 5 h of reaction time) and disappears more rapidly than 3.3
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    • note
    • 1H} NMR spectrum of unlabeled, 97% cis-2.
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    • note
    • 8 solvent resonance at 25.4 ppm.
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    • was written by B. A. Barshop, Department of Biological Chemistry, Washington University Medical School, St. Louis, MO 63110
    • KINSIM Version 3.3, 1983, was written by B. A. Barshop, Department of Biological Chemistry, Washington University Medical School, St. Louis, MO 63110. See: Barshop, B. A.; Wrenn, R. F.; Frieden, C. Anal. Biochem. 1983, 130, 134-145. FITSIM Version 1.63, 1987, was developed by C. T. Zimmerle. See: Zimmerle, C. T.; Patane, K.; Frieden, C. Biochemistry 1987, 26, 6545-6552.
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    • KINSIM Version 3.3, 1983, was written by B. A. Barshop, Department of Biological Chemistry, Washington University Medical School, St. Louis, MO 63110. See: Barshop, B. A.; Wrenn, R. F.; Frieden, C. Anal. Biochem. 1983, 130, 134-145. FITSIM Version 1.63, 1987, was developed by C. T. Zimmerle. See: Zimmerle, C. T.; Patane, K.; Frieden, C. Biochemistry 1987, 26, 6545-6552.
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    • was developed by C. T. Zimmerle
    • KINSIM Version 3.3, 1983, was written by B. A. Barshop, Department of Biological Chemistry, Washington University Medical School, St. Louis, MO 63110. See: Barshop, B. A.; Wrenn, R. F.; Frieden, C. Anal. Biochem. 1983, 130, 134-145. FITSIM Version 1.63, 1987, was developed by C. T. Zimmerle. See: Zimmerle, C. T.; Patane, K.; Frieden, C. Biochemistry 1987, 26, 6545-6552.
    • (1987) FITSIM Version 1.63
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    • 0023646693 scopus 로고
    • KINSIM Version 3.3, 1983, was written by B. A. Barshop, Department of Biological Chemistry, Washington University Medical School, St. Louis, MO 63110. See: Barshop, B. A.; Wrenn, R. F.; Frieden, C. Anal. Biochem. 1983, 130, 134-145. FITSIM Version 1.63, 1987, was developed by C. T. Zimmerle. See: Zimmerle, C. T.; Patane, K.; Frieden, C. Biochemistry 1987, 26, 6545-6552.
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    • For reviews of kinetic regression analysis methods, see: (a) Mannervick, B. Methods Enzymol. 1982, 63, 103-139.
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    • note
    • 31P NMR spectroscopy and reactions below 20 °C were too slow (>48 h reaction time) to leave in the NMR probe continuously. Also, at low temperatures, only small amounts of 3 were formed (<5% at 0 °C), making accurate integration difficult. Note that slightly poorer fits to the data are obtained at lower temperatures; see Supporting Information.
  • 46
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    • note
    • The trend toward less C-C activation at low temperatures is also supported by qualitative data collected at 0 °C (the maximum amount of 3 observed during the reaction was <5%) and -30 °C (no C-C bond cleavage was observed).
  • 47
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    • note
    • 1.
  • 48
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    • Institute of Physics, Rzeszow University of Technology, Al. Powstancow Warszawy 6, 35-959 Rzeszow, Poland
    • The nonlinear least squares program LSM was used to calculate the activation parameters from the rate constants and their errors. The program is available free of charge from the author, J. A. Mamczur, Institute of Physics, Rzeszow University of Technology, Al. Powstancow Warszawy 6, 35-959 Rzeszow, Poland, http://www.prz.rzeszow.pl/~janand/.
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    • (c) Haines, R. J.; Du Preez, A. L. J. Organomet. Chem. 1975, 84, 357-367. See also refs 6b, 27a, 28, and 29.
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    • note
    • iPr unit are always magnetically inequivalent, so at least two types of methyl groups will be observed in even the most symmetric (dippe)Ni complex. Also, the low-temperature NMR data do not allow differentiation between fast or slow rotation of the π-allyl group, although low-temperature data for 6 (vide infra) suggest that π-allyl rotation does not occur.
  • 62
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    • Carlton, L.; Weber, R. Inorg. Chem. 1996, 35, 5843-5850. See also ref 30.
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    • note
    • 8 resonance at 25.4 ppm; see ref 21.
  • 70
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    • note
    • 2 formed in the reaction. Also, note that less decomposition was observed at low temperatures as compared to that observed at high temperatures.
  • 71
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    • note
    • It has been noted that the integration program SAINT produces cell constant errors that are unreasonably small, because systematic error is not included. More reasonable errors might be estimated at 10x the listed value.
  • 73
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    • note
    • 2].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.