Absolute rate constants for the reactions of primary alkyl radicals with aromatic amines

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3778-3782

  Burton, Alan ^a   Ingold, K U ^a,b   Walton, J C ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000812996     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952162x     Document Type: Article

References (29)

1. 4 These complexities can be ignored for our present purposes because our work has been carried out under oxygen-free conditions.
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8. 9 and, in most experiments, the presence of an effective trap for the carbon-centered radicals which might otherwise have yielded esters and started a chain reaction.
9. -1 at 100°C. See: Hiatt, R. In Organic Peroxides; Swern, D., Ed.; Wiley-Interscience: New York, 1971; Vol. 2, Chapter 8.
10. The experimental points show some unexpected curvature which might be due to analytical errors or to a less than complete reaction scheme.
11. 2O in each reaction vial. See: Howard, J. A.; Ingold, K. U. Can J. Chem. 1962, 40, 1851-1864.
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16. Densities for dodecane were obtained from Table 20d in: Selected Values of Physical and Thermodynamic Properties of Hydrocarbons and Related Compounds; Rossini, F. D., Ed.; Carnegie Press: Pittsburgh, PA, 1953. These densities are 0.6900, 0.7048, and 0.7198 g/mL at 100, 80, and 60°C, respectively, corresponding to dodecane molarities of 4.05, 4.14, and 4.23 M at these three temperatures. We thank a reviewer for steering us to this data source.
17. There are no kinetic data for any similar reaction in solution listed by: Lorand, J. P. In Landolt Börnstein, New Series; Radical Reaction Rates in Solution; Fischer, H., Ed.; Springer-Verlag: Berlin, 1984; Vol. 13a, Chapter 2.
18. Benson, S. W. Thermochemical Kinetics, 2nd ed.; Wiley-Interscience : New York, 1976.
19. -1), E (kcal/mol): α-naphthylamine, 3.9, 1.0; phenyl-α-naphthylamine, 5.1, 1.0; β-naphthylamine, 5.0, 2.3; aniline, 6.6, 5.0.
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22. •.
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24. Certainly this appears to be true for methyl radicals. See: Wong, M. W.; Pross, A.; Radom, L. J. Am. Chem. Soc. 1993, 115, 11050-11051.
25. -1.
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