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Nuclear Magnetic Resonance Spectroscopy. Kinetics of Isomerization of Para-Substituted Hexafluoroacetone N-Phenylimines

Roberts, John D. and Hall, George E. and Middleton, William J. (1971) Nuclear Magnetic Resonance Spectroscopy. Kinetics of Isomerization of Para-Substituted Hexafluoroacetone N-Phenylimines. Journal of the American Chemical Society, 93 (19). pp. 4778-4781. ISSN 0002-7863. doi:10.1021/ja00748a019.

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The kinetics of the degenerate isomerization about the carbon-nitrogen double bond of hexafluoroacetone N-phenylimine and its p-chloro, p-fluoro, p-methoxy, p-methyl, and p-nitro derivatives have been studied by line-shape analysis of nmr spectra at a series of temperatures. The free energies of activation at 25º were found to be 15.45, 15.53, 15.35, 14.35, 15.14, and 14.90 kcal mol^(-1), respectively. With the exception of the p-nitro compound, the rate constants at 25º give a Hammett plot with a linear correlation coefficient of 0.989 when σ^+ substituent constants are used; the p value is -0.980. The results are interpreted as being the consequence of an inplane inversion about the imine nitrogen of the p-nitro compound and a rotation about the imine carbon-nitrogen bond of the others.

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Additional Information:© 1971 American Chemical Society. Received October 26, 1970. The portion of this work carried out at the California Institute of Technology was supported by National Science Foundation.
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Caltech Gates and Crellin Laboratories4142
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Official Citation:Nuclear magnetic resonance spectroscopy. Kinetics of isomerization of p-substituted hexafluoroacetone N-phenylimines John D. Roberts, George E. Hall, and William J. Middleton Journal of the American Chemical Society 1971 93 (19), 4778-4781 DOI: 10.1021/ja00748a019
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60986
Deposited By: Ruth Sustaita
Deposited On:15 Oct 2015 04:29
Last Modified:10 Nov 2021 22:42

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