THE ELECTRONIC SPECTRA OF THE ALPHA-PHENYL KETIMINE GROUP
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Date
1954
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Ohio State University
Abstract
Evidence is presented that the alpha-phenyl ketimine ion behaves spectroscopically like the alpha-phenyl carbonyl group which has been demonstrated to give rise to a long wavelength electronic transition of unexpectedly high extinction.1,2 The spectrum of the stable alpha-phenyl ketimine ion, isomethadon ketimine hydrochloride, gives rise to a strong long wavelength band ($\epsilon = 5200$ at 256 mu) compared with the end spectrum only of the free base at shorter wavelengths. The corresponding spectra of the ion and free base of a stable alkyl-ketimine, fencholyl isopropyl (isopropyl 1-methyl-3-isopropylcyclopentyl) ketimine and some aryl-conjugated ketimines (phenyl isobutyl ketimine, diphenyl ketimine and phenyl o-tolyl ketimine) are presented for comparison. These spectra clearly support the validity of the above-described alpha-phenyl ketimine interaction band. The long wavelength band in the alpha-phenyl ketimine ion reported here and the alpha-phenyl carbonyl formerly $reported^{1,2}$ is interpreted from these data as arising from a $\pi$ electron transition.
Description
$^{1}$ W. D. Kumler, L. A. Strait, E. L. Alpen, J. Am. Chem. Soc. 72:1463 (1950) $^{2}$ E. L. Alpen, W. D. Kurnler, and L. A. Strait, J. Am. Chem. Soc. 72:4558 (1950)
Author Institution: Spectrographic Laboratory, University of California
Author Institution: Spectrographic Laboratory, University of California