Abstract
The nature of formaldazine was studied on the basis of the data from various spectroscopies and compared with that of butadiene, its hydrocarbon analog. The UV and far-infrared spectra showed that the delocalization of π-electrons of formaldazine is less than that of butadiene. The ionization potential of formaldazine was estimated by mass spectroscopy. It is smaller than those of butadiene and triethylamine and is larger than that of dimethylhydrazine. The first ionization comes from the lone pair of the nitrogen, because the unpaired electron has a coupling only with the nitrogen nucleus in the ESR spectrum of the ion salt, which was obtained by the reaction of formaldazine with chloranil. The half wave potential was determined by means of an extrapolation of the Taft’s plot of the half wave potentials of various α,ω-dialkylaldehyde azines (R—CH=N—N=CH—R) and used as a measure of their electron affinities. Formaldazine was found to have a larger electron affinity than acrylonitrile and butadiene. In conclusion, formaldazine is a compound which has both electron-donating and electron-accepting properties.
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Kamachi, M., Murahashi, S. The Polymerization of Formaldazine. I. The Nature of Formaldazine. Polym J 6, 295–301 (1974). https://doi.org/10.1295/polymj.6.295
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DOI: https://doi.org/10.1295/polymj.6.295