The nuclear magnetic resonance spectra of some related alkylene-substituted diethylamines

Abstract

The nuclear magnetic resonance spectra of N1, N1-diethyl-2,2-dimethylpropane-1,3-diamine (I), bis-(3-diethylamino-2,2-dimethylpropyl) amine (II) and N1-(3-diethylamino-2,2-dimethyl) propylidene-N3, N3-diethyl-2,2-dimethyl-1,3-propanediamine (III) are examined. In the spectrum of I, separate single peaks are observed for the methylene groups adjacent to the primary and tertiary nitrogen atoms. In the spectrum of II, the symmetrical secondary amine, the pair of methylene groups adjacent to the secondary nitrogen atom appears as a singlet separate from the methylene protons between the tertiary carbon and nitrogen atoms. Acetylation of I and II makes it possible to identify the methylene signals of each compound. In the spectrum of III, dissymmetry because of unsaturation [Formula: see text] is responsible for the differences in the peak positions of the signals of seemingly similar groups. This difference extends to the signals for the terminal methyl protons, which are six and seven bonds from the double bond.