Hindered Internal Rotation of N, N-Dimethylpropylamines

概要

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The N-methyls in 2,3-disubstituted N, N-dimethylpropylamines (I-VIII) have given two peaks with an equal intensity in an acid solution owing to the hindered internal rotation about the C-NMe_2H^+ bond. The energy barriers between two staggered forms have been estimated to be 0.7 (benzylthio)-7(thiocyanato) kcal mole^<-1> from the temperature dependence of the peak separations. The high-field shift and the largest separation of the N-methyls in the benzylthio derivative (I) have been ascribed to an anisotropic effect of the benzene ring. 1,3-Disubstituted 2-N, N-dimethylaminopropanes (IX) and 2-substituted N, N-dimethylethylamines (XII-XV) have shown a single peak for the N-methyls. A restricted rotation about the CH_2-CH bond in 2,N, N-trimethyl-aminoethyl disulfide (X) has been studied by the temperature dependence of the vicinal coupling constants.
社団法人日本薬学会の論文
1973-01-25