59951-57-4Relevant articles and documents
1H and 13C NMR spectra and isomerism of 3-aminoacroleins
Gomez-Sanchez, Antonio,Paredes-Leon, Rocio,Campora, Juan
, p. 154 - 162 (2007/10/03)
A set of 3-alkylaminoacroleins (R1NHCH=CHCH=O, R1 = alkyl) were studied by 13C and 1H NMR spectroscopy in solutions of different solvents and, for the simplest representative of the series, 3-methylaminoacrolein, at different temperatures. The equilibrium solutions of these compounds consists of mixtures of the chelated ZZE form (Z geometry around the =C - C=O single bond and the C=C bond, and E geometry around the C - N bond) and the two E configurational isomers having the E disposition around the =C - C=O single bond and differing in the disposition around the C - N bond (EEZ and EEE forms). The relative proportions of the three isomers depend on solvent polarity, concentration, bulk of substituent R1 and temperature. The EEZ isomer is the most abundant in polar solvents, while the concentration of the ZZE form increases in non-polar solvents and when increasing the bulk of R1. A lineshape 1H NMR study for 3-methylaminoacrolein in CDCl3 gave a ΔG? value of 66.0 kJ mol-1 at 303 K for the EEZ → EEE conversion. The presence of other tautomeric forms was not observed.
