Two photoisomerization mechanisms of 4-Amino-3-penten-2-one (cas 1118-66-7): Hydrogen-atom migration and internal rotation

Add time:09/25/2019    Source:sciencedirect.com

Photoisomerization mechanism of 4-amino-3-penten-2-one, a chelated keto-enamine isomer, has been studied by low-temperature matrix-isolation infrared (IR) spectroscopy. Conformations of the reactant and two photoproducts were determined by comparison of the observed IR spectra with the calculated spectral patterns obtained by density-functional-theory (DFT) calculations. It is concluded that two isomers are produced upon UV irradiation: a non-chelated keto-enamine isomer by internal rotation around the CHC bond with breaking the intramolecular hydrogen bond, and an imino-enol isomer by hydrogen-atom migration from the amino group to the carbonyl group.

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