Hydrogen bonding in push-pull 5-substituted-2-alkylidene-4-oxothiazolidines: ¹H-NMR spectroscopic study

Abstract

Application of dynamic 1H-NMR spectroscopy added to the understanding of the hydrogen bonds existing in the structurally related 5-substituted-2-alkylidene-4-oxothiazolidines in polar and apolar solvents. The equilibrated mixtures of these typical push-pull alkenes in CDCl3 consist of the intramolecularly H-bonded (E)-isomer and intermolecularly H-bonded (Z)-isomer in varying proportions which depend on the solvent polarity. For the representative of the series. (Z)-2-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-1-phenylethanone, a concentration effect on the degree of intermolecular hydrogen bonding in apolar CDCl3 has been studied.