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

• Main Authors: Marković R., Shirazi A., Džambaski Zdravko D., Baranac Marija M., Minić-Popović Dragica M.
• Format: Article
• Language: English
• Published: Serbian Chemical Society 2003-01-01
• Series: Journal of the Serbian Chemical Society
• Subjects: push-pull alkenes; hydrogen bonding; 1h-nmr spectroscopy.
• Online Access: http://www.doiserbia.nb.rs/img/doi/0352-5139/2003/0352-51390301001M.pdf
• ISSN: 0352-5139; 1820-7421

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.