Journal
JOURNAL OF MOLECULAR STRUCTURE
Volume 1295, Issue -, Pages -Publisher
ELSEVIER
DOI: 10.1016/j.molstruc.2023.136748
Keywords
Thiazolidinones; Proton tautomerism; Spectroscopic analysis; X-ray analysis; Quantum chemical computations
Categories
Ask authors/readers for more resources
In this article, we reported the recent findings of our systematic studies on the effects of phenyl-ring substituents on proton tautomerism and stereoisomerism in 4-phenylamino-1,3-thiazol-2(5H)-one derivatives. Through synthesis, spectral analysis, and crystal studies, we found that these compounds exist solely in the amino tautomeric form and exhibit a specific arrangement.
In this article, we have reported the most recent results of our systematic studies of phenyl-ring substituent effect on proton tautomerism and stereoisomerism in 4-phenylamino-1,3-thiazol-2(5H)-one derivatives. The work concerns the synthesis, analysis of 1H and 13C NMR and FT-IR spectra, and X-ray crystal studies of three isomeric compounds, i.e. 5-dimethylaminomethylidene-4-(o-,m-,p-methoxyphenyl)amino-1,3-thiazol-2(5H)-ones. All three isomers were found to solely exist in the amino tautomeric form, both in the DMSO solution and the solid phase. In the molecules of all the title compounds, the o-,m-,p-methoxyphenylamine residue has synperiplanar disposition with respect to the thiazolone system, while the 5-dimethylaminomethylidene residue adopts the Zconfiguration. DFT calculations correctly predict that the synperiplanar arrangement is favored in all investigated materials
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available