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Effects and Conformational Analysis of Some Substituted 2,3-Diphenyl-1,3-thiazolidin-4-ones

✍ Scribed by John Tierney; Gregory Houghton; Kimberley Sanford; Linda Mascavage; Mary McCoy; Alfred Findeisen; James Kilburn

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 412 KB
Volume: 34
Category: Article
ISSN: 0749-1581
DOI: 10.1002/(sici)1097-458x(199608)34:8<573::aid-omr928>3.0.co;2-d

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✦ Synopsis

Substituents placed on the phenyl rings of 2,3-diphenyl-1,3-thiazolidin-4-one affect the electron density surrounding both the methine proton and the C(2) carbon. These changes are reflected in the differing chemical shifts for these atoms relative to the parent compound. The other carbons in the heterocyclic ring appear to be similarly affected by substituents on the phenyl rings. Correlations for the effects of various substitnents in both the 2and 3-phenyl rings with the 'H and I3C chemical shifts for the aforementioned sites are discussed using both Hammett and Swain-Lupton dual parameter methods. A conformational analysis using ab initio calculations is in agreement with the observed NMR data.

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