Substituent effects for some substituted 3-benzyl-2-phenyl-1,3-thiazolidin-4-ones using 1H and 13C NMR

John Tierney, Douglas Sheridan, Kathy Kovalesky, Linda M. Mascavage, Kimberly Schneider, Carrie Sheely

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

Substituents placed on the phenyl rings of 3-benzyl-2-phenyl-1,3-thiazolidin-4-one affect the electron density surrounding both the methine proton, Hm, at C(2), Ha and Hb at C(5), and Hc and Hd at the benzyl carbon. The electron density changes are also exhibited at the C(2), C(4), C(5) and the benzyl carbons. These electron density changes are reflected, respectively, in the differing chemical shifts for the 1H and 13C NMR spectra for these atoms relative to the unsubstituted compound. Correlations for the effects of various substituents in both the 2-phenyl and 3-benzyl rings with the 1H and 13C chemical shifts, for the aforementioned sites, are discussed using Hammett σ constants. The large chemical shift difference observed for the geminal N-benzylic protons, Hc and Hd is discussed.

Original languageEnglish (US)
Pages (from-to)105-111
Number of pages7
JournalHeterocyclic Communications
Volume6
Issue number2
StatePublished - Dec 1 2000

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Tierney, J., Sheridan, D., Kovalesky, K., Mascavage, L. M., Schneider, K., & Sheely, C. (2000). Substituent effects for some substituted 3-benzyl-2-phenyl-1,3-thiazolidin-4-ones using 1H and 13C NMR. Heterocyclic Communications, 6(2), 105-111.