Substituent effects using 13C chemcial shifts for a series of substituted 2-phenyl-3-(pyridin-2-yl)-1,3-thiazolidin-4-ones with a comparison to similarly substituted 1,3-thiazolidin-4-ones

John Tierney, Neon Colasante, Jill Eagles, Stacey Kelly, Gabrielle Lehmicke, Omar Lucas, Chino Mannikarottu, Osama Mehmood, Minh Luan D. Nguyen, Vaibhav Rai, Jack Tsai, Vladislav Koyfman, Linda M. Mascavage, Anthony F. Lagalante

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Abstract

Substituted 2,3-diphenyl-1,3-thiazolidin-4-ones and substituted 3-benzyl-2-phenyl-1,3-thiazolidin-4-ones have been shown to exhibit good correlations using 13C chemical shift measurements (substituents chemical shifts or ses) for substituents placed on the phenyl and benzyl moieties versus Hammett a constants; the chemical shifts for C(2), C(4) and C(5) in the thiazolidinone ring have been the focus of interest. In some instances the correlations can be further improved by using dual substituent parameters. In this study the effects of substituents on 13C chemical shifts in the thiazolidinone ring at C(2), C(4) and C(5) were measured for a series of substituted 2-phenyl-3-pyridin2-yl-1,3-thiazolidin-4-ones. The chemical shift changes were compared to the two aforementioned series of thiazolidin-4-ones.

Original languageEnglish (US)
Pages (from-to)335-342
Number of pages8
JournalHeterocyclic Communications
Volume13
Issue number6
DOIs
StatePublished - Jan 1 2007

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Tierney, J., Colasante, N., Eagles, J., Kelly, S., Lehmicke, G., Lucas, O., Mannikarottu, C., Mehmood, O., Nguyen, M. L. D., Rai, V., Tsai, J., Koyfman, V., Mascavage, L. M., & Lagalante, A. F. (2007). Substituent effects using 13C chemcial shifts for a series of substituted 2-phenyl-3-(pyridin-2-yl)-1,3-thiazolidin-4-ones with a comparison to similarly substituted 1,3-thiazolidin-4-ones. Heterocyclic Communications, 13(6), 335-342. https://doi.org/10.1515/HC.2007.13.6.335