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

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  • Organic Chemistry

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Tierney, John ; Colasante, Neon ; Eagles, Jill ; Kelly, Stacey ; Lehmicke, Gabrielle ; Lucas, Omar ; Mannikarottu, Chino ; Mehmood, Osama ; Nguyen, Minh Luan D. ; Rai, Vaibhav ; Tsai, Jack ; Koyfman, Vladislav ; Mascavage, Linda M. ; Lagalante, Anthony F. / 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. In: Heterocyclic Communications. 2007 ; Vol. 13, No. 6. pp. 335-342.
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title = "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",
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.",
author = "John Tierney and Neon Colasante and Jill Eagles and Stacey Kelly and Gabrielle Lehmicke and Omar Lucas and Chino Mannikarottu and Osama Mehmood and Nguyen, {Minh Luan D.} and Vaibhav Rai and Jack Tsai and Vladislav Koyfman and Mascavage, {Linda M.} and Lagalante, {Anthony F.}",
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Tierney, J, Colasante, N, Eagles, J, Kelly, S, Lehmicke, G, Lucas, O, Mannikarottu, C, Mehmood, O, Nguyen, MLD, Rai, V, Tsai, J, Koyfman, V, Mascavage, LM & Lagalante, AF 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, vol. 13, no. 6, pp. 335-342. https://doi.org/10.1515/HC.2007.13.6.335

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

In: Heterocyclic Communications, Vol. 13, No. 6, 01.01.2007, p. 335-342.

Research output: Contribution to journalArticle

TY - JOUR

T1 - 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

AU - Tierney, John

AU - Colasante, Neon

AU - Eagles, Jill

AU - Kelly, Stacey

AU - Lehmicke, Gabrielle

AU - Lucas, Omar

AU - Mannikarottu, Chino

AU - Mehmood, Osama

AU - Nguyen, Minh Luan D.

AU - Rai, Vaibhav

AU - Tsai, Jack

AU - Koyfman, Vladislav

AU - Mascavage, Linda M.

AU - Lagalante, Anthony F.

PY - 2007/1/1

Y1 - 2007/1/1

N2 - 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.

AB - 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.

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