A second study - predicting the 13C chemical shifts for a series of substituted 3-(4-methoxyphenyl)-2-phenyl-1,3-Thiazolidin-4-ones

John Tierney, Vladislav Koyfmann, Kevin Cannon, Linda Mascavage, Anthony Lagalante

Research output: Contribution to journalArticle

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Abstract

Previously, an 'additivity' equation relating experimental 13C chemical shift data for two mono-substituted diphenyl-1,3-thiazolidin-4-one series was developed to predict chemical shifts for a similarly substituted bis-disubstituted thiazolidinone series. The sites of interest in the 1,3-thiazolidin-4-one are the C-2, C-4, and C-5 carbons. The empirically derived equation for predicting the chemical shifts is □xy= □h + (□x-□h) + (□y- □h) where □xy is the predicted chemical shift for the disubstituted thiazolidinone, □h is the experimental chemical shift for the unsubstituted thiazolidinone, □xDx is the experimental chemical shift for substituent in the 2-phenyl ring, and □y is the experimental chemical shift for substituent in the N-(3)-phenyl ring. This article discusses the application of the aforementioned equation with respect to a new series of substituted-2-phenyl-3-methoxyphenyl-1, 3-thiazolidin-4-ones, where the substituents on both phenyl rings are not the same. The equation was shown to predict a less exact chemical shift in this one test series than for the previous bis-disubstituted series of compounds.

Original languageEnglish (US)
Pages (from-to)453-460
Number of pages8
JournalHeterocyclic Communications
Volume14
Issue number6
StatePublished - Dec 1 2008

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Chemical shift
Carbon

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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Tierney, John ; Koyfmann, Vladislav ; Cannon, Kevin ; Mascavage, Linda ; Lagalante, Anthony. / A second study - predicting the 13C chemical shifts for a series of substituted 3-(4-methoxyphenyl)-2-phenyl-1,3-Thiazolidin-4-ones. In: Heterocyclic Communications. 2008 ; Vol. 14, No. 6. pp. 453-460.
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abstract = "Previously, an 'additivity' equation relating experimental 13C chemical shift data for two mono-substituted diphenyl-1,3-thiazolidin-4-one series was developed to predict chemical shifts for a similarly substituted bis-disubstituted thiazolidinone series. The sites of interest in the 1,3-thiazolidin-4-one are the C-2, C-4, and C-5 carbons. The empirically derived equation for predicting the chemical shifts is □xy= □h + (□x-□h) + (□y- □h) where □xy is the predicted chemical shift for the disubstituted thiazolidinone, □h is the experimental chemical shift for the unsubstituted thiazolidinone, □xDx is the experimental chemical shift for substituent in the 2-phenyl ring, and □y is the experimental chemical shift for substituent in the N-(3)-phenyl ring. This article discusses the application of the aforementioned equation with respect to a new series of substituted-2-phenyl-3-methoxyphenyl-1, 3-thiazolidin-4-ones, where the substituents on both phenyl rings are not the same. The equation was shown to predict a less exact chemical shift in this one test series than for the previous bis-disubstituted series of compounds.",
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A second study - predicting the 13C chemical shifts for a series of substituted 3-(4-methoxyphenyl)-2-phenyl-1,3-Thiazolidin-4-ones. / Tierney, John; Koyfmann, Vladislav; Cannon, Kevin; Mascavage, Linda; Lagalante, Anthony.

In: Heterocyclic Communications, Vol. 14, No. 6, 01.12.2008, p. 453-460.

Research output: Contribution to journalArticle

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AU - Tierney, John

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AU - Mascavage, Linda

AU - Lagalante, Anthony

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AB - Previously, an 'additivity' equation relating experimental 13C chemical shift data for two mono-substituted diphenyl-1,3-thiazolidin-4-one series was developed to predict chemical shifts for a similarly substituted bis-disubstituted thiazolidinone series. The sites of interest in the 1,3-thiazolidin-4-one are the C-2, C-4, and C-5 carbons. The empirically derived equation for predicting the chemical shifts is □xy= □h + (□x-□h) + (□y- □h) where □xy is the predicted chemical shift for the disubstituted thiazolidinone, □h is the experimental chemical shift for the unsubstituted thiazolidinone, □xDx is the experimental chemical shift for substituent in the 2-phenyl ring, and □y is the experimental chemical shift for substituent in the N-(3)-phenyl ring. This article discusses the application of the aforementioned equation with respect to a new series of substituted-2-phenyl-3-methoxyphenyl-1, 3-thiazolidin-4-ones, where the substituents on both phenyl rings are not the same. The equation was shown to predict a less exact chemical shift in this one test series than for the previous bis-disubstituted series of compounds.

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