A preliminary study on predicting the13c chemical shifts for a series of disubstituted 2,3-diphenyl-l,3-thiazolidin-4-ones

John Tierney, Douglas Sheridan, Linda Mascavage, Daniela Gorbecheva, Michelle Ripp, Sonjoo Son

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A successful attempt has been made to predict13C chemical shifts for a series of disubstituted 2,3-diphenyl-1,3-thiazolidin-4-ones. Prior work has shown that substituents placed on either phenyl ring of the 2,3-diphenyl-1,3-thiazolidin-4-one system affect the electron density surrounding the C-2, C-4 and C-5 atoms. These changes are reflected in the different nmr chemical shifts for these carbon atoms relative to the unsubstituted compound. The13C chemical shifts for the C-2, C-4 and C-5 carbons of these compounds have previously been shown to correlate with Hammett a constants and Swain Lupton dual substituent parameters. Because of these correlations we decided to investigate the potential for predicting13C chemical shifts for C-2, C4 and C-5 in the thiazolidinone ring based on the known shifts for the two monosubstituted series of compounds. The effect of the substituents on the13C chemical shifts for the C-2, C-4 and C-5 carbons in the disubstituted 2,3-diphenylthiazolidinones are discussed relative to the two mono-substituted 2,3-diphenylthiazolidinone series. The data is then used to predict the13C chemical shift values at C-2, C-4 and C-5 in the thiazolidinone ring with all possible substituents combinations in the 2-phenyl and 3-phenyl rings.

Original languageEnglish (US)
Pages (from-to)215-222
Number of pages8
JournalHeterocyclic Communications
Volume11
Issue number3-4
DOIs
StatePublished - Jan 1 2005

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Chemical shift
Carbon
Atoms
Carrier concentration
diphenyl

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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Tierney, John ; Sheridan, Douglas ; Mascavage, Linda ; Gorbecheva, Daniela ; Ripp, Michelle ; Son, Sonjoo. / A preliminary study on predicting the13c chemical shifts for a series of disubstituted 2,3-diphenyl-l,3-thiazolidin-4-ones. In: Heterocyclic Communications. 2005 ; Vol. 11, No. 3-4. pp. 215-222.
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A preliminary study on predicting the13c chemical shifts for a series of disubstituted 2,3-diphenyl-l,3-thiazolidin-4-ones. / Tierney, John; Sheridan, Douglas; Mascavage, Linda; Gorbecheva, Daniela; Ripp, Michelle; Son, Sonjoo.

In: Heterocyclic Communications, Vol. 11, No. 3-4, 01.01.2005, p. 215-222.

Research output: Contribution to journalArticle

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