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 Scopus citations

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

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Fingerprint Dive into the research topics of 'A preliminary study on predicting the<sup>13</sup>c chemical shifts for a series of disubstituted 2,3-diphenyl-l,3-thiazolidin-4-ones'. Together they form a unique fingerprint.

  • Cite this