A preliminary study on predicting the 13C chemical shifts for a series of disubstituted 2,3-diphenyl-1,3-thiazolidin-4-ones

Article abstract of DOI:10.1515/HC.2005.11.3-4.215

A successful attempt has been made to predict ¹³C 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. The ¹³C chemical shifts for the C-2, C-4 and C-5 carbons of these compounds have previously been shown to correlate with Hammett σ constants and Swain Lupton dual substituent parameters. Because of these correlations we decided to investigate the potential for predicting ¹³C chemical shifts for C-2, C4 and C-5 in the thiazolidinone ring based on the known shifts for the two mono-substituted series of compounds. The effect of the substituents on the ¹³C 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 the ¹³C 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.

Full text of DOI:10.1515/HC.2005.11.3-4.215

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Download Date | 5/30/15 7:29 AM