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Effects and Conformational Analysis of Some Substituted 2,3‐Diphenyl‐1,3‐thiazolidin‐4‐ones
Author(s) -
Tierney John,
Houghton Gregory,
Sanford Kimberley,
Mascavage Linda,
McCoy Mary,
Findeisen Alfred,
Kilburn James
Publication year - 1996
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199608)34:8<573::aid-omr928>3.0.co;2-d
Subject(s) - chemistry , chemical shift , ring (chemistry) , carbon 13 nmr , ab initio , computational chemistry , proton nmr , proton , stereochemistry , crystallography , organic chemistry , physics , quantum mechanics
Substituents placed on the phenyl rings of 2,3‐diphenyl‐1,3‐thiazolidin‐4‐one affect the electron density surrounding both the methine proton and the C(2) carbon. These changes are reflected in the differing chemical shifts for these atoms relative to the parent compound. The other carbons in the heterocyclic ring appear to be similarly affected by substituents on the phenyl rings. Correlations for the effects of various substituents in both the 2‐ and 3‐phenyl rings with the 1 H and 13 C chemical shifts for the aforementioned sites are discussed using both Hammett and Swain–Lupton dual parameter methods. A conformational analysis using ab initio calculations is in agreement with the observed NMR data.