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NMR study of substituent effects in 4-substituted and 4,4′-disubstituted diphenyl sulphoxides and sulphones

✍ Scribed by R. Chandrasekaran; S. Perumal; D. A. Wilson

Publisher
John Wiley and Sons
Year
1989
Tongue
English
Weight
556 KB
Volume
27
Category
Article
ISSN
0749-1581

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✦ Synopsis

The proton and carbon NMR spectra of nine 4-Xdiphenyl sulphoxides, seven 4-X-4'-N02diphenyl sulphoxides, eight 4,4'-X,diphenyl sulphoxides, eight 4X-diphenyl sulphones, seven 4-X4'-N02diphenyl sulphones and eight 4,4'-X,diphenyl sulphones have been obtained. Correlation of the ' ' C chemical shifts with the appropriate substituent chemical shifts (SCS) for monosubstituted benzenes (Lynch plots) does not show the enhancement of substituent effect at C-1 (para to the substituent) that was a feature of the corresponding sulphides studied earlier. Dual substituent parameter (DSP) correlations of the I3C chemical shifts with al/aao are excellent for carbons meta (C-2,6) and para (C-1) to the substituent. The trends for the series sulphides, sulpboxides, sulphones, where a decreasing response to the change of substituent is the general observation, are discussed. Changes of molecular conformation may also influence the transmission of electronic effects to the ring not carrying the variable substituent X.

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