Premium
Predominance of inductive over resonance substituent effect on 33 S NMR chemical shifts of 4‐substituted phenyl‐4′‐methylphenacyl sulfones
Author(s) -
Gawinecki Ryszard,
Kolehmainen Erkki,
Zakrzewski Andrzej,
Laihia Katri,
Ośmiałowski Borys,
Kauppinen Reijo
Publication year - 1999
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(199906)37:6<437::aid-mrc470>3.0.co;2-3
Subject(s) - substituent , chemistry , chemical shift , inductive effect , phenacyl , resonance (particle physics) , carbon 13 nmr , sulfur , proton nmr , fluorine 19 nmr , electronic effect , nuclear magnetic resonance spectroscopy , computational chemistry , stereochemistry , organic chemistry , steric effects , physics , particle physics
Abstract 33 S NMR chemical shifts have been determined for the first time for a series of 10 substituted phenacyl sulfones. Electron‐withdrawing and electron‐releasing substituents in 4‐substituted phenyl‐4′‐methylphenacyl sulfones, p ‐MeC 6 H 4 COCH 2 SO 2 C 6 H 4 R‐ p , cause a ‘reverse’ substituent effect on the 33 S NMR resonance. Dual‐substituent parameter (DSP) analysis of δ( 33 S) values revealed that the inductive effect of the substituent predominates over its resonance effect. This finding shows that the 33 S NMR chemical shifts are of importance in estimating the electronic properties of sulfur‐containing compounds. The 13 C and 17 O NMR chemical shifts of the title compounds are also discussed. Copyright © 1999 John Wiley & Sons, Ltd.