RESONANCE INTERACTIONS OF METHYLSULFONYL, METHYLTHIO AND RELATED GROUPINGS AS REVEALED BY HAMMETT SIGMA CONSTANTS
NORTHWESTERN UNIV EVANSTON IL CHEMICAL LAB
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The relative acidities of 8 m- and p-substituted thiophenols were obtained to determine the conjugative ability of the MeSO2 was significantly larger than that from BzOH, but smaller than that from phenols or anilines. This indicated the possibility of varying degrees of resonance interactions involving an expansion of the s valence shell to 10 electrons. The data also indicated that other groups which are capable of strong resonance interactions e.g., p-NO2, p-OMe may exhibit more than 1 sigma value, depending on the reactions involved. Prepared for publication in th J. Am. Chem. Soc..