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An examination of the pK a 's of a series of phenacyl 'onium salts has indicated that the acidifying effects of the 'onium groups increase in the order arsonium < phosphonium < sulfonium. The acidifying effects of the 'onium atom substituents increase in the order methyl < n-butyl < phenyl. These observations have been accounted for in terms of pπ–dπ overlap between the carbanion and the heteroatom of the 'onium group.
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Johnson et al. (1968) studied this question.
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