An inverted relationship between stability and rate of formation of Meisenheimer-type adducts from dinitrothiophen and trinitrobenzene derivatives

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Abstract
A σ-adduct (II) is formed by the action of the methoxide ion on 2,4-dinitrothiophen; the equilibrium and rate constants for this process have been determined at 25° in methanol and the striking differences between the dinitrothiophen and the trinitrobenzene systems are discussed.