Relative Reactivity of Toluene-Benzene in Nitronium Tetrafluoroborate Nitration: Limitation of the Competitive Method of Rate Determination in Fast Reactions

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A study was made to determine the relative reactivity of the toluene–benzene pair in a nitronium salt nitration, using the method of competitive rate determination. Despite difficulties encountered in ensuring homogeneous reaction conditions owing to the high speed of reaction the relative rates (toluene/benzene) obtained under certain conditions attained a range (25–30) which is considered to represent the range of relative reactivity and it corresponds to the known reactivity of toluene-benzene in nitric acid nitration. On the basis of these results there seems to be no reason to suppose that nitronium salt nitration involves a mechanism different from that of the nitric acid nitration.