Reactions of charged substrates. 4. The gas-phase dissociation of (4-substituted benzyl) dimethylsulfoniums and-pyridiniums

N Buckley, D Maltby, AL Burlingame…

Index: Buckley, Neil; Maltby, David; Burlingame, Alma L.; Oppenheimer, Norman J. Journal of Organic Chemistry, 1996 , vol. 61, # 8 p. 2753 - 2762

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Citation Number: 14

Abstract

The relative rates for the gas-phase dissociation RX+→ R++ X° of five (4-Y-substituted benzyl) dimethysulfoniums (Y= MeO, Me, H, Cl, and NO2) and 24 (4-Y-substituted benzyl)-3'- Z-pyridiniums (complete series for Z= CN, Cl, CONH2, and H, and 4-methoxy-and 4- nitrobenzyls for Z= F and CH3CO) were measured using liquid secondary ion mass spectrometry. The Hammett plot (vs δΔ G° or σ+) is linear for the sulfoniums, but plots for ...