Gas-phase acidity of CH3X [X =P(CH3)2, SCH3, F, Cl, Br, or I] compounds
- 1 January 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 6,p. 837-840
- https://doi.org/10.1039/p29850000837
Abstract
Proton abstraction from (CH3)3P, CH3SCH3, CH3Cl, CH3Br, and CH3I in the gas phase has been investigated with the use of Fourier transform ion cyclotron resonance (FT-ICR) mass spectrometry. The gas-phase acidities of the three former compounds are reported to be ΔG°acid[(CH3)3P] 1 606 ± 8 kJ mol–1; ΔG°acid(CH3SCH3) 1 616 ± 8 kJ mol–1; and ΔG°acid(CH3Cl) 1 628 ± 12 kJ mol–1. The competition between proton abstraction and SN2 substitution in the reactions of different anions with CH3F, CH3Cl, CH3Br, and CH3I has been determined, Based upon these kinetic experiments, it is concluded that the gas-phase acidity increases down the series CH3F, CH3Cl, CH3Br, CH3I. The reactions of (CH3)PCH2 –, ClCH2 –, and BrCH2 – ions with various molecules are described.Keywords
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