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- W2317961526 abstract "A range of mononuclear organomagnesates [RMgX2]− were generated in the gas phase by decarboxylation of the magnesium carboxylate precursors [RCO2MgX2]− (R = Me, Et, Pr, iPr, tBu, vinyl, allyl, HC≡C, Ph, PhCH2, PhCH2CH2; X = Cl, Br, I). The gas-phase formation and unimolecular reactivity of these organomagnesates were examined using a combination of experiments carried out in linear ion trap and triple-quadrupole mass spectrometers and DFT calculations. Halide loss was found to directly compete with decarboxylation in the formation of mononuclear [RMgX2]−. However, sterically unhindered, stable R– substituents and strong Mg–Cl bonds can be employed to facilitate the decarboxylation reaction at the expense of the halide loss channel. Thus, in the case of R = HC≡C, PhCH2, decarboxylation is the main fragmentation pathway. The resultant mononuclear organomagnesates [RMgX2]− were mass-selected, and their unimolecular chemistry was examined. Four competing fragmentations were observed: bond homolysis, bond heterolysis, halide loss, and β-hydride transfer. Which of these competing reactions dominates depends on the nature of R and X. A conjugatively stabilized R• allows the observation of [MgX2]•–, whereas the presence of a β-hydride generates [HMgX2]−. Weaker Mg–X bonds (e.g., Br and I) promote the formation of X– upon CID." @default.
- W2317961526 created "2016-06-24" @default.
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- W2317961526 creator A5075594544 @default.
- W2317961526 creator A5089340124 @default.
- W2317961526 date "2013-04-05" @default.
- W2317961526 modified "2023-10-10" @default.
- W2317961526 title "Gas-Phase Formation and Fragmentation Reactions of the Organomagnesates [RMgX2]−" @default.
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- W2317961526 doi "https://doi.org/10.1021/om3011917" @default.
- W2317961526 hasPublicationYear "2013" @default.
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