28963-72-6Relevant articles and documents
Trends in alkyl substituent effects on nucleophilic reactions of carbonyl compounds: Gas phase reactions between ammonia and R1R2COCH3+ oxonium ions
Bache-Andreassen, Lihn,Uggerud, Einar
, p. 705 - 713 (2007/10/03)
The reactivity of carbonyl substituted methyl oxonium ions (R1R2COCH3-) towards ammonia has been investigated using an FT-ICR mass spectrometer and ab initio calculations. The monosubstituted ions (R1=H: R2 = H, CH3, C2H5 and i-C3H7) show different reaction patterns with variable degree of: (1) nucleophilic substitution, (2) addition elimination and (3) proton transfer, when reacted with ammonia. In all cases addition-elimination dominates over nucleophilic substitution, and the observed reactions are slow. The trends in reactivity are consistent with the alkyl group's electronic properties, as expressed by a single parameter linear or slightly non-linear model.