Enol and Enethiol Occurrence for Some Ketones and Thioketones. Mass Spectrometry and Theoretical Calculations

Patricia Allegretti, María de las Mercedes Schiavoni, María Cortizo, Eduardo Castro, Jorge Furlong
2004 International Journal of Molecular Sciences  
The mass spectra of ketones can provide valuable information with regards to keto-enol equilibria occurring in the gas phase. Mass spectra of selected ketones and thioketones have been analysed and specific fragmentation assignments have been done to characterised and weigh co-existing keto and enol tautomers. Thioketones are of particular interest due to their tendency to shift the tautomeric equilibrium towards the enethiol form. The predictive value of this methodology is not only supported
more » ... y the influence of these compound's nature and size of the substituent on these equilibria but also by the good correlation found between the selected fragments abundances ratio and semi-empirical calculation (AM1) of the corresponding heats of tautomerization.
doi:10.3390/i5110294 fatcat:ofj5lstulvcbbdlsylattie5j4