Int. J. Mol. Sci. 2004, 5(11), 294-300; doi:10.3390/i5110294
Article

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

1, 1, 2, 3,* email and 1
Received: 31 January 2004; in revised form: 9 October 2004 / Accepted: 5 November 2004 / Published: 30 November 2004
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: 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 by 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.
Keywords: Tautomerism; ketones; mass spectrometry; theoretical calculations
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MDPI and ACS Style

Allegretti, P.E.; Schiavoni, M.M.; Cortizo, M.S.; Castro, E.A.; Furlong, J.J.P. Enol and Enethiol Occurrence for Some Ketones and Thioketones. Mass Spectrometry and Theoretical Calculations. Int. J. Mol. Sci. 2004, 5, 294-300.

AMA Style

Allegretti PE, Schiavoni MM, Cortizo MS, Castro EA, Furlong JJP. Enol and Enethiol Occurrence for Some Ketones and Thioketones. Mass Spectrometry and Theoretical Calculations. International Journal of Molecular Sciences. 2004; 5(11):294-300.

Chicago/Turabian Style

Allegretti, Patricia E.; Schiavoni, María de las Mercedes; Cortizo, María S.; Castro, Eduardo A.; Furlong, Jorge J.P. 2004. "Enol and Enethiol Occurrence for Some Ketones and Thioketones. Mass Spectrometry and Theoretical Calculations." Int. J. Mol. Sci. 5, no. 11: 294-300.


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