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

doi:10.3390/i5110294

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

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

Patricia E. Allegretti ¹, María de las Mercedes Schiavoni ¹, María S. Cortizo ², Eduardo A. Castro ³^,* and Jorge J.P. Furlong ¹

¹ Laboratorio de Estudio de Compuestos Orgánicos (LADECOR), División Química Orgánica, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, (1900) La Plata, Buenos Aires, Argentina ² Instituto de Investigaciones Físico-Químicas, Teóricas y Aplicadas (INIFTA), Facultad de Ciencias Exactas, Universidad Nacional de La Plata, (1900) La Plata, Buenos Aires, Argentina ³ INIFTA (UNLP-CONICET), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Suc.4, C.C. 16, (1900) La Plata, Buenos Aires, Argentina

* Author to whom correspondence should be addressed.

Received: 31 January 2004; in revised form: 9 October 2004 / Accepted: 5 November 2004 / Published: 30 November 2004

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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 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. 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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