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

International Journal of Molecular Sciences

Patricia E. Allegretti²  Mar໚ de las Mercedes Schiavoni²  Mar໚ Susana Cortizo³  Eduardo A. Castro¹ 

[1] 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.;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.;Instituto de Investigaciones Físico-Químicas, Teóricas y Aplicadas (INIFTA), Facultad de Ciencias Exactas, Universidad Nacional de La Plata, (1900) La Plata, Buenos Aires, Argentina.

关键词: Tautomerism;    ketones;    mass spectrometry;    theoretical calculations;   

DOI  :  10.3390/i5110294

来源: mdpi

【 摘 要 】

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.

【 授权许可】

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