European Journal of Mass Spectrometry - Abstract of Mass spectrometry of β-ketoesters. Some evidence of their tautomerism

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European Journal of Mass Spectrometry
Volume 12 Issue 5, Pages 317–330 (2006)
doi: 10.1255/ejms.819

Mass spectrometry of β-ketoesters. Some evidence of their tautomerism

Patricia E. Allegretti,^a Eduardo A. Castro^b and Jorge J. P. Furlong^a,*
^aLaboratorio 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
^bINIFTA (UNLP-CONICET-CIC), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Diagonal 113 y 64, Suc. 4, C. C. 16, (1900) La Plata, Buenos Aires, Argentina

ABSTRACT:

Mass spectrometric evidence of tautomerism is reported for β-ketoesters. The analysis of the corresponding mass spectra has allowed specific assignment of fragment ions to tautomers. The predictive value of this methodology is supported by the influence of substitution pattern of these compounds on these equilibria. Experimental data are strongly supported by AM1 semiempirical calculations indicating that mass spectrometry could be resourced as a tool for the investigation of tautomerism of neutral species in the gas phase.

Keywords: tautomerism, β- Ketoesters, mass spectrometry, theoretical calculations

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