Mass spectrometry as a tool for the determination of heats of tautomerization of thioamides in the gas phase

Eur. J. Mass Spectrom. 11, 53–64 (2005)
DOI: 10.1255/ejms.691

Mass spectrometry as a tool for the determination of heats of tautomerization of thioamides in the gas phase

P. E. Allegretti, C. B. Milazzo and J. J. P. Furlong^*
LADECOR (UNLP), División Química Orgánica, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Calle 47 & 115, (1900) La Plata, Argentina

ABSTRACT:

Tautomerism of several thioamides has been studied by mass spectrometry. The analysis of the corresponding mass spectra has allowed to assign some fragmentations to specific tautomers and to determine heats of tautomerization through temperature effects and electron energy studies. Experimental determinations are strongly supported by theoretical calculations. AM1 semi-empirical results indicate that the thioamide- thioimidol equilibrium can be studied by mass spectrometry. Besides, additional evidence is obtained regarding tautomerism occurrence between neutral species.

Keywords: heats of tautomerization, thioamides, mass spectrometry, theoretical calculations

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