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International Journal of Spectroscopy
Volume 2009 (2009), Article ID 408345, 18 pages
Research Article

Spectrometric Study of the Nitrile-Ketenimine Tautomerism

LADECOR (UNLP), División Química Orgánica, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Calle 47 y 115, 1900 La Plata, Argentina

Received 13 October 2008; Revised 17 February 2009; Accepted 8 June 2009

Academic Editor: Craig J. Eckhardt

Copyright © 2009 Hebe Saraví Cisneros et al. 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.


Mass spectrometry is used to evaluate the occurrence of the nitrile-ketenimine tautomerism. Mass spectra of two differently substituted nitriles, ethyl-4,4-dicyano-3-methyl-3-butenoate and diethyl-2-cyano-3-methyl-2-pentenodiate are examined looking for common mass spectral behaviors. Ion fragmentation assignments for specific tautomers allow to predict the presence of the corresponding structures. Additionally, the mass spectrum and nuclear magnetic resonance spectra of ethyl-4,4-dicyano-2,2-diethyl-3-methyl-3-butenoate and that of the corresponding amination product support the occurrence of the ketenimine tautomer in the equilibrium.