, Volume 41, Issue 7, pp 944-951
Date: 02 Mar 2011

Synthesis and Structural Characterization of (Z)-3-[(4-Chlorophenylamino) Methylene] Naphthalene-2(3H)-One: An Enol, Keto or Zwitterionic Tautomer?

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Abstract

The structure of the title compound was determined using X-ray crystallography at both 173 and 293 K. The molecular structure and packing did not change significantly with temperature and a disordered structure was identified comprising a keto and enol tautomeric form. Analysis of the bond lengths in the vicinity of the C=O group suggested the keto form was predominantly in its zwitterionic form structure. 1H NMR spectroscopy showed the presence of a single compound in solution with two diagnostic doublets demonstrating the compound had an NH group next to a CH group resembling the zwitterionic form of the compound.

Graphical Abstract