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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.

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Acknowledgments

This research was funded by a Program Grant from the National Health and Medical Research Council of Australia. We acknowledge the QNN for granting us access to the 900 Hz NMR spectrometer. The authors would like to thank Dr. Ekatarina Strounina for acquiring the 13C solid state NMR spectra.

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Authors and Affiliations

  1. Centre for Advanced Imaging, The University of Queensland, Brisbane, 4072, Australia

    T. K. Venkatachalam, Gregory K. Pierens & David C. Reutens

  2. School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, 4072, Australia

    Paul V. Bernhardt

  3. Queensland Brain Institute, The University of Queensland, Brisbane, 4072, Australia

    T. K. Venkatachalam, Luke Hammond & David C. Reutens

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  1. T. K. Venkatachalam
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  2. Gregory K. Pierens
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  3. Paul V. Bernhardt
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Correspondence to T. K. Venkatachalam.

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Venkatachalam, T.K., Pierens, G.K., Bernhardt, P.V. et al. Synthesis and Structural Characterization of (Z)-3-[(4-Chlorophenylamino) Methylene] Naphthalene-2(3H)-One: An Enol, Keto or Zwitterionic Tautomer?. J Chem Crystallogr 41, 944–951 (2011). https://doi.org/10.1007/s10870-011-0022-x

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  • DOI: https://doi.org/10.1007/s10870-011-0022-x

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