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Synthesis, Crystallographic and Spectral Studies of 3-(4-(Phenylamino) Phenylamino)Cyclohex-2-Enone

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Abstract

The title compound, 3-(4-(phenylamino)phenylamino)cyclohex-2-enone, β-enaminone of 1,3-cyclohexanedione and p-amino diphenylamine (C18H18N2O) was prepared and characterized by 1H-NMR, 13C-NMR, Elemental analysis and IR spectroscopy as well as single crystal X-ray diffraction. These results indicate the predominance of the keto-enol tautomerism. Molecular conformation around the central disubstituted benzene ring is affected by the tautomerism and two steric effects between side molecular groups and mono substituted benzene ring. Electron delocalizations due to these effects have been observed in the molecular structure, the structure being stabilized by some intermolecular hydrogen bonds.

Graphical Abstract

The title compound, 3-(4-(phenylamino)phenylamino)cyclohex-2-enone, was synthesized by the treatment of 1,3-cyclohexanedione with p-amino diphenylamine and its crystal structure determined. According to 1H and 13C NMR data the newly prepared β-enaminone compound exists as the E-s-E-s-Z conformation. This is consistent with X-ray crystallographic study.

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Scheme 1
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Acknowledgments

This work was supported financially by Hacettepe University (Research Center Office/Projects No: 01.02.602.002 and 05A601009).

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Authors and Affiliations

  1. Faculty of Science, Department of Chemistry, Hacettepe University, 06800, Beytepe-Ankara, Turkey

    Mahir Timur, Hülya Şenöz & Nazan Tunoğlu

  2. Faculty of Science and Art, Department of Physics, Dicle University, 21280, Diyarbakır, Turkey

    Gülten Kavak

  3. Faculty of Engineering, Department of Physics Engineering, Hacettepe University, 06800, Beytepe-Ankara, Turkey

    Semra İde

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  1. Mahir Timur
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  2. Gülten Kavak
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  3. Hülya Şenöz
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  4. Semra İde
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  5. Nazan Tunoğlu
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Correspondence to Mahir Timur.

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Timur, M., Kavak, G., Şenöz, H. et al. Synthesis, Crystallographic and Spectral Studies of 3-(4-(Phenylamino) Phenylamino)Cyclohex-2-Enone. J Chem Crystallogr 40, 376–380 (2010). https://doi.org/10.1007/s10870-009-9664-3

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