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Spectroscopic Studies and Crystal Structure of (Z)-6-[(2-hydroxyphenylamino)methylene]-2-methoxycyclohexa-2,4-dienone

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Abstract

The Schiff base (Z)-6-[(2-hydroxyphenylamino)methylene]-2-methoxycyclohexa-2,4-dienone has been synthesized from the reaction of 2-aminophenol with 2-hydroxy-3-methoxybenzaldehyde. The title compound has been characterized by elemental analysis, FT-IR, 1H-NMR, 13C-NMR and UV–Visible techniques. The structure of the title compound also was determined crystallographically. The crystal structure has been solved by direct methods and refined by full-matrix least squares. The title compound crystallize in the monoclinic space group P21/c with a = 10.438(1), b = 8.851(1), c = 12.746(1) Å, β = 95.72(1)°, V = 1171.7(2) Å3, D x  = 1.379 g cm−3, respectively (R1 = 0.0522 and wR2 = 0.126 for 1442 reflections [I > 2σ(I)]).

Index Abstract

N-salicylideneaniline derivatives have been shown to exist as tautomeric forms due to intramolecular proton shifts between the phenol-oxygen and the imine-nitrogen, via intramolecular hydrogen bonding O–H···N or O···H–N.

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Authors and Affiliations

  1. Department of Physics, Faculty of Science, Ankara University, Tandoğan, 06100, Ankara, Turkey

    Hüseyin Ünver

  2. Department of Chemistry, Faculty of Science and Arts, Çanakkale Onsekiz Mart University, 17100, Canakkale, Turkey

    Mustafa Yıldız

  3. Department of Natural Sciences, Faculty of Education, Çanakkale Onsekiz Mart University, 17100, Canakkale, Turkey

    Aşkın Kiraz

  4. Department of Engineering Physics, Faculty of Engineering, Hacettepe University, Beytepe, Ankara, Turkey

    Özen Özgen

Authors
  1. Hüseyin Ünver
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  2. Mustafa Yıldız
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  3. Aşkın Kiraz
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  4. Özen Özgen
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Correspondence to Hüseyin Ünver.

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Ünver, H., Yıldız, M., Kiraz, A. et al. Spectroscopic Studies and Crystal Structure of (Z)-6-[(2-hydroxyphenylamino)methylene]-2-methoxycyclohexa-2,4-dienone. J Chem Crystallogr 39, 17–23 (2009). https://doi.org/10.1007/s10870-008-9412-0

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  • DOI: https://doi.org/10.1007/s10870-008-9412-0

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