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Conformational analysis and crystal structure of (E)-3-methyl-4-(p-tolyldiazenyl)phenol

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Abstract

The single crystal X-ray diffraction analysis of the title compound, C14H14N2O, reveals that an interesting intermolecular or extended structure (hydrogen-bonded polymeric zigzag chains) is formed by linking its monomer units with O–H···N type intermolecular hydrogen bonds. The compound crystallizes in the monoclinic space group P21/n with a = 5.8151(5) Å, b = 18.106(1) Å, c = 11.515(1) Å  and β = 96.891(7)°. In order to understand better its structural aspects in solid state, quantum chemical (PM3) calculations were performed on a part of the extended structure of the title compound containing ten monomers. To determine in vacuo conformational flexibility of the compound, molecular energy profile of the title compound was obtained with respect to a selected torsional degree of freedom and the pedal angle varied from −180° to +180° in every 10°. The results from the computational study suggest that hydrogen-bonding properties in the crystal lattice is fundamental in determining the crystallographically observed conformation of the title compound.

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Acknowledgment

Hasan Karabıyık would like to thank TÜBİTAK (The Scientific and Technical Research Council of Turkey) for partial financial support.

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Authors and Affiliations

  1. Department of Physics, Dokuz Eylül University, 35160, Buca, İzmir, Turkey

    Hasan Karabıyık

  2. Department of Science Education, Ondokuz Mayıs University, 57000, Sinop, Turkey

    Nazan Ocak İskeleli

  3. Department of Chemistry, Ondokuz Mayıs University, 55139, Samsun, Turkey

    Çiğdem Albayrak & Erbil Ağar

Authors
  1. Hasan Karabıyık
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  2. Nazan Ocak İskeleli
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  3. Çiğdem Albayrak
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  4. Erbil Ağar
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Correspondence to Hasan Karabıyık.

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Karabıyık, H., İskeleli, N.O., Albayrak, Ç. et al. Conformational analysis and crystal structure of (E)-3-methyl-4-(p-tolyldiazenyl)phenol. Struct Chem 18, 87–93 (2007). https://doi.org/10.1007/s11224-006-9130-1

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  • DOI: https://doi.org/10.1007/s11224-006-9130-1

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