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Synthesis, characterization, crystal structure and theoretical studies of new chiral Schiff base (E)-4-hydroxy[(1-phenylethyl)iminomethyl]benzyne

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Abstract

New chiral Schiff-base (E)-4-hydroxy[(1-phenylethyl)iminomethyl]benzyne (1) was synthesized through the condensation of 4-hydroxybenzaldehyde and 1-phenylethylamine in methanol at ambient temperature and characterized by elemental analyses (CHN), FT-IR, and 1H NMR spectroscopy. The crystal structure of the title compound was determined from single-crystal X-ray diffraction study. The title compound crystallizes in the orthorhombic space group P212121 with unit cell parameters: a = 5.9332(2), b = 10.0198(3), c = 20.9678(6) Ǻ, V = 1246.52(7) Ǻ3, and Z = 4. The molecular geometry of the title compound has been calculated using the density functional method (B3LYP) with 6-31G basis set and compared with the experimental data. Calculated results show that density functional theory can well reproduce the structure of the title compound. In the gas phase, the two conformers (cis and trans) for the title compound were found, with the trans isomer being the most stable one.

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Acknowledgments

We acknowledge the Golestan University (GU) for partial support of this study and the institutional research plan No. AVOZ10100521 of the Institute of Physics and the project 202/07/J007 of the Grant Agency of the Czech Republic.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Golestan University, Gorgan, Iran

    Aliakbar Dehno Khalaji, Mohammad Gholinejad & Sepideh Maghsodlou Rad

  2. School of Chemistry, Damghan University, P.O. Box 36715-364, Damghan, Iran

    Gholamhossein Grivani

  3. Institute of Physics of the ASCR, v.v.i, Na Slovance 2, 182 21, Prague 8, Czech Republic

    Karla Fejfarova & Michal Dusek

Authors
  1. Aliakbar Dehno Khalaji
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  2. Mohammad Gholinejad
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  3. Sepideh Maghsodlou Rad
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  4. Gholamhossein Grivani
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  5. Karla Fejfarova
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Correspondence to Aliakbar Dehno Khalaji.

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Khalaji, A.D., Gholinejad, M., Rad, S.M. et al. Synthesis, characterization, crystal structure and theoretical studies of new chiral Schiff base (E)-4-hydroxy[(1-phenylethyl)iminomethyl]benzyne. Res Chem Intermed 41, 1635–1645 (2015). https://doi.org/10.1007/s11164-013-1299-5

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