Crystallographic and conformational analysis of (E)-2-isopropyl-4-(p-tolyldiazenyl)phenol
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Abstract
The molecular and crystal structures of the title compound, C16H18N2O, were characterized and determined by single crystal X-ray diffraction method in addition to spectroscopic means such as IR, UV–VIS and 1H NMR. The compound crystallizes in orthorhombic space group P bca, with a = 9.3350(5) Å, b = 23.4878(13) Å, c = 26.5871(12) Å, Z = 16, D calc. = 1.1591(1) g/cm3, μ (MoKα) = 0.073 mm−1. Monomers of the compound in the crystal structure are linked into C(7) and C(8) chains generated by translation along the [1 0 0] direction with the aid of O–H···N type H-bonds which serve to the stabilization of periodic organization of the molecules beside major and minor component in the disordered azo fragment. In order to describe conformational flexibility and the crystal packing effects on the molecular conformation, potential barriers regarding the rotation along both Ar–N bonds were calculated by varying the related torsional degrees of freedom in every 10° ranging from −180° to +180° via quantum chemical calculations at DFT/B3LYP level.
Keywords
Azo benzene DFT/B3LYP Conformational analysis Crystal structureNotes
Acknowledgments
Hasan Karabıyık would like to thank TÜBİTAK (The Scientific and Technical Research Council of Turkey) for partial financial support. In addition, the authors wish to acknowledge Ondokuz Mayıs University for the use of the STOE IPDS 2 diffractometer purchased under Grants F.279 and F.377.
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