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The two title molecules, both C(15)H(14)N(2)O(3), are roughly planar and display a trans conformation with respect to the -N=N- double bond, as found for other diazene derivatives. In both compounds, there are intramolecular O-H.O hydrogen bonds and the crystal packing is governed by weak intermolecular C-H.O hydrogen bonds and pi-pi stacking.

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The crystal and molecular structures of an o-hydroxy Schiff base derivative, (E)-2-ethoxy-6-[(2-methoxyphenylimino)methyl]phenol, have been determined by single crystal X-ray diffraction analyses at 296 and 100 K. The results from temperature-dependent structural analysis regarding the tautomeric equilibrium of the compound were interpreted with the aid of quantum chemical calculations. To clarify the tautomerization process and its effects on the molecular geometry, the gasphase geometry optimizations of two possible tautomers of the title molecule, its OH and NH form, were achieved using DFT calculations with B3LYP method by means of 6-31 ? G(d,p) basis set. In order to describe the potential barrier belonging to the phenolic proton transfer, nonadiabatic Potential Energy Surface (PES) scan was performed based on the optimized geometry of the OH tautomeric form by varying the redundant internal coordinate, O-H bond distance. The Harmonic Oscillator Model of Aromaticity (HOMA) indices were calculated in every step of the scan process so as to express the deformation in the aromaticities of principal molecular moieties of the compound. The results show that there is a dynamic equilibrium between the aromaticity level of phenol and chelate ring and furthermore p-electron coupling affecting overall molecule of the title compound. Charge transfer from phenol ring to pseudo-aromatic chelate ring increases with increasing temperature, whereas p-electron transfer from chelate ring to anisole ring is decreased as temperature increases. The most strength intramolecular H-bonds are observed for conformers close to transition state.

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The title compounds, (E)-2-[(2-bromophenyl)iminomethyl]-4-methoxyphenol, C(14)H(12)BrNO(2), (I), (E)-2-[(3-bromophenyl)iminomethyl]-4-methoxyphenol, C(14)H(12)BrNO(2), (II), and (E)-2-[(4-bromophenyl)iminomethyl]-4-methoxyphenol, C(14)H(12)BrNO(2), (III), adopt the phenol-imine tautomeric form. In all three structures, there are strong intramolecular O-H...N hydrogen bonds. Compound (I) has strong intermolecular hydrogen bonds, while compound (III) has weak intermolecular hydrogen bonds. In addition to these intermolecular interactions, C-H...pi interactions in (I) and (III), and pi-pi interactions in (I), play roles in the crystal packing. The dihedral angles between the aromatic rings are 15.34 (12), 6.1 (3) and 39.2 (14) degrees for (I), (II) and (III), respectively.

The title 4,4'-disubstituted diphenyl-1,3-triazines, C14H15N3, (I), C12H9ClFN3, (II), and C13H12FN3, (III), each contain a triazene group (-N=N-NH-) having an extended conformation. The dihedral angles between the two benzene rings in (I), (II) and (III) are 4.3, 3.4 and 6.5 degrees , respectively. The molecules are almost entirely planar, with maximum deviations from the mean planes of 0.1087 (2), -0.1072 (7) and 0.1401 (3) A, respectively. In each compound, the molecules are linked by N-H...N hydrogen bonds to form chains and pack similarly in the crystal structures.

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