RESUMEN

In this work, the azo dye, (E)-1-[5-(3,4-dimethylphenyldiazenyl)-2-hydroxyphenyl]ethanone, has been synthesized and characterized by IR, and X-ray single-crystal determination. In the theoretical calculations, the stable structure geometry of the isolated molecule in gas phase was investigated under the framework of the density functional theory (B3LYP) with 6-31G (d, p). To designate lowest energy molecular conformation of the title molecule, the selected torsion angle was varied every 10° and the molecular energy profile was calculated from -180° to +180°. Besides, molecular electrostatic potential (MEP), frontier molecular orbitals (FMO) analysis, and thermodynamic properties were described from the computational process. In addition to these calculations, we were investigated solvent effects on the nonlinear optical properties (NLO) of the title compound.

Asunto(s)

Compuestos Azo/química , Colorantes/química , Compuestos Azo/síntesis química , Colorantes/síntesis química , Cristalografía por Rayos X , Modelos Moleculares , Conformación Molecular , Espectroscopía Infrarroja por Transformada de Fourier , Termodinámica

RESUMEN

The mol-ecular geometry of the title compound, C(17)H(18)N(2)O(2), displays an E configuration with respect to the azo group. The dihedral angle between the aromatic rings is 10.39 (4)°. In the mol-ecule, an intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif.

RESUMEN

Theere are two independent mol-ecules in the asymmetric unit of the title compound, C(14)H(11)FN(2)O(2), each with a trans configuration with respect to the azo double bond. The dihedral angle between the aromatic rings is 17.21 (2)° in one mol-ecule and 19.06 (2)° in the other. Each of the independent mol-ecules has an intra-molecular O-H⋯O hydrogen bond. In the crystal, mol-ecules are stacked along [100].

RESUMEN

The mol-ecule of the title compound, C(16)H(17)NO(2), adopts the phenol-imine tautomeric form with a strong intra-molecular O-H⋯N hydrogen bond and an E conformation with respect to the azomethine C=N bond. The dihedral angle between the aromatic rings is 21.23 (9)°. The ethyl group is disordered over two orientations with occupancies of 0.598 (6) and 0.402 (6). In the crystal, the mol-ecules are linked into chains along the b axis by C-H⋯π inter-actions.

RESUMEN

The mol-ecule of the title compound, C(15)H(15)NO(2), crystallizes in a zwitterionic form, and displays an E configuration about the C=N bond. The dihedral angle between the two aromatic rings is 5.59 (6)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, pairs of mol-ecules are linked into centrosymmetric R(2) (2)(10) dimers by pairs of O-H⋯O hydrogen bonds. Aromatic π-π inter-actions are observed between the benzene rings of adjacent dimers [centroid-centroid distance = 3.4808 (7) Å].

RESUMEN

The title compound, C(15)H(14)N(2)O(2), an azo dye, displays a trans configuration with respect to the N=N bridge. The dihedral angle between the aromatic rings is 0.18 (14)°. There is a strong intra-molecular O-H⋯O hydrogen bond. Geometrical parameters, determined using X-ray diffraction techniques, are compared with those calculated by density functional theory (DFT), using hybrid exchange-correlation functional, B3LYP and semi-empirical (PM3) methods.

RESUMEN

The title compound, C(16)H(17)NO(2), crystallizes with three crystallographically independent zwitterionic mol-ecules in the asymmetric unit which differ significantly in the orientations of the propyl side chains. The dihedral angles between the two benzene rings in the three mol-ecules are 6.17 (7), 6.75 (7) and 23.67 (7)°, respectively. In each independent mol-ecule, an intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, each independent mol-ecule exists as part of an O-H⋯O hydrogen-bonded centrosymmetric R(2) (2)(10) dimer.

RESUMEN

The title compound, C(13)H(10)ClNO(2), exists in the phenol-imine form in the crystal, and the aromatic rings are oriented at a dihedral angle of 2.82 (9)°. An intra-molecular O-H⋯N hydrogen bond results in the formation of a planar six-membered ring. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into chains.

RESUMEN

In the mol-ecule of the title compound, C(23)H(17)N(3)O(2), the methoxy-phenyl ring is oriented at dihedral angles of 13.34 (12) and 88.83 (12)° with respect to the methyl-phenyl and phthalonitrile rings, respectively; the dihedral angle between methyl-phenyl and phthalonitrile rings is 89.67 (10)°. In the crystal structure, weak inter-molecular C-H⋯N inter-actions link mol-ecules into chains. A weak C-H⋯π inter-action is also found..