(E)-1-[2-(3,4-Dimethylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate

Abstract

The title zwitterion, C18H16N2O, features an intramolecular N—H...O hydrogen bond. The dimethylbenzene ring is rotationally disordered about the N—C bond over two adjacent orientations in a 0.75:0.25 ratio. The dihedral angle between the major orientation of the benzene ring and the naphthalene ring system is 6.06 (2)°. In the crystal, aromatic π–π stacking occurs [shortest centroid–centroid distance = 3.574 (3) Å] and C—H...O interactions are also observed.

Tautomerization of diazene<=>hydrazine via single proton tautomerization, spectral, XRD/HSA-interactions, optical and DFT/TD-DFT of new hydrazine ligand

“…Azo-ligands are very crucial in the field of dyes and advanced materials [1]. They are very coloured and have long been used as pigments [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18]. They have many practical applications such as the coloring of diverse materials, the dyeing of textile fibers, colored polymers and plastics, medicinal-biological, and advanced applications in organic syntheses [2][3][4][5].…”

“…Their optical properties depend on spectroscopic properties and their crystallographic arrangements [14][15]. In general, 1-phenylazo-2-naphthol can coexist in azo and hydrazone tautomer forms [16][17][18]. Hydrazone form have an ionic intra-molecular hydrogen bond (N+-H• • •O -) and their N + -H bond lengths are longer than the standard interatomic [19].…”