Abstract
Crystals of naphthol azo compound of 4-aminoantipyrine, C21H18N4O2 have been grown by slow evaporation method from DMF at room temperature. The grown crystals were characterized by FT-IR, UV-Vis, 13C and 1H NMR spectra. The molecular structure was analyzed by single crystal X-ray diffraction data. The compound 4-[(E)-(3-hydroxy naphthalene-2-yl)diazenyl]-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one crystallizes in the monoclinic P21/c space group with cell dimensions a = 18.7902 (12) Å, b = 6.4128 (5) Å, c = 14.7923 (11) Å and β = 91.229 (2)°. The solvatochromism of dye was evaluated with respect to the wavelength of absorption maxima in nine solvents. Due to the presence of intramolecular hydrogen bonding, hydrazone form predominates in most of the polar protic and polar aprotic solvents. The pH effects on the visible absorption spectra of dye was also reported. The fitting of spectroscopic values to solvent parameters and correlate with the Kamlet-Abboud-Taft equation is also highlighted. The title compound exhibits the single stranded DNA cleaving activity with pUC18 DNA in tris-base buffer (pH 8).
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