Synthesis, molecular and electronic properties, and crystal structure of two novel potent perfluorophenylhydrazone derivatives, 1-((5-nitrothiophen-2-yl)methylene)-2-(perfluorophenyl) hydrazine, and 1-((5-nitrofuran-2-yl)methylene)-2-(perfluorophenyl) hydrazine

Two novel potent perfluorophenylhydrazone derivatives, 1-((5-nitrothiophen-2-yl)methylene)-2-(per- fluorophenyl)hydrazine, ( I ), and 1-((5-nitrofuran-2-yl)methylene)-2-(perfluorophenyl) hydrazine, ( II ), are introduced, with suggested improvement by further design. Their multitarget structures and features have been combined to create potential AD therapeutics. Crystals ( I ) and ( II ) are molecules with two rings and a hydrazone part at the centre of the molecule. They were synthesised and characterised using elemental and spectroscopic ( 1 H-NMR) analyses and their crystal structures were determined using the single-crystal X-ray diffraction method. The structures crystallise in the monoclinic space group with Z = 2 and Z = 4 molecules per unit cell. Compound ( I ) crystallises as a dimer in the non-centrosymmetric space group, while compound ( II ) crystallises as a racemate in the centrosymmetric space group. The “absolute configuration and conformation for bond values” were not derived from anomalous dispersion (rmad). The crystal structures reveal diverse non-covalent interactions such as intra- and inter-hydrogen bonding, π-ring — π-ring, C—H — π-ring interactions. The expected stereochemistry of hydrazone atoms C7, N2, and N1 was confirmed for compounds ( I ) and ( II ). Both molecules possess a “boat conformation” resembling a 6-membered ring. Results of the single crystal studies were reproduced using the Hirshfeld surface analysis, Gaussian software, and QTAIM contour mapping.