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N-(Phenyl)-2-benzoylethylamine (I), N-(4-chlorophenyl)-2-benzoylethylamine (II), and N-(2-chlorophenyl)-2-benzoylethylamine hydrazone (III) were synthesized in the crystalline state. The heating of ethanolic solutions of compound III at reflux gave dimeric bis[3-(о-chlorophenyl)-1-phenylaminopropyl]diazene (IV). The crystal and molecular structures of compounds II and IV were determined by X-ray diffraction. In the crystal of II, the molecules are packed in stacks in a head-to-head fashion stabilized by intermolecular hydrogen bonds involving carbonyl oxygen atoms and hydrogen atoms at nitrogen. Compound IV is composed of two independent bis[3-(о-chlorophenyl)-1-phenylaminopropyl]diazene molecules as structural units. Each structural unit is a centrosymmetric dimer. There are no hydrogen bonds in compound IV. Acid–base equilibrium reactions were studied by spectrophotometric titration. The protonation constants are 4.68 ± 0.14 for I and 4.11 ± 0.13 for II.
Crystallography Reports – Springer Journals
Published: Jan 25, 2020
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