Crystal and Molecular Structures and Acid–Base Equilibria of N-(4-Chlorophenyl)-2-Benzoylethylamine and Bis[3-(o-Chlorophenyl)-1-Phenylaminopropyl]diazene

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-phenylamin...

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Bibliographic Details
Published in:Crystallography reports 2020, Vol.65 (1), p.48-52
Main Authors: Kovalchukova, O. V., Stash, A. I., Strashnova, S. B., Polyanskaya, N. A.
Format: Article
Language:English
Subjects:
Acid base equilibrium
Carbonyls
Chemical bonds
Crystal structure
Crystallography and Scattering Methods
Crystals
Dimers
Hydrazones
Hydrogen atoms
Hydrogen bonds
Molecular structure
Nitrogen
Oxygen atoms
Physics
Physics and Astronomy
Protonation
Spectrophotometry
Structure of Organic Compounds
Titration
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Summary: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 .
ISSN:1063-7745
1562-689X
DOI:10.1134/S1063774520010125