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

Crystal and Molecular Structures and Acid–Base Equilibria of... 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Crystallography Reports Springer Journals

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

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Publisher
Springer Journals
Copyright
Copyright © Pleiades Publishing, Inc. 2020
ISSN
1063-7745
eISSN
1562-689X
DOI
10.1134/S1063774520010125
Publisher site
See Article on Publisher Site

Abstract

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.

Journal

Crystallography ReportsSpringer Journals

Published: Jan 25, 2020

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