Related Experiment Video
Updated: Jul 16, 2025

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
Published on: February 15, 2016
Crystal structure of bis(3,5-dichloro-2-hydroxybenzyl)(2-methoxyethyl)amine
Bradley M Wile1, Claire L Griffith1, Adam R Johnson2
1The Donald J. Bettinger Department of Chemistry and Biochemistry, The School of Science, Technology, and Mathematics, Ohio Northern University, 525 S. Main Street, Ada, OH 45810, USA.
A novel tetrachlorinated bisphenol ligand was synthesized using a modified Mannich reaction. This compound
Area of Science:
- Organic Chemistry
- Coordination Chemistry
- Catalysis
Background:
- Bisphenol compounds are versatile ligands in coordination chemistry.
- Electron-withdrawing substituents on phenol rings can influence ligand properties.
- Mannich reactions are effective for synthesizing substituted phenols.
Purpose of the Study:
- To synthesize and characterize a novel tetrachlorinated bisphenol compound.
- To investigate the structural features and potential applications of the synthesized ligand.
- To compare the properties of the new ligand with related structures.
Main Methods:
- Modified Mannich reaction involving 2-methoxy-ethyl-amine, 2,4-dichloro-phenol, and formaldehyde.
- Crystallographic analysis to determine molecular structure and disorder.
- Metrical parameter analysis for comparison with related compounds.
Main Results:
- Successful synthesis of 4,4',6,6'-tetrachloro-2,2'-{[(2-methoxy-ethyl)azanediyl]bis(methylene)}diphenol.
- Identification of two-component disorder in chlorine atom and ether group.
- Detailed comparison of structural parameters with analogous bisphenol ligands.
Conclusions:
- The synthesized tetrachlorinated bisphenol serves as a valuable ligand for transition metal complexes.
- Structural insights gained can guide the design of homogeneous catalysts.
- The electron-withdrawing chlorine substituents and steric factors impact ligand behavior.
Related Concept Videos
Structure of Amines
Structures of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the...
Aldehydes and Ketones with Amines: Enamine Formation Mechanism
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Acid Halides to Amides: Aminolysis
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
Nomenclature of Secondary and Tertiary Amines

