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Crystal structure of bis(3,5-dichloro-2-hydroxybenzyl)(2-methoxyethyl)amine

The title compound, systematic name 4,4′,6,6′-tetrachloro-2,2′-{[(2-methoxy­ethyl)azanediyl]bis(methylene)}diphenol (C(17)H(17)Cl(4)NO, 1), was prepared via a modified Mannich reaction between 2-meth­oxy­ethyl­amine, 2,4-di­chloro­phenol, and aqueous formaldehyde. The resulting amine bis­(phenol) pr...

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Detalles Bibliográficos
Autores principales: Wile, Bradley M., Griffith, Claire L., Johnson, Adam R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10483550/
https://www.ncbi.nlm.nih.gov/pubmed/37693661
http://dx.doi.org/10.1107/S2056989023006564
Descripción
Sumario:The title compound, systematic name 4,4′,6,6′-tetrachloro-2,2′-{[(2-methoxy­ethyl)azanediyl]bis(methylene)}diphenol (C(17)H(17)Cl(4)NO, 1), was prepared via a modified Mannich reaction between 2-meth­oxy­ethyl­amine, 2,4-di­chloro­phenol, and aqueous formaldehyde. The resulting amine bis­(phenol) provides an inter­esting comparison to related species as a result of the electron-withdrawing substituents on the phenol rings, in combination with similar steric parameters. One of the Cl atoms was modeled as a two-component disorder with partial occupancies of 0.49 (3) and 0.51 (3), while the pendant ether group was modeled as a two-component disorder with partial occupancies of 0.867 (3) and 0.133 (3). A comparison of metrical parameters for the title compound and closely related structures provides insight into the use of these species as ligands to support transition-metal complexes for applications as homogeneous catalysts.