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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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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
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author Wile, Bradley M.
Griffith, Claire L.
Johnson, Adam R.
author_facet Wile, Bradley M.
Griffith, Claire L.
Johnson, Adam R.
author_sort Wile, Bradley M.
collection PubMed
description 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.
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spelling pubmed-104835502023-09-08 Crystal structure of bis(3,5-dichloro-2-hydroxybenzyl)(2-methoxyethyl)amine Wile, Bradley M. Griffith, Claire L. Johnson, Adam R. Acta Crystallogr E Crystallogr Commun Research Communications 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. International Union of Crystallography 2023-08-04 /pmc/articles/PMC10483550/ /pubmed/37693661 http://dx.doi.org/10.1107/S2056989023006564 Text en © Wile et al. 2023 https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Research Communications
Wile, Bradley M.
Griffith, Claire L.
Johnson, Adam R.
Crystal structure of bis(3,5-dichloro-2-hydroxybenzyl)(2-methoxyethyl)amine
title Crystal structure of bis(3,5-dichloro-2-hydroxybenzyl)(2-methoxyethyl)amine
title_full Crystal structure of bis(3,5-dichloro-2-hydroxybenzyl)(2-methoxyethyl)amine
title_fullStr Crystal structure of bis(3,5-dichloro-2-hydroxybenzyl)(2-methoxyethyl)amine
title_full_unstemmed Crystal structure of bis(3,5-dichloro-2-hydroxybenzyl)(2-methoxyethyl)amine
title_short Crystal structure of bis(3,5-dichloro-2-hydroxybenzyl)(2-methoxyethyl)amine
title_sort crystal structure of bis(3,5-dichloro-2-hydroxybenzyl)(2-methoxyethyl)amine
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10483550/
https://www.ncbi.nlm.nih.gov/pubmed/37693661
http://dx.doi.org/10.1107/S2056989023006564
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