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 (C17H17Cl4NO, 1), was prepared via a modified Mannich reaction between 2-methoxyethylamine, 2,4-dichlorophenol, and aqueous formaldehyde. The resulting amine bis(phenol) provides an int...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2023-09-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989023006564 |
| _version_ | 1797690654783963136 |
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| author | Bradley M. Wile Claire L. Griffith Adam R. Johnson |
| author_facet | Bradley M. Wile Claire L. Griffith Adam R. Johnson |
| author_sort | Bradley M. Wile |
| collection | DOAJ |
| description | The title compound, systematic name 4,4′,6,6′-tetrachloro-2,2′-{[(2-methoxyethyl)azanediyl]bis(methylene)}diphenol (C17H17Cl4NO, 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. |
| first_indexed | 2024-03-12T02:02:26Z |
| format | Article |
| id | doaj.art-a8af4dca0e8d4341816f6f693e095226 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-03-12T02:02:26Z |
| publishDate | 2023-09-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-a8af4dca0e8d4341816f6f693e0952262023-09-07T10:28:24ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902023-09-0179978278510.1107/S2056989023006564zl5047Crystal structure of bis(3,5-dichloro-2-hydroxybenzyl)(2-methoxyethyl)amineBradley M. Wile0Claire L. Griffith1Adam R. Johnson2The 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, USAThe 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, USAHarvey Mudd College, Chemistry, 301 Platt Blvd., Claremont, CA 91711, USAThe title compound, systematic name 4,4′,6,6′-tetrachloro-2,2′-{[(2-methoxyethyl)azanediyl]bis(methylene)}diphenol (C17H17Cl4NO, 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.http://scripts.iucr.org/cgi-bin/paper?S2056989023006564crystal structurephenolamineetheraminebis(phenol) |
| spellingShingle | Bradley M. Wile Claire L. Griffith Adam R. Johnson Crystal structure of bis(3,5-dichloro-2-hydroxybenzyl)(2-methoxyethyl)amine Acta Crystallographica Section E: Crystallographic Communications crystal structure phenol amine ether aminebis(phenol) |
| 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 | crystal structure phenol amine ether aminebis(phenol) |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989023006564 |
| work_keys_str_mv | AT bradleymwile crystalstructureofbis35dichloro2hydroxybenzyl2methoxyethylamine AT clairelgriffith crystalstructureofbis35dichloro2hydroxybenzyl2methoxyethylamine AT adamrjohnson crystalstructureofbis35dichloro2hydroxybenzyl2methoxyethylamine |