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Dimethyl 4,5-dichlorophthalate
While endeavoring to synthesize new chlorinated ligands for ruthenium-based metathesis catalysts, the title compound dimethyl 4,5-dichlorophthalate, C(10)H(8)Cl(2)O(4), was prepared from commercially available 4,5-dichlorophthalic acid in ∼77% yield. The title molecule, which also finds utility...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9462297/ https://www.ncbi.nlm.nih.gov/pubmed/36340982 http://dx.doi.org/10.1107/S2414314621010439 |
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author | Hickstein, Daniel D. Reinheimer, Eric W. Johnson, Adam R. O’Leary, Daniel J. |
author_facet | Hickstein, Daniel D. Reinheimer, Eric W. Johnson, Adam R. O’Leary, Daniel J. |
author_sort | Hickstein, Daniel D. |
collection | PubMed |
description | While endeavoring to synthesize new chlorinated ligands for ruthenium-based metathesis catalysts, the title compound dimethyl 4,5-dichlorophthalate, C(10)H(8)Cl(2)O(4), was prepared from commercially available 4,5-dichlorophthalic acid in ∼77% yield. The title molecule, which also finds utility as a precursor molecule for the synthesis of drugs used in the treatment of Alzheimer’s disease, shows one carbonyl-containing methyl ester moiety lying nearly co-planar with the chlorine-derivatized aromatic ring while the second methyl ester shows a significant deviation of 101.05 (12)° from the least-squares plane of the aromatic ring. Within the crystal, structural integrity is maintained by the concerted effects of electrostatic interactions involving the electron-deficient carbonyl carbon atom and the electron-rich aromatic ring along the a-axis direction and C—H⋯O hydrogen bonds between neighboring molecules parallel to b. [Image: see text] |
format | Online Article Text |
id | pubmed-9462297 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-94622972022-11-04 Dimethyl 4,5-dichlorophthalate Hickstein, Daniel D. Reinheimer, Eric W. Johnson, Adam R. O’Leary, Daniel J. IUCrdata Data Reports While endeavoring to synthesize new chlorinated ligands for ruthenium-based metathesis catalysts, the title compound dimethyl 4,5-dichlorophthalate, C(10)H(8)Cl(2)O(4), was prepared from commercially available 4,5-dichlorophthalic acid in ∼77% yield. The title molecule, which also finds utility as a precursor molecule for the synthesis of drugs used in the treatment of Alzheimer’s disease, shows one carbonyl-containing methyl ester moiety lying nearly co-planar with the chlorine-derivatized aromatic ring while the second methyl ester shows a significant deviation of 101.05 (12)° from the least-squares plane of the aromatic ring. Within the crystal, structural integrity is maintained by the concerted effects of electrostatic interactions involving the electron-deficient carbonyl carbon atom and the electron-rich aromatic ring along the a-axis direction and C—H⋯O hydrogen bonds between neighboring molecules parallel to b. [Image: see text] International Union of Crystallography 2021-10-13 /pmc/articles/PMC9462297/ /pubmed/36340982 http://dx.doi.org/10.1107/S2414314621010439 Text en © Hickstein et al. 2021 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 | Data Reports Hickstein, Daniel D. Reinheimer, Eric W. Johnson, Adam R. O’Leary, Daniel J. Dimethyl 4,5-dichlorophthalate |
title | Dimethyl 4,5-dichlorophthalate |
title_full | Dimethyl 4,5-dichlorophthalate |
title_fullStr | Dimethyl 4,5-dichlorophthalate |
title_full_unstemmed | Dimethyl 4,5-dichlorophthalate |
title_short | Dimethyl 4,5-dichlorophthalate |
title_sort | dimethyl 4,5-dichlorophthalate |
topic | Data Reports |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9462297/ https://www.ncbi.nlm.nih.gov/pubmed/36340982 http://dx.doi.org/10.1107/S2414314621010439 |
work_keys_str_mv | AT hicksteindanield dimethyl45dichlorophthalate AT reinheimerericw dimethyl45dichlorophthalate AT johnsonadamr dimethyl45dichlorophthalate AT olearydanielj dimethyl45dichlorophthalate |