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Crystal structure of 2,4,6-trimethylbenzoic anhydride
The title compound, C(20)H(22)O(3), was formed in the reaction between 2,4,6-trimethylbenzoic acid and N,N-diisopropylethylamine in the presence of 1,3-dichloro-1,3-bis(dimethylamino)propenium hydrogen dichloride, and was recrystallized from diethyl ether solution. It is the first exclusiv...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2017
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5683502/ https://www.ncbi.nlm.nih.gov/pubmed/29152362 http://dx.doi.org/10.1107/S2056989017014670 |
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author | Land, Michael A. Robertson, Katherine N. Clyburne, Jason A. C. |
author_facet | Land, Michael A. Robertson, Katherine N. Clyburne, Jason A. C. |
author_sort | Land, Michael A. |
collection | PubMed |
description | The title compound, C(20)H(22)O(3), was formed in the reaction between 2,4,6-trimethylbenzoic acid and N,N-diisopropylethylamine in the presence of 1,3-dichloro-1,3-bis(dimethylamino)propenium hydrogen dichloride, and was recrystallized from diethyl ether solution. It is the first exclusively alkyl-substituted benzoic anhydride to have been structurally characterized. The asymmetric unit consists of a half molecule, the other half of which is generated by twofold rotation symmetry; the dihedral angle between the symmetry-related aromatic rings is 54.97 (3)°. The geometric parameters of the aromatic ring are typical of those for 2,4,6-trimethylphenyl substituted groups. The C=O and C—O bond lengths are 1.1934 (12) and 1.3958 (11) Å, respectively, and the angle between these three atoms (O=C—O) is 121.24 (9)°. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds and C—H⋯π interactions. The packing features wavy chains that extend parallel to [001]. |
format | Online Article Text |
id | pubmed-5683502 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-56835022017-11-17 Crystal structure of 2,4,6-trimethylbenzoic anhydride Land, Michael A. Robertson, Katherine N. Clyburne, Jason A. C. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(20)H(22)O(3), was formed in the reaction between 2,4,6-trimethylbenzoic acid and N,N-diisopropylethylamine in the presence of 1,3-dichloro-1,3-bis(dimethylamino)propenium hydrogen dichloride, and was recrystallized from diethyl ether solution. It is the first exclusively alkyl-substituted benzoic anhydride to have been structurally characterized. The asymmetric unit consists of a half molecule, the other half of which is generated by twofold rotation symmetry; the dihedral angle between the symmetry-related aromatic rings is 54.97 (3)°. The geometric parameters of the aromatic ring are typical of those for 2,4,6-trimethylphenyl substituted groups. The C=O and C—O bond lengths are 1.1934 (12) and 1.3958 (11) Å, respectively, and the angle between these three atoms (O=C—O) is 121.24 (9)°. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds and C—H⋯π interactions. The packing features wavy chains that extend parallel to [001]. International Union of Crystallography 2017-10-20 /pmc/articles/PMC5683502/ /pubmed/29152362 http://dx.doi.org/10.1107/S2056989017014670 Text en © Land et al. 2017 http://creativecommons.org/licenses/by/2.0/uk/ 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.http://creativecommons.org/licenses/by/2.0/uk/ |
spellingShingle | Research Communications Land, Michael A. Robertson, Katherine N. Clyburne, Jason A. C. Crystal structure of 2,4,6-trimethylbenzoic anhydride |
title | Crystal structure of 2,4,6-trimethylbenzoic anhydride |
title_full | Crystal structure of 2,4,6-trimethylbenzoic anhydride |
title_fullStr | Crystal structure of 2,4,6-trimethylbenzoic anhydride |
title_full_unstemmed | Crystal structure of 2,4,6-trimethylbenzoic anhydride |
title_short | Crystal structure of 2,4,6-trimethylbenzoic anhydride |
title_sort | crystal structure of 2,4,6-trimethylbenzoic anhydride |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5683502/ https://www.ncbi.nlm.nih.gov/pubmed/29152362 http://dx.doi.org/10.1107/S2056989017014670 |
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