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Planar versus non-planar: The important role of weak C—H⋯O hydrogen bonds in the crystal structure of 5-methylsalicylaldehyde
The crystal structure of 5-methylsalicylaldehyde (5-MSA; systematic name 2-hydroxy-5-methylbenzaldehyde), C(8)H(8)O(2), was discovered to be a textbook example of the drastic structural changes caused by just a few weak C—H⋯O interactions due to the additional methylation of the aromatic ring...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5290555/ https://www.ncbi.nlm.nih.gov/pubmed/28217332 http://dx.doi.org/10.1107/S2056989017000238 |
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author | Baisch, Ulrich Scicluna, Marie Christine Näther, Christian Vella-Zarb, Liana |
author_facet | Baisch, Ulrich Scicluna, Marie Christine Näther, Christian Vella-Zarb, Liana |
author_sort | Baisch, Ulrich |
collection | PubMed |
description | The crystal structure of 5-methylsalicylaldehyde (5-MSA; systematic name 2-hydroxy-5-methylbenzaldehyde), C(8)H(8)O(2), was discovered to be a textbook example of the drastic structural changes caused by just a few weak C—H⋯O interactions due to the additional methylation of the aromatic ring compared to salicylaldehyde SA. This weak intermolecular hydrogen bonding is observed between aromatic or methyl carbon donor atoms and hydroxyl or aldehyde acceptor oxygen atoms with d(D⋯A) = 3.4801 (18) and 3.499 (11) Å. The molecule shows a distorted geometry of the aromatic ring with elongated bonds in the vicinity of substituted aldehyde and hydroxyl carbon atoms. The methyl hydrogen atoms are disordered over two sets of sites with occupancies of 0.69 (2) and 0.31 (2). |
format | Online Article Text |
id | pubmed-5290555 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-52905552017-02-17 Planar versus non-planar: The important role of weak C—H⋯O hydrogen bonds in the crystal structure of 5-methylsalicylaldehyde Baisch, Ulrich Scicluna, Marie Christine Näther, Christian Vella-Zarb, Liana Acta Crystallogr E Crystallogr Commun Research Communications The crystal structure of 5-methylsalicylaldehyde (5-MSA; systematic name 2-hydroxy-5-methylbenzaldehyde), C(8)H(8)O(2), was discovered to be a textbook example of the drastic structural changes caused by just a few weak C—H⋯O interactions due to the additional methylation of the aromatic ring compared to salicylaldehyde SA. This weak intermolecular hydrogen bonding is observed between aromatic or methyl carbon donor atoms and hydroxyl or aldehyde acceptor oxygen atoms with d(D⋯A) = 3.4801 (18) and 3.499 (11) Å. The molecule shows a distorted geometry of the aromatic ring with elongated bonds in the vicinity of substituted aldehyde and hydroxyl carbon atoms. The methyl hydrogen atoms are disordered over two sets of sites with occupancies of 0.69 (2) and 0.31 (2). International Union of Crystallography 2017-01-13 /pmc/articles/PMC5290555/ /pubmed/28217332 http://dx.doi.org/10.1107/S2056989017000238 Text en © Baisch 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 Baisch, Ulrich Scicluna, Marie Christine Näther, Christian Vella-Zarb, Liana Planar versus non-planar: The important role of weak C—H⋯O hydrogen bonds in the crystal structure of 5-methylsalicylaldehyde |
title | Planar versus non-planar: The important role of weak C—H⋯O hydrogen bonds in the crystal structure of 5-methylsalicylaldehyde |
title_full | Planar versus non-planar: The important role of weak C—H⋯O hydrogen bonds in the crystal structure of 5-methylsalicylaldehyde |
title_fullStr | Planar versus non-planar: The important role of weak C—H⋯O hydrogen bonds in the crystal structure of 5-methylsalicylaldehyde |
title_full_unstemmed | Planar versus non-planar: The important role of weak C—H⋯O hydrogen bonds in the crystal structure of 5-methylsalicylaldehyde |
title_short | Planar versus non-planar: The important role of weak C—H⋯O hydrogen bonds in the crystal structure of 5-methylsalicylaldehyde |
title_sort | planar versus non-planar: the important role of weak c—h⋯o hydrogen bonds in the crystal structure of 5-methylsalicylaldehyde |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5290555/ https://www.ncbi.nlm.nih.gov/pubmed/28217332 http://dx.doi.org/10.1107/S2056989017000238 |
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