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Crystallographic and spectroscopic characterization of 4-nitro-2-(trifluoromethyl)benzoic acid and 4-nitro-3-(trifluoromethyl)benzoic acid
The title compounds, both C(8)H(4)F(3)NO(4), represent two isomers of nitro trifluoromethyl benzoic acid. The compounds each contain a nitro functionality para to the carboxylic acid group, with the trifluoromethyl substituent ortho to the acid group in the 2-isomer and ortho to the nitro grou...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6509677/ https://www.ncbi.nlm.nih.gov/pubmed/31161068 http://dx.doi.org/10.1107/S2056989019003979 |
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author | Diehl III, George L. Je, Lisa Tanski, Joseph M. |
author_facet | Diehl III, George L. Je, Lisa Tanski, Joseph M. |
author_sort | Diehl III, George L. |
collection | PubMed |
description | The title compounds, both C(8)H(4)F(3)NO(4), represent two isomers of nitro trifluoromethyl benzoic acid. The compounds each contain a nitro functionality para to the carboxylic acid group, with the trifluoromethyl substituent ortho to the acid group in the 2-isomer and ortho to the nitro group in the 3-isomer. The regiochemistry with respect to the trifluoromethyl group results in steric interactions that rotate the carboxylic acid group or the nitro group out of the aromatic plane in the 2- and 3-isomer, respectively. Each molecule engages in intermolecular hydrogen bonding, forming head-to-tail dimers with graph-set notation R (2) (2)(8) and donor–acceptor hydrogen-bonding distances of 2.7042 (14) Å in the 2-isomer and 2.6337 (16) in the 3-isomer. Recrystallization attempts did not yield untwinned crystals. |
format | Online Article Text |
id | pubmed-6509677 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-65096772019-06-03 Crystallographic and spectroscopic characterization of 4-nitro-2-(trifluoromethyl)benzoic acid and 4-nitro-3-(trifluoromethyl)benzoic acid Diehl III, George L. Je, Lisa Tanski, Joseph M. Acta Crystallogr E Crystallogr Commun Research Communications The title compounds, both C(8)H(4)F(3)NO(4), represent two isomers of nitro trifluoromethyl benzoic acid. The compounds each contain a nitro functionality para to the carboxylic acid group, with the trifluoromethyl substituent ortho to the acid group in the 2-isomer and ortho to the nitro group in the 3-isomer. The regiochemistry with respect to the trifluoromethyl group results in steric interactions that rotate the carboxylic acid group or the nitro group out of the aromatic plane in the 2- and 3-isomer, respectively. Each molecule engages in intermolecular hydrogen bonding, forming head-to-tail dimers with graph-set notation R (2) (2)(8) and donor–acceptor hydrogen-bonding distances of 2.7042 (14) Å in the 2-isomer and 2.6337 (16) in the 3-isomer. Recrystallization attempts did not yield untwinned crystals. International Union of Crystallography 2019-03-29 /pmc/articles/PMC6509677/ /pubmed/31161068 http://dx.doi.org/10.1107/S2056989019003979 Text en © Diehl III et al. 2019 http://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.http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Research Communications Diehl III, George L. Je, Lisa Tanski, Joseph M. Crystallographic and spectroscopic characterization of 4-nitro-2-(trifluoromethyl)benzoic acid and 4-nitro-3-(trifluoromethyl)benzoic acid |
title | Crystallographic and spectroscopic characterization of 4-nitro-2-(trifluoromethyl)benzoic acid and 4-nitro-3-(trifluoromethyl)benzoic acid |
title_full | Crystallographic and spectroscopic characterization of 4-nitro-2-(trifluoromethyl)benzoic acid and 4-nitro-3-(trifluoromethyl)benzoic acid |
title_fullStr | Crystallographic and spectroscopic characterization of 4-nitro-2-(trifluoromethyl)benzoic acid and 4-nitro-3-(trifluoromethyl)benzoic acid |
title_full_unstemmed | Crystallographic and spectroscopic characterization of 4-nitro-2-(trifluoromethyl)benzoic acid and 4-nitro-3-(trifluoromethyl)benzoic acid |
title_short | Crystallographic and spectroscopic characterization of 4-nitro-2-(trifluoromethyl)benzoic acid and 4-nitro-3-(trifluoromethyl)benzoic acid |
title_sort | crystallographic and spectroscopic characterization of 4-nitro-2-(trifluoromethyl)benzoic acid and 4-nitro-3-(trifluoromethyl)benzoic acid |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6509677/ https://www.ncbi.nlm.nih.gov/pubmed/31161068 http://dx.doi.org/10.1107/S2056989019003979 |
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