Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Diehl III, George L., Je, Lisa, Tanski, Joseph M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
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
_version_ 1783417290178428928
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
work_keys_str_mv AT diehliiigeorgel crystallographicandspectroscopiccharacterizationof4nitro2trifluoromethylbenzoicacidand4nitro3trifluoromethylbenzoicacid
AT jelisa crystallographicandspectroscopiccharacterizationof4nitro2trifluoromethylbenzoicacidand4nitro3trifluoromethylbenzoicacid
AT tanskijosephm crystallographicandspectroscopiccharacterizationof4nitro2trifluoromethylbenzoicacidand4nitro3trifluoromethylbenzoicacid