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Synthesis and crystal structure of a bench-stable pyridinium ketene hemiaminal: 1-(1-ethoxyethenyl)-2-[methyl(phenyl)amino]pyridin-1-ium trifluoromethanesulfonate
The novel bench-stable N-quaternized ketene N,O-acetal, C(16)H(19)N(2)O(+)·CF(3)O(3)S(−), was synthesized and its structure determined. The title compound is a rare example of a pyridinium ketene hemiaminal for which a crystal structure has been determined, joining the 2-chloro-1-(1-ethyoxyethenyl)...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10439406/ https://www.ncbi.nlm.nih.gov/pubmed/37601406 http://dx.doi.org/10.1107/S2056989023005741 |
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author | Krevlin, Zoe A. Bote, Isabella C. Crespo, Maria Christina F. Lam, Christie C. McMillen, Colin D. Majireck, Max M. |
author_facet | Krevlin, Zoe A. Bote, Isabella C. Crespo, Maria Christina F. Lam, Christie C. McMillen, Colin D. Majireck, Max M. |
author_sort | Krevlin, Zoe A. |
collection | PubMed |
description | The novel bench-stable N-quaternized ketene N,O-acetal, C(16)H(19)N(2)O(+)·CF(3)O(3)S(−), was synthesized and its structure determined. The title compound is a rare example of a pyridinium ketene hemiaminal for which a crystal structure has been determined, joining the 2-chloro-1-(1-ethyoxyethenyl)pyridin-1-ium trifluoromethanesulfonate salt from which it was synthesized. The cationic species of the title compound can be defined by three individually planar fragments assembling into a non-coplanar cation. The phenyl substituent extending from the amino nitrogen atom and the ethyoxyvinyl substituent extending from the pyridine N atom are oriented on the same side of the molecule and maintain the closest coplanar relationship of the three fragments. Supramolecular interactions are dominated by C—H⋯O interactions from the cation to the SO(3) side of the trifluoromethanesulfonate anion, forming a two-dimensional substructure. |
format | Online Article Text |
id | pubmed-10439406 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-104394062023-08-20 Synthesis and crystal structure of a bench-stable pyridinium ketene hemiaminal: 1-(1-ethoxyethenyl)-2-[methyl(phenyl)amino]pyridin-1-ium trifluoromethanesulfonate Krevlin, Zoe A. Bote, Isabella C. Crespo, Maria Christina F. Lam, Christie C. McMillen, Colin D. Majireck, Max M. Acta Crystallogr E Crystallogr Commun Research Communications The novel bench-stable N-quaternized ketene N,O-acetal, C(16)H(19)N(2)O(+)·CF(3)O(3)S(−), was synthesized and its structure determined. The title compound is a rare example of a pyridinium ketene hemiaminal for which a crystal structure has been determined, joining the 2-chloro-1-(1-ethyoxyethenyl)pyridin-1-ium trifluoromethanesulfonate salt from which it was synthesized. The cationic species of the title compound can be defined by three individually planar fragments assembling into a non-coplanar cation. The phenyl substituent extending from the amino nitrogen atom and the ethyoxyvinyl substituent extending from the pyridine N atom are oriented on the same side of the molecule and maintain the closest coplanar relationship of the three fragments. Supramolecular interactions are dominated by C—H⋯O interactions from the cation to the SO(3) side of the trifluoromethanesulfonate anion, forming a two-dimensional substructure. International Union of Crystallography 2023-07-07 /pmc/articles/PMC10439406/ /pubmed/37601406 http://dx.doi.org/10.1107/S2056989023005741 Text en © Krevlin et al. 2023 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 | Research Communications Krevlin, Zoe A. Bote, Isabella C. Crespo, Maria Christina F. Lam, Christie C. McMillen, Colin D. Majireck, Max M. Synthesis and crystal structure of a bench-stable pyridinium ketene hemiaminal: 1-(1-ethoxyethenyl)-2-[methyl(phenyl)amino]pyridin-1-ium trifluoromethanesulfonate |
title | Synthesis and crystal structure of a bench-stable pyridinium ketene hemiaminal: 1-(1-ethoxyethenyl)-2-[methyl(phenyl)amino]pyridin-1-ium trifluoromethanesulfonate |
title_full | Synthesis and crystal structure of a bench-stable pyridinium ketene hemiaminal: 1-(1-ethoxyethenyl)-2-[methyl(phenyl)amino]pyridin-1-ium trifluoromethanesulfonate |
title_fullStr | Synthesis and crystal structure of a bench-stable pyridinium ketene hemiaminal: 1-(1-ethoxyethenyl)-2-[methyl(phenyl)amino]pyridin-1-ium trifluoromethanesulfonate |
title_full_unstemmed | Synthesis and crystal structure of a bench-stable pyridinium ketene hemiaminal: 1-(1-ethoxyethenyl)-2-[methyl(phenyl)amino]pyridin-1-ium trifluoromethanesulfonate |
title_short | Synthesis and crystal structure of a bench-stable pyridinium ketene hemiaminal: 1-(1-ethoxyethenyl)-2-[methyl(phenyl)amino]pyridin-1-ium trifluoromethanesulfonate |
title_sort | synthesis and crystal structure of a bench-stable pyridinium ketene hemiaminal: 1-(1-ethoxyethenyl)-2-[methyl(phenyl)amino]pyridin-1-ium trifluoromethanesulfonate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10439406/ https://www.ncbi.nlm.nih.gov/pubmed/37601406 http://dx.doi.org/10.1107/S2056989023005741 |
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