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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)...

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Autores principales: Krevlin, Zoe A., Bote, Isabella C., Crespo, Maria Christina F., Lam, Christie C., McMillen, Colin D., Majireck, Max M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2023
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.
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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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