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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 |
Sumario: | 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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