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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
Title: 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-stableN-quaternized keteneN,O-acetal, C16H19N2O+·CF3O3S−, 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 SO3side of the trifluoromethanesulfonate anion, forming a two-dimensional substructure.

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Award ID(s):
2155127
PAR ID:
10509675
Author(s) / Creator(s):
; ; ; ; ;
Publisher / Repository:
International Union of Crystallography
Date Published:
Journal Name:
Acta Crystallographica Section E Crystallographic Communications
Volume:
79
Issue:
8
ISSN:
2056-9890
Page Range / eLocation ID:
698 to 701
Subject(s) / Keyword(s):
crystal structure ketene hemiaminal N-quaternized ketene N,O-acetal.
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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