cg0c00689_si_001.pdf (14.31 MB)
Fluorinated Aminopyridines: Synthesis, Structure, and Rare Liquid–Liquid Cocrystal Formation Driven by Unusually Short N–H···F–C Hydrogen Bonding
journal contribution
posted on 2020-07-01, 13:33 authored by Andrew
J. Peloquin, Daniel A. Kure, Abby R. Jennings, Colin D. McMillen, Scott T. Iacono, William T. PenningtonThe
role of hydrogen bonding in the crystal packing of a series of 4-aminoperfluoropyridines
was studied using single-crystal X-ray crystallography. The aminoperfluoropyridines
were synthesized using only excess amine to serve as both nucleophile
and base. Instead of addition to the perfluoropyridine ring, a strong
N–H···F–C hydrogen bond led to cocrystal
formation of perfluoropyridine with sterically hindered amines dicyclohexylamine
as well as 2-methylpiperdine. This formation is, to our knowledge,
the first report of two nonreacting liquids, consisting of only discrete
small molecules, combining to form a cocrystalline solid stable under
ambient conditions. Perfluoropyridine is stabilized in the crystal
lattice approximately 100 °C above its normal boiling point.
History
Usage metrics
Categories
Keywords
nonreacting liquidscocrystalline4- aminoperfluoropyridinesambient conditionsFluorinated AminopyridinesstericallyBondingFormationseriesroleSynthesiRaremoleculesingle-crystal X-ray crystallographyUnusuallyperfluoropyridine ringPerfluoropyridinenucleophile2- methylpiperdinecrystal latticeamines dicyclohexylaminecocrystal formationCocrystalbond
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC