6533b7cffe1ef96bd1258425
RESEARCH PRODUCT
NMR crystallography of 2-Acylamino-6-[1H]pyridones: solid state NMR, GIPAW computational, and single crystal X-ray diffraction studies
Miika LöfmanBorys OśmiałowskiKari AhonenSatu IkonenErkki Kolehmainensubject
Hydrogen bondCarbon-13 NMR satelliteChemistryChemical shiftOrganic ChemistryNuclear magnetic resonance spectroscopyNuclear magnetic resonance crystallographyTautomerAnalytical ChemistryInorganic ChemistryCrystallographySolid-state nuclear magnetic resonanceIntramolecular forceta116Spectroscopydescription
Abstract 2-Acylamino-6-[1H]-pyridones [acyl = RCO, where R = methyl (1), ethyl (2), iso-propyl (3), tert-butyl (4), and 1-adamantyl (5)] have been synthesized and characterized by NMR spectroscopy. From three congeners, 2, 3 and 5, also single crystal X-ray structures have been solved. For these derivatives GIPAW calculations acts as a “bridge” between solid-state NMR data and calculated chemical shifts based on X-ray determined geometry. In crystals all three compounds exist as pyridone tautomers possessing similar six-membered ring structure stabilized by intramolecular C O⋯HN hydrogen bond. Theoretical GIPAW calculated and experimental 13C and 15N CPMAS NMR shifts are in excellent agreement with each other.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2011-12-01 | Journal of Molecular Structure |