6533b836fe1ef96bd12a0195

RESEARCH PRODUCT

Self-Organization of 2-Acylaminopyridines in the Solid State and in Solution

Borys OśmiałowskiErkki KolehmainenReijo KauppinenArto ValkonenJuha KoivukorpiRobert DoboszKari RissanenRyszard Gawinecki

subject

Models MolecularSteric effectsMagnetic Resonance SpectroscopyChloroformMolecular StructureChemistryStereochemistryHydrogen bondIntermolecular forceAminopyridinesHydrogen BondingNuclear magnetic resonance spectroscopyCrystal structureCrystallography X-RaySolutionsCrystallographychemistry.chemical_compoundGroup (periodic table)MoleculeChloroformPhysical and Theoretical Chemistry

description

Aggregation of 2-acylaminopyridines and their 6-methyl derivatives in chloroform solution was studied by (1)H, (13)C, and (15)N NMR spectroscopies. The results were compared with (13)C and (15)N CPMAS NMR and IR spectral as well as with X-ray structural data. Intermolecular interactions in solution and in solid state were found to have a similar nature. Relatively strong N(amide)-H···N(pyridine) intermolecular hydrogen bonds enable dimerization to take place. Steric interactions in N-pivaloyl- and N-1-adamantylcarbonyl as well as that caused by the 6-methyl group hinder formation of the dimeric aggregates stabilized by the N(amide)-H···N(pyridine) intermolecular hydrogen bonds. In general, the DFT optimized geometries of the aggregates in chloroform solution are in agreement with the X-ray crystal structures. Wavenumbers of the stretching vibration band of the C═O group were also found indicative of the type of hydrogen bond present in the solid state.

yearjournalcountryeditionlanguage
2010-09-03The Journal of Physical Chemistry A
https://doi.org/10.1021/jp1063116